JP2010270065A - 光学活性トリフルオロメチル基含有化合物、その製造方法並びにそれを用いたトリフルオロメチル基含有光学活性アミン類の製造方法 - Google Patents
光学活性トリフルオロメチル基含有化合物、その製造方法並びにそれを用いたトリフルオロメチル基含有光学活性アミン類の製造方法 Download PDFInfo
- Publication number
- JP2010270065A JP2010270065A JP2009123457A JP2009123457A JP2010270065A JP 2010270065 A JP2010270065 A JP 2010270065A JP 2009123457 A JP2009123457 A JP 2009123457A JP 2009123457 A JP2009123457 A JP 2009123457A JP 2010270065 A JP2010270065 A JP 2010270065A
- Authority
- JP
- Japan
- Prior art keywords
- oxopyrazolidine
- dimethyl
- ethyl
- trifluoro
- naphthyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001412 amines Chemical class 0.000 title claims abstract description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 title abstract description 87
- 150000001875 compounds Chemical class 0.000 title description 8
- 238000000034 method Methods 0.000 title description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 53
- NDGRWYRVNANFNB-UHFFFAOYSA-N pyrazolidin-3-one Chemical class O=C1CCNN1 NDGRWYRVNANFNB-UHFFFAOYSA-N 0.000 claims abstract description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims abstract description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 6
- -1 4-methylphenylsulfonylmethyl group Chemical group 0.000 claims description 941
- 125000005469 ethylenyl group Chemical group 0.000 claims description 54
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
- 239000003444 phase transfer catalyst Substances 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 238000007142 ring opening reaction Methods 0.000 abstract description 2
- 229960003237 betaine Drugs 0.000 description 1898
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 76
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- 238000006243 chemical reaction Methods 0.000 description 75
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 64
- 239000004472 Lysine Substances 0.000 description 64
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 56
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 56
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 44
- 239000007787 solid Substances 0.000 description 41
- 238000002360 preparation method Methods 0.000 description 40
- 238000005160 1H NMR spectroscopy Methods 0.000 description 35
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 34
- AXSVSYJIFBUDFN-UHFFFAOYSA-N CC(C)(C1=C)NNC1=O Chemical compound CC(C)(C1=C)NNC1=O AXSVSYJIFBUDFN-UHFFFAOYSA-N 0.000 description 31
- 239000000047 product Substances 0.000 description 31
- DZGOYTKIUFZLAU-UHFFFAOYSA-N CC(C)(C(NN1)=C)C1=O Chemical compound CC(C)(C(NN1)=C)C1=O DZGOYTKIUFZLAU-UHFFFAOYSA-N 0.000 description 30
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 27
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 26
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- CMNKELODYNOSSU-UHFFFAOYSA-N 4-methylidenepyrazolidin-3-one Chemical compound C=C1CNNC1=O CMNKELODYNOSSU-UHFFFAOYSA-N 0.000 description 21
- 230000003287 optical effect Effects 0.000 description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 21
- 229960004592 isopropanol Drugs 0.000 description 19
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 18
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 17
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 15
- 125000001624 naphthyl group Chemical group 0.000 description 14
- RFPMGSKVEAUNMZ-UHFFFAOYSA-N pentylidene Chemical group [CH2+]CCC[CH-] RFPMGSKVEAUNMZ-UHFFFAOYSA-N 0.000 description 14
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 14
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 12
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 12
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 11
- BEUWBSAVSYYTEI-UHFFFAOYSA-N 5,5-dimethylpyrazolidin-3-one Chemical group CC1(C)CC(=O)NN1 BEUWBSAVSYYTEI-UHFFFAOYSA-N 0.000 description 11
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 10
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 9
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 9
- FJWJYHHBUMICTP-UHFFFAOYSA-N 4,4-dimethylpyrazolidin-3-one Chemical group CC1(C)CNNC1=O FJWJYHHBUMICTP-UHFFFAOYSA-N 0.000 description 9
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 9
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 9
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 description 8
- 125000006165 cyclic alkyl group Chemical group 0.000 description 8
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 8
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 7
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 6
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910001868 water Inorganic materials 0.000 description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- PCSPFEVKTGQATD-UHFFFAOYSA-N CC(C)(C1=C)N(C(C=C2)=CC=C2Br)NC1=O Chemical compound CC(C)(C1=C)N(C(C=C2)=CC=C2Br)NC1=O PCSPFEVKTGQATD-UHFFFAOYSA-N 0.000 description 4
- MBGFYWUTZNQJPB-UHFFFAOYSA-N CC(C)(C1=C)N(C(C=C2)=CC=C2F)NC1=O Chemical compound CC(C)(C1=C)N(C(C=C2)=CC=C2F)NC1=O MBGFYWUTZNQJPB-UHFFFAOYSA-N 0.000 description 4
- ZUUQREVIZAQYSY-UHFFFAOYSA-N CC(C)(C1=C)N(C(C=C2)=CC=C2OC)NC1=O Chemical compound CC(C)(C1=C)N(C(C=C2)=CC=C2OC)NC1=O ZUUQREVIZAQYSY-UHFFFAOYSA-N 0.000 description 4
- SPLQGPVHJBQTAM-UHFFFAOYSA-N CC(C)(C1=C)N(C2=C(C)C=CC=C2)NC1=O Chemical compound CC(C)(C1=C)N(C2=C(C)C=CC=C2)NC1=O SPLQGPVHJBQTAM-UHFFFAOYSA-N 0.000 description 4
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- NJQDFSUMGSSRHG-UHFFFAOYSA-N CC(C)(C1=C)N(C2=CC=C(C)C=C2)NC1=O Chemical compound CC(C)(C1=C)N(C2=CC=C(C)C=C2)NC1=O NJQDFSUMGSSRHG-UHFFFAOYSA-N 0.000 description 4
- BCZICMLAYFXJFP-UHFFFAOYSA-N CC(C)C(C=C1)=CC=C1N(C(C)(C)C1=C)NC1=O Chemical compound CC(C)C(C=C1)=CC=C1N(C(C)(C)C1=C)NC1=O BCZICMLAYFXJFP-UHFFFAOYSA-N 0.000 description 4
- 235000002597 Solanum melongena Nutrition 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 3
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XXQPEIJLGMWDJG-UHFFFAOYSA-N CC(C)(C)C(C=C1)=CC=C1N(C(C)(C)C1=C)NC1=O Chemical compound CC(C)(C)C(C=C1)=CC=C1N(C(C)(C)C1=C)NC1=O XXQPEIJLGMWDJG-UHFFFAOYSA-N 0.000 description 3
- DZWMNNLHEPDIMV-UHFFFAOYSA-N CC(C)(C1=C)N(C(C=C2)=CC=C2Cl)NC1=O Chemical compound CC(C)(C1=C)N(C(C=C2)=CC=C2Cl)NC1=O DZWMNNLHEPDIMV-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000006692 trifluoromethylation reaction Methods 0.000 description 3
- NVCOZPLAQFBPLM-NSHDSACASA-N 1-[(1S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl]-5,5-dimethylpyrazolidin-3-one Chemical compound CC1(C)CC(=O)NN1[C@H](C(F)(F)F)C1=CC=C(Br)C=C1 NVCOZPLAQFBPLM-NSHDSACASA-N 0.000 description 2
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- SFOVRQDEFYNDPM-UHFFFAOYSA-N 1-butoxy-3-prop-2-enylbenzene Chemical compound CCCCOC1=CC=CC(CC=C)=C1 SFOVRQDEFYNDPM-UHFFFAOYSA-N 0.000 description 2
- GLXYYHFXAQWLEP-UHFFFAOYSA-N 1-methoxy-3-prop-2-enylbenzene Chemical compound COC1=CC=CC(CC=C)=C1 GLXYYHFXAQWLEP-UHFFFAOYSA-N 0.000 description 2
- 125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
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- XVNOUKZWAPQHOK-NSHDSACASA-N 5,5-dimethyl-1-[(1S)-2,2,2-trifluoro-1-phenylethyl]pyrazolidin-3-one Chemical compound CC1(C)CC(=O)NN1[C@H](C(F)(F)F)C1=CC=CC=C1 XVNOUKZWAPQHOK-NSHDSACASA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
