SU1766922A1 - 2-(4-carboxy-3-halogenphenyl)-5-alkyl-1,3,2-dioxaborinanes as semiproducts for synthesis of liquid-crystalline derivatives of halogen-pnenyl-5-alkyl-1,3,2-dioxaborinanes - Google Patents
2-(4-carboxy-3-halogenphenyl)-5-alkyl-1,3,2-dioxaborinanes as semiproducts for synthesis of liquid-crystalline derivatives of halogen-pnenyl-5-alkyl-1,3,2-dioxaborinanes Download PDFInfo
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- SU1766922A1 SU1766922A1 SU864162761A SU4162761A SU1766922A1 SU 1766922 A1 SU1766922 A1 SU 1766922A1 SU 864162761 A SU864162761 A SU 864162761A SU 4162761 A SU4162761 A SU 4162761A SU 1766922 A1 SU1766922 A1 SU 1766922A1
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- alkyl
- carboxy
- dioxaborinanes
- synthesis
- halogen
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- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 11
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 5
- 239000000543 intermediate Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 238000000921 elemental analysis Methods 0.000 claims description 2
- 230000007704 transition Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- 239000013078 crystal Substances 0.000 abstract description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 11
- -1 (4-Cyanophenyloxycarbonyl) -3-fluorophenyl-5-propyl-1,3,2-di-oxaborinan Chemical compound 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-MICDWDOJSA-N 1-deuteriopropan-2-one Chemical compound [2H]CC(C)=O CSCPPACGZOOCGX-MICDWDOJSA-N 0.000 description 1
- FZHZPYGRGQZBCV-UHFFFAOYSA-N 2-propylpropane-1,3-diol Chemical compound CCCC(CO)CO FZHZPYGRGQZBCV-UHFFFAOYSA-N 0.000 description 1
- CZDWJVSOQOMYGC-UHFFFAOYSA-N 4-borono-2-fluorobenzoic acid Chemical compound OB(O)C1=CC=C(C(O)=O)C(F)=C1 CZDWJVSOQOMYGC-UHFFFAOYSA-N 0.000 description 1
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- MDXOASINEVOWCV-UHFFFAOYSA-N 5-butyl-2,5-dimethoxycyclohexa-1,3-diene Chemical compound CCCCC1(OC)CC=C(OC)C=C1 MDXOASINEVOWCV-UHFFFAOYSA-N 0.000 description 1
- 240000004760 Pimpinella anisum Species 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- Liquid Crystal Substances (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Изобретение касаетс бороорганиче- ских веществ, в частности 2-(4-карбокси-3- галогенфенил)-5-алкил-1,3,2-диоксаборина- нов общей ф-лы с„На,-О-©-ск °н , О Х где п 3 или 5 при Х- CI; , 6, 7 при X-F-, полупродуктов синтеза жидкокристаллических производных галогенфенил-5-алкил- 1,3,2-диоксаборинанов, обладающих более высокими значени ми положительной диэлектрической анизотропии и более низкими температурами образовани нематической фазы. Цель - создание новых полупродуктов с достижением лучших указанных свойств дл конечных веществ. Синтез ведут из 2-(4- карбокси-3-фторфенил)борной кислоты и 2- алкил-1,3-пропандиола в среде ацетона при кип чении. Выход, т пл. или т. интервал л существовани нематической фазы °С; § брутто-ф-ла: а) 88; 186; CisHieBFCM; б) 73; iT 183; Ci3Hi6BCI04; в) 82; 164-169; СЛ Ci4Hi8BF04; г) 76; 156-174; CisHaoBFOo; д) Г 69; 118-123; Ci5H2oBCl04; e) 64; 158; Г С1бН22ВР04;ж)72-147-169; C17H24BFCM. 2 табл. The invention relates to boroorganic substances, in particular, 2- (4-carboxy-3-halophenyl) -5-alkyl-1,3,2-dioxaborinans in common f-crystals with "Na, -O-S-C" n, O X where p 3 or 5 with X - CI; , 6, 7 in the case of X-F-, intermediates for the synthesis of liquid-crystal derivatives of halogen-phenyl-5-alkyl-1,3,2-dioxaborinan, which have higher values of positive dielectric anisotropy and lower temperatures for the formation of the nematic phase. The goal is to create new intermediates with the achievement of the best of these properties for the final substances. Synthesis of lead from 2- (4-carboxy-3-fluorophenyl) boric acid and 2-alkyl-1,3-propanediol in acetone at boiling. Exit, t pl. or the interval of the existence of the nematic phase of & § gross-la: a) 88; 186; CisHieBFCM; b) 73; iT 183; Ci3Hi6BCI04; c) 82; 164-169; SL Ci4Hi8BF04; d) 76; 156-174; CisHaoBFOo; e) D 69; 118-123; Ci5H2oBCl04; e) 64; 158; G S1bN22VR04; g) 72-147-169; C17H24BFCM. 2 tab.