【解決手段】一般式(1)
(式中、R1及びR2は、水素原子又は炭素数1〜4のアルキル基を示し、R3は、炭素数1〜10のアルキル基、置換基を有してもよいフェニル基、置換基を有してもよい1−ナフチル基、置換基を有してもよい2−ナフチル基、置換基を有してもよいアリールエチレニル基又は置換基を有してもよいアリールアルキルを示す。)で表される光学活性3−オキソピラゾリジン誘導体、及び該オキソピラゾリジン誘導体を還元触媒で開環した後、酸で処理することによるトリフルオロメチル基を含有する光学活性アミン類の製造方法。
【選択図】なし
Description
[1] 下記一般式(1)
で表される光学活性3−オキソピラゾリジン誘導体。
で表される3−オキソピラゾリジン N,N−ベタイン誘導体とトリメチルシリルトリフルオロメタンをキラル相間移動触媒及び塩基の存在下、反応させることを特徴とする項1に記載された一般式(1)で表される光学活性3−オキソピラゾリジン誘導体の製造方法。
で表されることを特徴とする項2に記載の3−オキソピラゾリジン誘導体の製造方法。
で表される光学活性アミン類の製造方法を提供するものである。
ルオロ−1−(7−エトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ペントキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペントキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペントキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−オクチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ノニルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−デシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−フルオロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−フルオロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−フルオロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−フルオロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−フルオロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−クロロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−クロロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−クロロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−クロロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−クロロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ブロモ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ブロモ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ブロモ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ブロモ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ブロモ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−シアノ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−シアノ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−シアノ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフ
ルオロ−1−(6−シアノ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−シアノ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−シアノ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ニトロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ニトロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ニトロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ニトロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ニトロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン等を挙げることができる。
2,2,2−トリフルオロ−1−(4−エトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−tert−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ペントキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペントキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペントキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−オクチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ノニルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−デシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−フルオロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−フルオロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−フルオロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−フルオロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−フルオロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−クロロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−クロロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−クロロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−クロロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−クロロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−ブロモ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ブロモ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ブロモ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ブロモ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ブロモ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−シアノ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオ
ロ−1−(3−シアノ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−シアノ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−シアノ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−シアノ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−シアノ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−ニトロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ニトロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ニトロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ニトロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ニトロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン等を挙げることができる。
]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−シアノフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−シアノフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−シアノフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−ニトロフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−ニトロフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−ニトロフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ニトロフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ニトロフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ニトロフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−ニトロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−ニトロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−ニトロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−ニトロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−ニトロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−ニトロフェニル)ブチル]−3−オキソピラゾリジン等を挙げることができる。
−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−エトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ペントキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペントキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペントキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−オクチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ノニルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−デシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−フルオロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロ−
1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−フルオロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−フルオロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−フルオロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−フルオロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−クロロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−クロロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−クロロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−クロロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−クロロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ブロモ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ブロモ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ブロモ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ブロモ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ブロモ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−シアノ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−シアノ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−シアノ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−シアノ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−シアノ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−シアノ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ニトロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ニトロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ニトロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ニトロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ニトロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン等を挙げることができる。
4−n−デシル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−メトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−エトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−tert−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ペントキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペントキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペントキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−オクチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ノニルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−デシルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシルオキシ−2−ナフチル)−
1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−フルオロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−フルオロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−フルオロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−フルオロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−フルオロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−クロロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−クロロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−クロロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−クロロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−クロロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−ブロモ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ブロモ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ブロモ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ブロモ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ブロモ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−シアノ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−シアノ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−シアノ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−シアノ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−シアノ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−シアノ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−ニトロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ニトロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ニトロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ニトロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ニトロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン等を挙げることができる。
−[1−(トリフルオロメチル)−4−(2−ブロモフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−ブロモフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−ブロモフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−ブロモフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−ブロモフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−ブロモフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−シアノフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−シアノフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−シアノフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−シアノフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−シアノフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−シアノフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−シアノフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−シアノフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−シアノフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−シアノフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−シアノフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−シアノフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−ニトロフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−ニトロフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−ニトロフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ニトロフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ニトロフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ニトロフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−ニトロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−ニトロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−ニトロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−ニトロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−ニトロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−ニトロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン等を挙げることができる。
−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−エトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ペントキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペントキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペントキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−オクチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ノニルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−デシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−フルオロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロ
−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−フルオロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−フルオロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−フルオロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−フルオロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−クロロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−クロロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−クロロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−クロロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−クロロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ブロモ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ブロモ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ブロモ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ブロモ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ブロモ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−シアノ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−シアノ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−シアノ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−シアノ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−シアノ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−シアノ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ニトロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ニトロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ニトロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ニトロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ニトロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン等を挙げることができる。
4−n−デシル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−メトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−エトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−tert−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ペントキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペントキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペントキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−オクチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ノニルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−デシルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシルオキシ−2−ナフチル)−
1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−フルオロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−フルオロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−フルオロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−フルオロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−フルオロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−クロロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−クロロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−クロロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−クロロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−クロロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−ブロモ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ブロモ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ブロモ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ブロモ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ブロモ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−シアノ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−シアノ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−シアノ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−シアノ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−シアノ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−シアノ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−ニトロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ニトロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ニトロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ニトロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ニトロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン等を挙げることができる。
−[1−(トリフルオロメチル)−4−(2−ブロモフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−ブロモフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−ブロモフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−ブロモフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−ブロモフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−ブロモフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−シアノフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−シアノフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−シアノフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−シアノフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−シアノフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−シアノフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−シアノフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−シアノフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−シアノフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−シアノフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−シアノフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−シアノフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−ニトロフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−ニトロフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−ニトロフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ニトロフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ニトロフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ニトロフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−ニトロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−ニトロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−ニトロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−ニトロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−ニトロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−ニトロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン等を挙げることができる。
ラゾリジン N,N−ベタイン、1−[1−(8−n−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。
ラゾリジン N,N−ベタイン、1−[2−(8−n−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。
イン等をあげることができる。
オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリ
ジン N,N−ベタイン等を挙げることができる。
オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリ
ジン N,N−ベタイン等を挙げることができる。
ジン N,N−ベタイン、1−[3−(4−シアノフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−シアノフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−シアノフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−シアノフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−シアノフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−シアノフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−シアノフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−ニトロフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ニトロフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ニトロフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−ニトロフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−ニトロフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−ニトロフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−ニトロフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−ニトロフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−ニトロフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−ニトロフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−ニトロフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−ニトロフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。
オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、N,N−ベタイン、1−[1−(6−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−ニトロナフチル)]メチリデン−5,5−ジメチル−
3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。
オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリ
ジン N,N−ベタイン等を挙げることができる。
ジン N,N−ベタイン、1−[3−(4−シアノフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−シアノフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−シアノフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−シアノフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−シアノフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−シアノフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−シアノフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−ニトロフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ニトロフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ニトロフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−ニトロフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−ニトロフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−ニトロフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−ニトロフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−ニトロフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−ニトロフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−ニトロフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−ニトロフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−ニトロフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、等を挙げることができる。
本発明の一般式(4)で表わされる光学活性アミン類として、R3がメチル基、エチル基、炭素数3〜10の直鎖、分岐若しくは環式のアルキル基であるものとしては、具体的に例えば、(S)−1,1,1−トリフルオロ−2−アミノプロパン、(S)−1,1,1−トリフルオロ−2−アミノブタン、(S)−1,1,1−トリフルオロ−2−アミノペンタン、(S)−1,1,1−トリフルオロ−2−アミノ−3−メチルブタン、(S)−1,1,1−トリフルオロ−2−アミノヘプタン、(S)−1,1,1−トリフルオロ−2−アミノ−3,3−ジメチルブタン、(S)−1,1,1−トリフルオロ−2−アミノヘプタン、(S)−1,1,1−トリフルオロ−2−アミノオクタン、(S)−1,1,1−トリフルオロ−2−アミノ−3−シクロヘキシルエタン、(S)−1,1,1−トリフルオロ−2−アミノノナン、(S)−1,1,1−トリフルオロ−2−アミノデカン、(S)−1,1,1−トリフルオロ−2−アミノウンデカン、(S)−1,1,1−トリフルオロ−2−アミノドデカン等を挙げることができる。
オロ−1−(3−iso−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−iso−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−iso−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−iso−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−iso−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−iso−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−tert−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−tert−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−tert−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−tert−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−tert−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−tert−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−tert−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ペントキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ペントキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ペントキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ペントキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ヘキシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ヘプチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−オクチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ノニルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−デシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−デシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−デシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−デシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−フルオロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−フルオロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−フルオロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−フルオロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−フルオロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−フルオロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−フルオロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−クロロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−クロロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−クロロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−クロロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−クロロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−クロロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−クロロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−ブロモ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−ブロモ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−ブロモ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−ブロモ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−ブロモ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−ブロモ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−ブロモ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−シアノ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−シアノ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−シアノ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−シアノ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−シアノ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−シアノ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−シアノ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−ニトロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−ニトロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−ニトロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−ニトロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−ニトロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−ニトロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−ニトロ−1−ナフチル)−1−アミノエタン等を挙げることができる。
オロ−1−(3−iso−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−iso−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−iso−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−iso−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−iso−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−iso−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−tert−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−tert−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−tert−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−tert−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−tert−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−tert−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−tert−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−ペントキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ペントキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ペントキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ペントキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−ヘキシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−ヘプチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−オクチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−ノニルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−デシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−デシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−デシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−デシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−フルオロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−フルオロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−フルオロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−フルオロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−フルオロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−フルオロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−フルオロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−クロロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−クロロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−クロロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−クロロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−クロロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−クロロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−クロロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−ブロモ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−ブロモ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−ブロモ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−ブロモ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−ブロモ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−ブロモ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−ブロモ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−シアノ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−シアノ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−シアノ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−シアノ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−シアノ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−シアノ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−シアノ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−ニトロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−ニトロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−ニトロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−ニトロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−ニトロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−ニトロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−ニトロ−2−ナフチル)−1−アミノエタン等を挙げることができる。
参考文献1 Sibi,M.P.;Rane,D.;Stanley,L.M.;Soeta,T.Org.Lett.2008,10,2971−2974。
また、本発明の実施に当たって、下記キラル相間移動触媒A〜Pを使用した。
5,5−ジメチルピラゾリジン−3−オンの調製
攪拌子を備えた100mlのナス型フラスコに、3−メチルクロトン酸メチル(5.00g,43.81mmol)、ヒドラジン・1水和物(2.46g,49.10mmol)及びエタノール(70ml)を仕込み、還流下7時間反応を行った。
4,4−ジメチルピラゾリジン−3−オンの調製
攪拌子を備えた100mlのオートクレーブに、3−クロロ−2,2−ジメチルプロピオン酸クロリド(5.00g,32.46mmol)及びエタノール(70ml)を仕込み、0℃に冷却の後、これにトリエチルアミン(3.29g,32.46mmol)を5分かけて滴下した。
ピラゾリジン3−オンの調製
参考例1と同じ反応装置を用い、3−メチルクロトン酸メチルに替えて、アクリル酸メチル(5.00g,58.08mmol)に替えた以外、参考例1と同じ反応操作を行い目的物のピラゾリジン−3−オン(2.35g,27.30mmol)を得た(収率47%)。
1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,400MHz)δ1.76(s,6H),2.79(s,2H),7.04(s,1H),7.49−7.51(m,3H),8.35−8.38(m,2H)。
13C−NMR(CDCl3,100MHz)δ29.1,44.6,74.0,129.0,129.7,129.9,131.9,132.0,181.9。
IR(KBr)3064,2976,1661,1589,1451,1299,1180,1160,1091,944,889,862,808,762,694,674,642,613cm−1。
mp=140−142℃。
HRMS calcd. for C12H15N2O(M+H+):203.1179 Found: 203.1181。
1−ベンジリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1−ベンジリデン−3−オキソピラゾリジン N,N−ベタインの調製
1−(2−ナフチル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,200MHz)δ1.75(s,6H),2.77(s,2H),7.21(s,1H),7.46−7.60(m,2H),7.79−7.87(m,2H),7.94−7.98(m,1H),8.13(dd,J=1.8,8.6Hz,1H),9.15(s,1H)。
13C−NMR(CDCl3,150.9MHz)δ28.8,44.4,73.8,126.7,126.8,127.3,127.5,128.2,128.3,129.5,129.7,132.8,133.0,134.4。
IR(KBr)3057,2978,1660,1625,1580,1499,1472,1421,1314,1248,1171,1142,1092,991,923,881,814,758,671,652cm−1。
mp=200.5−202℃。
MS (EI,m/z)252(M+)。
1−(6−メトキシ−2−ナフチル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,200MHz)δ1.74(s,6H),2.77(s,2H),3.93(s,3H),7.10−7.20(m,3H),7.75(d,J=8.6Hz,1H),7.86(d,J=9.0Hz,1H),8.12(dd,J=1.9,8.5Hz,1H),9.04(s,1H)。
13C−NMR(CDCl3,150.9MHz)δ28.9,44.5,55.4,73.4,105.7,119.7,124.6,127.0,128.1,128.3,130.1,131.2,132.9,136.2,159.8,181.6。
IR(KBr)3055,2972,1658,1623,1587,1484,1425,1385,1320,1270,1221,1173,1147,1096,1025,919,845,809,666cm−1。
mp=183−185℃。
MS (EI,m/z)282(M+)。
1−(1−ナフチル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,200MHz)δ1.81(s,6H),2.78(s,2H),7.50−7.66(m,3H),7.87−7.94(m,3H),8.06(d,J=8.06Hz,1H),9.42(d,J=7.6Hz,1H)。
13C−NMR(CDCl3,150.9MHz)δ29.1,44.3,74.3,121.2,124.3,125.2,125.6,126.1,127.5,129.5,131.2,131.3,132.3,133.3,181.9。
IR(KBr)3040,2973,1651,1569,1508,1421,1310,1145,1100,1018,983,954,858,828,797,775,740,675,618cm−1。
mp=218−221℃。
MS(EI,m/z)252(M+)。
1−(2−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,200MHz)δ1.74(s,6H),2.50(s,3H),2.74(s,2H),7.20−7.35(m,4H),9.10−9.15(m,1H)。
13C−NMR(CDCl3,150.9MHz)δ19.7,29.0,44.2,73.9,126.5,126.7,127.7,130.3,131.2,131.5,138.0,181.6。
IR(KBr)3223,3066,2967,2873,2160,1659,1583,1565,1464,1315,1150,1082,949,875,763,677cm−1。
mp=161−162℃。
MS(EI,m/z)216(M+)。
1−(3−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,200MHz)δ1.72(s,6H),2.40(s,3H),2.73(s,2H),7.06(s,1H),7.25−7.39(m,2H),8.09(d,J=7.4Hz,1H),8.22(s,1H)。
13C−NMR(CDCl3,150.9MHz)δ21.3,28.8,44.4,73.6,128.5,129.0,129.4,130.0,131.9,132.7,138.6,181.6。
IR(KBr)3049,2971,1660,1591,1572,1457,1430,1373,1323,1303,1177,1139,1081,933,821,792,672cm−1。
mp=197−199℃。
MS(EI,m/z)216(M+)。
1−(4−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,200MHz)δ1.71(s,6H),2.40(s,3H),2.72(s,2H),7.07(s,1H),7.26(d,J=8.2Hz,2H),8.25(d,J=8.2Hz,2H)。
13C−NMR(CDCl3,100MHz)δ22.0,29.1,44.7,73.6,127.1,129.8,130.1,132.0,143.1,181.7。
IR(KBr)3056,2972,1656,1593,1558,1456,1435,1296,1180,1086,945,904,863,817,676,634cm−1。
mp=203−205℃。
HRMS calcd. for C13H17N2O +:217.1355 Found:217.1333。
1−(3−メトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,200MHz)δ1.73,(s,6H),2.73,(s,2H),3.85(s,3H),7.02(dd,J=2.5,7.7Hz,1H),7.09(s,1H),7.35(t,J=8.0Hz,1H),7.75(d,J=7.8Hz,1H),8.12(t,J=2.0Hz,1H)。
13C−NMR(CDCl3,50.3MHz)δ29.0,44.4,55.5,73.8,115.3,118.4,124.2,129.3,129.5,130.4,159.3,181.1。
IR(KBr)3044,3006,2969,1660,1585,1459,1412,1314,1293,1247,1164,1088,1045,984,957,788,672cm−1。
mp=137−139℃。
MS(EI,m/z)232(M+)。
1−(4−メトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,400MHz)δ1.68(s,6H),2.74(s,2H),3.85(s,3H),6.94(d,J=8.7Hz,2H),7.08(s,1H),8.33(d,J=8.7Hz,2H)。
13C−NMR(CDCl3,100MHz)δ29.1,44.9,55.7,73.1,114.4,122.7,129.8,134.0,162.6,181.5。
IR(KBr)3068,2983,1932,2840,1660,1606,1512,1439,1307,1259,1175,1085,1028,829,679cm−1。
mp=194−196℃。
HRMS calcd. for C13H17N2O2 +:233.1285 Found:233.1285。
1−(4−iso−プロピルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,200MHz)δ1.26(d,J=6.6Hz,6H),1.71(s,6H),2.73(s,2H),2.95(sept,J=6.9Hz,1H),7.08(s,1H),7.31(d,J=8.4Hz,2H),8.28(d,J=8.4Hz,2H)。
13C−NMR(CDCl3,50.3MHz)δ23.7,29.0,34.4,44.6,73.3,126.6,127.0,129.8,131.6,153.2,181.0。
IR(KBr)3404(br),3049,2962,2870,1658,1587,1557,1428,1310,1187,1144,1082,1018,949,835,723,677,632cm−1。
mp=185−187℃。
MS(EI,m/z)244(M+)。
1−(4−tert−ブチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,200MHz)δ1.33(s,9H),1.71(s,6H),2.73(s,2H),7.02(s,1H),7.48(d,J=8.6Hz,2H),8.27(d,J=8.8Hz,2H)。
13C−NMR(CDCl3,150.9MHz)δ28.8,30.9,35.1,44.5,73.3,125.7,126.8,129.8,131.6,155.7,181.4。
IR(KBr)2968,1663,1590,1555,1427,1311,1107,1083,948,885,826,692,677,642cm−1。
mp=225−227℃。
MS(EI,m/z)258(M+)。
1−(3,4−ジメチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,200MHz)δ1.71(s,6H),2.31(s,6H),2.72(s,2H),7.01(s,1H),7.21(d,J=7.8Hz,1H),8.06−8.11(m,2H)。
13C−NMR(CDCl3,150.9MHz)δ19.6,20.0,28.8,44.4,73.2,127.1,129.5,130.0,130.3,132.4,137.2,141.6,181.4。
IR(KBr)3056,2973,1655,1588,1507,1457,1428,1374,1308,1125,1079,929,861,822,712,674cm−1。
mp=204.5−206℃。
MS(EI,m/z)230(M+)。
1−(4−フルオロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,200MHz)δ1.73(s,6H),2.74(s,2H),7.06−7.19(m,3H),8.41(dd,J=5.7,6.6Hz,2H)。
13C−NMR(CDCl3,150.9MHz)δ28.7,44.3,73.7,115.9(d,J=21.1Hz),125.9(d,J=3.0Hz),128.7,134.1(d,J=9.1Hz),164.1(d,J=255.0Hz),181.6。
19F−NMR(CDCl3,188MHz)δ−104.7(s,1F)。
IR(KBr)3059,2978,1662,1598,1577,1506,1438,1374,1326,1306,1225,1163,1088,952,839,774,681,625cm−1。
mp=211−213℃
MS(EI,m/z)220(M+)。
1−(4−クロロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,400MHz)δ1.70(s,6H),2.72(s,2H),6.97(s,1H),7.40−7.43(dt,J=8.8,2.5Hz,2H),8.27−8.31(dt,J=8.8,2.5Hz,2H)。
13C−NMR(CDCl3,100MHz)δ29.1,44.5,74.3,127.7,128.2,129.2,132.8,137.9,181.9。
IR(KBr)3058,2977,1663,1587,1557,1490,1437,1329,1306,1288,1092,1014,950,831,688,674cm−1。
mp=199−201℃。
HRMS calcd. for C12H14ClN2O +:237.0789 Found:237.0784。
1−(4−ブロモフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,400MHz)δ1.70(s,6H),2.75(s,2H),7.02(s,1H),7.57−7.60(dt,J=8.8,2.5Hz,2H),8.20−8.23(dt,J=8.8,2.5Hz,2H)。
13C−NMR(CDCl3,100MHz)δ29.0,44.5,74.3,126.5,128.0,128.7,132.2,133.0,181.7。
IR(KBr)3049,2970,1669,1586,1552,1487,1464,1435,1399,1323,1308,1285,1089,819,706,678,653,623cm−1。
mp=197−197℃。
HRMS calcd. for C12H13BrN2NaO +:303.0103 Found:303.0096。
1−(3−フェニルプロピリデン−2−エン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,200MHz)δ1.65(s,6H),2.75(s,2H),6.92(d,J=9.6Hz,1H),7.09(d,J=16.2Hz,1H),7.35−7.38(m,3H),7.50−7.55(m,2H),7.66(dd,J=9.6,16.2Hz,1H)。
13C−NMR(CDCl3,150.9MHz)δ28.2,45.2,71.1,119.1,127.5,128.6,129.9,131.7,134.9,143.3,180.0。
IR(KBr)3024,2976,2933,1658,1597,1560,1335,1313,1254,1214,1174,1066,978,943,792,751,690,682cm−1。
mp=169.5,171.5℃。
MS(EI,m/z)228(M+)。
1−(シクロヘキシル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
1H−NMR(CDCl3,600MHz)δ1.22−1.40(m,5H),1.60(s,6H),1.69−1.76(m,3H),1.92−1.94(m,2H),2.69(s,2H),3.10−3.15(m,1H),6.42(d,J=7.2Hz,1H)。
13C−NMR(CDCl3,150.9MHz)δ24.7,25.4,28.2,28.6,37.6,45.9,71.6,140.6,180.2。
IR(KBr)3429(br),3033,2929,2854,1668,1595,1450,1340,1285,1235,1185,1146,1112,1062,968,946,897,809,774,680cm−1。
mp =94−97℃。
MS(EI,m/z)208(M+)。
(S)−1−(2,2,2−トリフルオロ−1−フェニル−1−エチル)−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.32(s,3H),1.48(s,3H),1.62,1.77(AB quartet,J=16.1Hz,2H),4.51(q,J=8.9Hz,1H),7.35−7.42(m,3H),7.46−7.51(m,2H),7.58(brs,1H)。
13C−NMR(CD3OD,150.9MHz)δ25.0,30.9,44.9,67.5(q,J=28.2Hz),67.6,127.7(q,J=280.2Hz),130.6,131.3,133.2,133.5,180.2。
19F−NMR(CDCl3,188MHz)δ−70.7(d,J=9.2Hz,3F)。
IR(KBr)3186,3086,2980,2929,1694,1497,1455,1360,1275,1242,1167,1124,1088,1033,898,846,710,658cm−1。
mp=191−192℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)252(M+)。
HRMS calcd. for C13H15F3N2O:272.1136 Found:272.1138。
光学純度(ee%)の決定は、ダイセル社製キラルカラムOJ−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5mL/min,λ=254nm,τmaj=16.9min,τmin=21.0min)。
[α]D 25=+41.1(c=0.27,MeOH),90%ee。
(S)−1−[2,2,2−トリフルオロ−1−(2−ナフト)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.34(s,3H),1.53(s,3H),1.62,1.76(AB quartet,J=16.0Hz,2H),4.68(q,J=8.7Hz,1H),7.49−7.60(m,4H),7.81−7.88(m,3H),7.96(s,1H)。
13C−NMR(CD3OD,150.9MHz)δ25.1,30.8,45.0,67.6(q,J=28.2Hz),67.7,127.8(q,J=280.2Hz),128.6,129.2,129.6,129.9,130.1,130.3,130.6,131.0,133.3,135.4,135.7,180.2。
19F NMR(CDCl3,188MHz)δ−70.4(d,J=7.9Hz,3F)。
IR(KBr)3176,3067,2985,2925,2855,1698,1598,1508,1418,1358,1272,1167,1122,1041,919,832,763,712,680cm−1。
mp=204−205.5℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)322(M+)。
HRMS calcd. for C17H17F3N2O:322.1293 Found:322.1302。
光学純度(ee%)は、ダイセル社製キラルカラムOJ−Hにより決定した(n−ヘキサン/2−プロパノール=90/10 vol/vol,流量1.0 mL/min,λ=254nm,τmaj=12.1min,τmin=8.0min)。
[α]D 25=+40.7(c=0.79,MeOH),90%ee。
(S)−1−[2,2,2−トリフルオロ−1−(2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.34(s,3H),1.53(s,3H),1.62,1.74(AB quartet,J=15.3Hz,2H),3.92(s,3H),4.64(q,J=8.9Hz,1H),7.11−7.20(m,2H),7.36(s,1H),7.54(d,J=8.4Hz,1H),7.74(d,J=7.8Hz,2H),7.86(s,1H)。
13C−NMR(CD3OD,150.9MHz)δ25.1,30.9,45.0,56.8,67.6(q,J=28.2Hz),67.6,107.4,121.5,127.9(q,J=280.2Hz),128.4,129.0,130.4,130.9,131.8,133.0,137.2,161.1,180.3。
19F−NMR(CDCl3,188MHz)δ−70.4(d,J=9.2Hz,3F)。
IR(KBr)3210,3064,2975,2848,2416,1696,1634,1607,1486,1400,1346,1276,1223,1152,1114,1033,853cm−1。
mp=205−206.5℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)352(M+)。
HRMS calcd. for C18H19F3N2O2:352.1399 Found:352.1387。
光学純度(ee%)は、ダイセル社製キラルカラムOD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5mL/min,λ=254nm,τmaj=31.5min,τmin=24.5min)。
[α]D 25=+44.3(c=0.37,MeOH),90%ee。
(S)−1−[2,2,2−トリフルオロ−1−(1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.21(s,3H),1.25(s,3H),1.65,1.98(AB quartet,J=16.2Hz,2H),5.40(q,J=8.3Hz,1H),7.20(s,1H),7.45−7.64(m,3H),7.90(d,J=8.2Hz,2H),8.02(t,J=6.6Hz,2H)。
13C−NMR(DMSO,150.9MHz)δ25.8,27.4,42.8,58.8−59.0(m),65.7,123.9,125.4,125.7(q,J=281.2Hz),126.3,127.4,128.4,129.5,129.7,130.0,131.8,134.0,176.5。
19F−NMR(CDCl3,188MHz)δ−69.3(d,J=7.9Hz,3F)。
IR(KBr)3147,3058,2846,1708,1671,1413,1350,1271,1158,1126,1033,1003,896,849,782,679cm−1。
mp=233−234℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)322(M+)。
HRMS calcd. for C17H17F3N2O:322.1293 Found:322.1284。
光学純度(ee%)は、ダイセル社製キラルカラムOJ−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5L/min,λ=254nm,τmaj=41.5min,τmin=21.4min)。
[α]D 25=−116.5(c=0.52,MeOH),93%ee。
(S)−1−[2,2,2−トリフルオロ−1−(2−メチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.21(s,3H),1.27(s,3H),1.94,2.15(ABquartet,J=16.1Hz,2H),2.41(s,3H),4.70(q,J=8.1Hz,1H),7.16−7.31(m,4H),7.78−7.81(m,1H)。
13C−NMR(CD3OD,150.9MHz)δ21.1,26.8,28.5,44.9,63.3(q,J=27.2Hz),67.6,127.6(q,J=280.7Hz),128.1,131.1,131.3,133.3,134.3,139.5,179.8。
19F−NMR(CDCl3,188MHz)δ−69.1(d,J=7.9Hz,3F)。
IR(KBr)3153,3067,2989,2849,1701,1674,1602,1473,1355,1266,1215,1160,1130,1042,929,894,735,654cm−1。
mp = 191.5−193℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)286(M+)。
HRMS calcd. for C14H17F3N2O:286.1293 Found:286.1289。
光学純度(ee%)は、ダイセル社製キラルカラムOD−Hにより決定した(n−ヘキサン/2−プロパノール=98/2 vol/vol,流量0.5mL/min,λ= 254nm,τmaj=30.7min,τmin=33.9min)。
[α]D 25=−8.3(c=0.64,MeOH),88%ee。
(S)−1−[2,2,2−トリフルオロ−1−(3−メチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.32(s,3H),1.46(s,3H),1.65,1.77(AB quartet,J=15.8Hz,2H),2.36(s,3H),4.46(q,J=8.8Hz,1H),7.21−7.30(m,5H)。
13C NMR(DMSO,150.9MHz)δ21.5,24.1,29.5,43.2,64.5(q,J=27.2Hz),65.3,125.8(q,J=280.7Hz),128.4,128.5,130.0,131.8,132.0,137.8,176.2。
19F−NMR(CDCl3,188MHz)δ−70.6(d,J=9.2Hz,3F)。
IR(KBr)3189,3076,2983,2927,1703,1605,1494,1417,1356,1275,1156,1125,1034,1000,944,822,788,719cm−1。
mp=198−201℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)286(M+)。
HRMS calcd. for C14H17F3N2O:286.1293 Found:286.1282。
光学純度(ee%)は、ダイセル社製キラルカラムOD−Hにより決定した(n−ヘキサン/2−プロパノール=98/2 vol/vol,流量0.5mL/min,λ=254nm,τmaj=24.4 min,τmin=26.4min)。
[α]D 25=+42.4(c=0.64,MeOH),94%ee。
(S)−1−[2,2,2−トリフルオロ−1−(4−メチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.32(s,3H),1.47(s,3H),1.64,1.75(ABquartet,J=15.8Hz,2H),2.35(s,3H),4.47(q,J=8.9Hz),7.18(d,J=8.2Hz,2H),7.28(s,1H),7.35(d,J=8.2Hz,2H)。
13C−NMR(CD3OD,150.9MHz)δ22.2,24.9,30.9,44.9,67.3(q,J=28.2Hz),67.5,127.7(q,J=279.7Hz),130.4,131.2,133.1,141.5,180.2。
19F−NMR(CDCl3,188MHz)δ−70.7(d,J=7.9Hz,3F)。
IR(KBr)3184,3077,2970,1693,1512,1420,1377,1363,1270,1174,1126,1036,1005,900,821,733,648cm−1。
mp=179−180℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)286(M+)。
HRMS calcd. for C14H17F3N2O:286.1293 Found:286.1304。
光学純度(ee%)は、ダイセル社製キラルカラムAD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5mL/min,λ=254nm,τmaj=16.3min,τmin=17.4min)。
[α]D 25=+39.0(c=0.49,MeOH),90%ee。
(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.32(s,3H),1.48(s,3H),1.71,1.79(ABquartet,J=16.0Hz,2H),3.79(s,3H),4.46(q,J=8.7Hz),6.90−6.96(m,1H),7.02−7.05(m,2H),7.25−7.34(m,1H),7.38−7.56(br,1H)。
13C−NMR(CD3OD,150.9MHz)δ25.0,30.8,45.0,56.8,67.4(q,J=27.9Hz),67.6,116.9,118.8,125.6,127.7(q,J=279.7Hz),131.6,134.9,162.0,180.3。
19F−NMR(CDCl3,188MHz)δ−70.6(d,J=9.2Hz,3F)。
IR(KBr)3186,3077,2979,2947,1701,1583,1494,1358,1297,1274,1247,1154,1119,1064,947,773,721cm−1。
mp=183−184 oC(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)302(M+)。
HRMS calcd. for C14H17F3N2O2:302.1242 Found:302.1269。
光学純度(ee%)は、ダイセル社製キラルカラムOD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量1.0mL/min,λ=254nm,τmaj=8.9min,τmin=12.1min)。
[α]D 25=+52.0(c=0.49,MeOH),92%ee。
(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.32(s,3H),1.47(s,3H),1.65,1.76(ABquartet,J=16.1Hz,2H),3.80(s,3H),4.46(q,J=8.9Hz,1H),6.86−6.94(m,2H),7.34(brs,1H),7.39(d,J=8.8Hz,2H)。
13C−NMR(CD3OD,150.9MHz)δ24.9,30.9,44.9,56.7,66.9(q,J=28.2Hz),67.4,116.0,125.1,127.8(q,J=280.2Hz),134.4,162.8,180.3。
19F−NMR(CDCl3,188MHz)δ−70.9(d,J=9.0Hz,3F)。
IR(KBr)3155,3059,2970,2841,1697,1610,1516,1471,1356,1308,1273,1252,1172,1111,1037,987,826cm−1。
mp=135−136.5℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)302(M+)。
HRMS calcd. for C14H17F3N2O2:302.1242 Found:302.1220。
光学純度(ee%)は、ダイセル社製キラルカラムAD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5mL/min,λ=254nm,τmaj=24.8min,τmin=26.4min)。
[α]D 25=+40.7(c=0.49,MeOH),95%ee。
(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロピルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.24(d,J=6.8Hz,6H),1.32(s,3H),1.47(s,3H),1.63,1.75(ABquartet,J=15.9Hz,2H),2.90(sept,J=6.9Hz,1H),4.47(q,J=8.8Hz,1H),7.22(d,J=9.0Hz,2H),7.28(brs,1H),7.88(d,J=8.2Hz,2H)。
13C−NMR(CD3OD,150.9MHz)δ24.9,25.3,30.9,36.0,44.9,67.3(q,J=28.2Hz),67.5,127.7(q,J=280.2Hz),128.6,130.8,133.2,152.4,180.2。
19F−NMR(CDCl3,188MHz)δ−70.7(d,J=9.2Hz,3F)。
IR(KBr)3206,3080,2971,1706,1614,1516,1462,1419,1357,1276,1159,1128,1035,902,830,748,665cm−1。
mp=113−116℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)314(M+)。
HRMS calcd. for C16H21F3N2O:314.1606 Found:314.1608。
光学純度(ee%)は、ダイセル社製キラルカラムAD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量1.0mL/min,λ=254nm,τmaj=6.7min,τmin=9.2min)。
[α]D 25=+40.4(c=0.53,MeOH),96%ee。
(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H NMR(CDCl3,200MHz)δ1.30(s,9H),1.32(s,3H),1.47(s,3H),1.64,1.76(ABquartet,J=15.9Hz,2H),4.47(q,J=8.9Hz,1H),7.38(s,5H)。
13C−NMR(CD3OD,150.9MHz)δ24.9,30.9,32.7,36.4,44.9,67.2(q,J=28.2Hz),67.4,127.5,127.7(q,J=280.2Hz),130.4,132.9,154.6,180.2。
19F NMR(CDCl3,188MHz)δ−70.7(d,J=9.2Hz,3F)。
IR(KBr)3187,3080,2973,1700,1508,1458,1419,1355,1274,1167,1120,1034,900,829,667cm−1。
mp=158.5−159.5 ℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)328(M+)。
HRMS calcd. for C17H23F3N2O:328.1762 Found:328.1771。
光学純度(ee%)は、ダイセル社製キラルカラムAD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5mL/min,λ=254nm,τmaj=12.9min,τmin=25.0min)。
[α]D 25=+40.5(c=0.49,MeOH),98%ee。
(S)−1−[2,2,2−トリフルオロ−1−(3,4−ジメチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.32(s,3H),1.47(s,3H),1.67,1.76(ABquartet,J=16.1Hz,2H),2.25(s,3H),2.26(s,3H),4.44(q,J=8.9Hz,1H),7.10−7.21(m,3H),7.55(br,1H)。
13C−NMR(CD3OD,150.9MHz)δ20.5,20.8,24.9,30.9,45.0,67.4(q,J=28.2Hz),67.5,127.8(q,J=280.2Hz),130.7,130.8,131.7,134.3,139.0,140.0,180.3。
19F−NMR(CDCl3,188MHz)δ−70.7(d,J=9.2Hz,3F)。
IR(KBr)3195,3081,2975,2928,1703,1507,1354,1278,1171,1119,852,812,785,730,652 cm−1。
mp=175−177 oC(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)300(M+)。
HRMS calcd. for C15H19F3N2O:300.1449 Found:300.1476。
光学純度(ee%)は、ダイセル社製キラルカラムAD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量1.0mL/min,λ=254nm,τmaj=7.4min,τmin=8.6min)。
[α]D 25=+45.8(c=0.40,MeOH) ,88%ee。
(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.32(s,3H),1.47(s,3H),1.63,1.82(ABquartet,J=16.0Hz,2H),4.51(q,J=8.7Hz,1H),7.04−7.13(m,2H),7.44−7.51(m,3H)。
13C−NMR(CD3OD,150.9MHz)δ25.1,30.8,45.0,66.7(q,J=28.2Hz),67.6,117.5(d,J=21.1Hz),127.6(q,J=279.7Hz),129.7(d,J=3.0Hz),135.2(d,J=7.5Hz),165.6(d,J=247.5Hz),180.2。
19F−NMR(CDCl3,188MHz)δ −110.7(tt,J=5.3,7.9Hz,1F),−70.9(d,J=7.7Hz,3F)。
IR(KBr)3179,3082,2971,2842,1692,1606,1510,1422,1364,1273,1231,1174,1125,1038,901,832,738,646cm−1。
mp=159−160℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)290(M+)。
HRMS calcd. for C13H14F4N2O:290.1042 Found:290.1053。
光学純度(ee%)は、ダイセル社製キラルカラムOD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5mL/min,λ=254nm,τmaj=15.8min,τmin=17.7min)。
[α]D 25=+34.0(c=0.55,MeOH),89% ee。
(S)−1−[2,2,2−トリフルオロ−1−(4−クロロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.32(s,3H),1.46(s,3H),1.66,1.83(ABquartet,J=16.2Hz,2H),4.49(q,J=8.7Hz,1H),7.34−7.45(m,4H),7.74(brs,1H)。
13C−NMR(CD3OD,150.9MHz)δ25.1,30.8,45.0,66.8(q,J=28.7Hz),67.7,127.5(q,J=280.2Hz),130.8,132.4,134.7,137.6,180.2。
19F−NMR(CDCl3,188MHz)δ−70.8(d,J=7.9Hz,3F)。
IR(KBr)3188,3080,2970,1692,1495,1272,1173,1126,1096,900,852,827,800,735,685,652cm−1。
mp=202−204 ℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)306(M+)。
HRMS calcd. for C13H14F3ClN2O:306.6747 Found:306.0749。
光学純度(ee%)は、ダイセル社製キラルカラムOJ−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量1.0 mL/min,λ=254nm,τmaj=9.5min,τmin=12.8min)。
[α]D 25=+35.1(c=0.60,MeOH),86% ee。
(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.32(s,3H),1.46(s,3H),1.66,1.83(ABquartet,J=16.0Hz,2H),4.48(q,J=8.6Hz,1H),7.33−7.38(m,3H),7.49−7.56(m,2H)。
13C NMR(CD3OD,150.9MHz)δ25.1,30.8,45.0,66.8(q,J=28.7Hz),67.7,125.7,127.5(q,J=280.2Hz),132.8,133.8,135.0,180.3。
19F−NMR(CDCl3,188MHz)δ−70.8(d,J=9.2Hz,3F)。
IR(KBr)3200,3079,2970,1693,1595,1491,1417,1362,1269,1173,1126,1076,1012,900,824,733,652cm−1。
mp=206−208℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS (EI,m/z)350,352(M+)。
HRMS calcd. for C13H14F3BrN2O:350.0242 Found:350.0233。
光学純度(ee%)は、ダイセル社製キラルカラムOJ−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5 mL/min,λ=254nm,τmaj=20.0min,τmin=26.6min)。
[α]D 25=+33.5(c=0.82,MeOH),83% ee。
(S)−1−[1−(トリフルオロメチル)−1−(3−フェニル−2−プロピレニル)]−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.33(s,3H),1.42(s,3H),2.04,2.47(ABquartet,J=16.3Hz,2H),4.06(dq,J=8.5,8.5Hz,1H),6.41(dd,J=9.2,16.2Hz,1H),6.78(d,J=16.2Hz,1H),7.28−7.41(m,5H),7.66(brs,1H)。
13C−NMR(CD3OD,150.9MHz)δ24.5,30.6,45.8,66.0(q,J=28.2Hz),67.0,119.9,127.5(q,J=279.7Hz),128.7,130.9,138.3,141.7,179.8。
19F NMR(CDCl3,188MHz)δ−72.5(d,J=7.9Hz,3F)。
IR(KBr)3204,3081,2982,1687,1473,1362,1267,1173,1127,1086,1034,1007,977,903,750,684,649cm−1。
mp=157−158.5℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)298(M+)。
HRMS calcd. for C15H17F3N2O:298.1293 Found:298.1302。
光学純度(ee%)は、ダイセル社製キラルカラムOJ−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5 mL/min,λ=254nm,τmaj=30.6min,τmin=22.4min)。
[α]D 25=+162.8(c=0.39,MeOH),79%ee。
(S)−1−(2,2,2−トリフルオロ−1−シクロヘキシルエチル)−5,5−ジメチル−3−オキソピラゾリジンの調製
1H−NMR(CDCl3,200MHz)δ1.14−1.25(m,5H),1.29(s,6H),1.64−1.91(m,6H),2.28,2.51(ABquartet,J =16.3Hz,2H),3.20(dq,J=4.1,9.0Hz,1H),7.68(brs,1H)。
13C−NMR(CD3OD,150.9MHz)δ26.9,28.3,28.4,28.5,30.1,32.0,33.0,40.3,45.9,65.1,67.3(q,J=23.6Hz),128.3(q,J=287.2Hz),178.0。
19F−NMR(CDCl3,188MHz)δ−66.1(d,J=9.2Hz,3F)。
IR(KBr)3155,3059,2930,2857,1689,1455,1350,1252,1157,1130,1102,1080,1047,771,702cm−1。
mp=158.5−159.5 ℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)278(M+)。
HRMS calcd. for C13H21F3N2O:278.1606 Found:278.1607。
光学純度(ee%)は、ダイセル社製キラルカラムAD−Hにより決定した(n−ヘキサン/2−プロパノール=98/2 vol/vol,流量0.5mL/min,λ= 254nm,τmaj=21.0min,τmin=25.1min)。
[α]D 25 =−54.4 (c=0.43,MeOH),71%ee。
(S)−2,2,2−トリフルロロ−1−フェニルエチルアミンの調製
1H−NMR(CDCl3,200MHz)δ1.01(s,3H),1.17(s,3H),2.21,2.35(ABquartet,J=15.3Hz,2H),2.24(brs,1H),4.20(q,J=7.7Hz,1H),5.69(br,1H),7.10(br,1H),7.36(s,5H)。
13C−NMR(CDCl3,150.9MHz)δ26.5,28.7,48.4,53.2,58.9(q,J=28.7Hz),125.5(q,J=280.7Hz),127.9,128.9,128.9,136.8,173.4。
19F−NMR(CDCl3,188MHz)δ−74.1(d,J=7.9Hz,3F)。
IR(KBr)3360,3264,2967,1667,1457,1396,1267,1149,1119,882,762,703,633cm−1。
mp=123−125℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)274(M+)。
HRMS calcd. for C13H17F3N2O:274.1293Found:274.1283。
10mLナスフラスコに中間体18b(30mg,0.109mmol)、濃塩酸を2.5mL加え100℃において2日間加熱撹拌した。室温に冷却後、減圧下において濃塩酸を留去すると白色固体が得られた。ジエチルエ−テルを用いてろ過を行い、ジエチルエーテルで固体を洗浄した。フリ−ズドライを行い、水を除去することで目的とするα−トリフルオロメチルアミンの塩酸塩18c(22.7mg,98%)を得た。得られた目的物の光学純度は89%eeで誘導による光学純度の低下は認められなかった。
1H−NMR(CD3OD,600MHz)δ5.41(q,J=6.0Hz,1H),7.56−7.62(m,5H)。
13C−NMR(CD3OD,150.9MHz)δ57.7(q,J=32.7Hz),125.8(q,J=280.2Hz),130.5,130.7,131.6,133.1。
19F−NMR(CD3OD,188MHz)δ−72.5(d,J=7.9Hz,3F)。
光学純度(ee%)は、ダイセル社製キラルカラムOD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5mL/min,λ=254nm,τmaj=22.8min,τmin=24.5min),89%ee。
実施例1で使用した1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインに替えて、参考例5で調製した1−ベンジリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタインを用い表1中に示した条件下、反応を行った。結果を表1中に示した。
実施例1で使用した1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインに替えて、参考例6で調製した1−ベンジリデン−3−オキソピラゾリジン N,N−ベタインを用い、水酸化カリウムムに替えて表2中に表示の塩基を用い、ジクロロメタン単独溶媒中で反応を行った。結果を表2中に示した。
実施例1で使用した1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインに替えて、参考例6で調製した1−ベンジリデン−3−オキソピラゾリジン N,N−ベタインを用い、トリメチルシリルトリフルオロメタン(2.0モル)、表3中に示したキラル相間移動触媒(10mol%)、水酸化カリウム(0.2モル)、ジクロロメタン単独溶剤で室温下、反応を行った。結果を表3中に示した。
実施例1と同じ反応装置を用い、参考例1で調製した1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、キラル相間移動触媒A(10モル%)、トリメチルシリルトリフルオロメタン(10モル)、水酸化カリウム(6.0モル)を用い、表4中に示した溶剤に変更し反応を行った。結果を表4中に示した。
実施例1と同じ反応装置を用い、参考例1で調製した1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを用い、溶剤トルエン/ジクロロメタン=2/1で、表5中の示した条件下、−50℃で反応を行った。結果を表5中に示した。
実施例15で調製した光学活性なトリフルオロメチル化物15bについて、X線結晶構造解析を行い、生成物の絶対配置が(S)体であることを確認した。
Claims (4)
- 下記一般式(1)
(式中、R1及びR2はそれぞれ独立に水素原子又は、炭素数1〜4のアルキル基を示し、R3は炭素数1〜10のアルキル基、置換基を有しても良いフェニル基、置換基を有しても良い1−ナフチル基、置換基を有しても良い2−ナフチル基、置換基を有しても良いアリールエチレニル基又は置換基を有しても良いアリールアルキルを示す)
で表される光学活性3−オキソピラゾリジン誘導体。 - 下記一般式(2)
(式中R1、R2及びR3は前記に同じ)
で表される3−オキソピラゾリジン N,N−ベタイン誘導体とトリメチルシリルトリフルオロメタンをキラル相間移動触媒及び塩基の存在下、反応させることを特徴とする請求項1に記載された一般式(1)で表される光学活性3−オキソピラゾリジン誘導体の製造方法。 - 請求項2において、キラル相間移動触媒が下記一般式(3)
(式中R4は水素原子またはメトキシ基、R5は水素原子または4−メチルフェニルスルホニルメチル基、R6はエチル基またはエチレニル基、R7及びR8は各々独立して、水素原子、メチル基、エチル基、iso−プロピル基、tert−ブチル基、メトキシ基、エトキシ基、iso−プロポキシ基、tert−ブトキシ基、フェニル基、3,5−ビス(トリフルオロメチル)フェニル基、1−ナフチル基を示し、Xは塩素原子または臭素原子を示す)
で表されることを特徴とする請求項2に記載の製造方法。 - 請求項1に記載された一般式(1)で表される光学活性3−オキソピラゾリジン誘導体を還元触媒で開環した後、酸で処理することを特徴とする下記一般式(4)
(R3は前記に同じ)
で表される光学活性アミン類の製造方法。
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| JPS5182272A (en) * | 1974-12-11 | 1976-07-19 | Agfa Gevaert Nv | 44 monoharo 22 pirazorin 55 onkagobutsuno seizoho |
| JP2006521393A (ja) * | 2003-03-26 | 2006-09-21 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 2−置換−5−オキソ−3−ピラゾリジンカルボキシレートの製造および使用 |
| JP2010270064A (ja) * | 2009-05-21 | 2010-12-02 | Nagoya Institute Of Technology | ピラゾリジン−3−オン誘導体の製造方法 |
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|---|---|---|---|---|
| JPS5182272A (en) * | 1974-12-11 | 1976-07-19 | Agfa Gevaert Nv | 44 monoharo 22 pirazorin 55 onkagobutsuno seizoho |
| JP2006521393A (ja) * | 2003-03-26 | 2006-09-21 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 2−置換−5−オキソ−3−ピラゾリジンカルボキシレートの製造および使用 |
| JP2010270064A (ja) * | 2009-05-21 | 2010-12-02 | Nagoya Institute Of Technology | ピラゾリジン−3−オン誘導体の製造方法 |
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