Description
Изобретение относитс к новым соединени м , а именно к 2-(4-карбокси-3-галоген- фенил)-5-алкил-1,3,2-диоксаборинанам, которые могут найти применение в качестве полупродуктов синтеза новых жидкокристаллических соединений, предназначенных дл использовани в электрооптических устройствах отображени информации .The invention relates to new compounds, namely to 2- (4-carboxy-3-halogen-phenyl) -5-alkyl-1,3,2-dioxaborinan, which can be used as intermediates for the synthesis of new liquid-crystalline compounds intended for use in electro-optical information display devices.
Цель изобретени - изыскание новых полупродуктов, которые обеспечивают получение жидкокристаллических соединений, обладающих более высокими значени ми положительной диэлектрической анизотропии и более низкими температурами образовани нематической фазы по сравнению с известными соединени ми.The purpose of the invention is to find new intermediates that provide liquid crystal compounds with higher values of positive dielectric anisotropy and lower temperatures for the formation of the nematic phase compared with the known compounds.
Пример 1. 2-(4-Карбокси-3-ф|Ср Ье- нил)-5-пропил-1,3,2-диоксаборинан.Example 1. 2- (4-Carboxy-3-f | Cp Len) -5-propyl-1,3,2-dioxaborinan.
Смесь 4,3 г (0,025 моль) 4-карбокси-З- фторфенилборной кислоты, 3,0 г (0,025 моль) 2-пропил-1,3-пропандиола в 70 мл ацетона кип тили в колбе с обратным холодильником 5 ч, Растаооитель отгон ли, продукт кристаллизовали из метилэтилкетсна. Выход 5,7 г (0,022 моль), 88%, т, пл. 195°С.A mixture of 4.3 g (0.025 mol) of 4-carboxy-3-fluorophenylboronic acid, 3.0 g (0.025 mol) of 2-propyl-1,3-propanediol in 70 ml of acetone was boiled in a flask with a reflux condenser for 5 h. Distilled off, the product was crystallized from methyl ethyl ketone. The output of 5.7 g (0,022 mol), 88%, t, pl. 195 ° C.
XIXi
ОABOUT
Os ЮOs Yu
hOhO
юYu
Аналогично получены и другие кислоты, выходы и температуры фазовых переходов которых представлены втабл, 1.Similarly, other acids were obtained, the yields and temperatures of phase transitions of which are presented in table, 1.
Состав и строение полученных соединений подтверждены результатами элемент- ного анализа (табл 1). данными ИК-, ПМР-спектров.The composition and structure of the compounds obtained are confirmed by the results of elemental analysis (Table 1). data IR, PMR spectra.
Так, в спектрах JIMP предлагаемых соединений (10%-ный раствор в дейтероацето- не, эталон - ГМДС, прибор Tesla BS-467, б, м.д.) сигналы атомов водорода диоксабо- ринанового фрагмента наблюдаютс в области 3, 4-4,3 (центры при 3,54, 3,70, 3,86, 4,00, 4,10, 4,16, 4,26). Сигналы атомов водорода бензольного кольца наблюдаютс в области 7,10-7,83. В ИК-спектрах соединений (0,1 М растворы в CCI/j, хролоформе) интенсивный пик 1715 см соответствует валентным колебани м карбонила карбоксильного фрагмента.Thus, in the JIMP spectra of the proposed compounds (10% solution in deuteroacetone, standard - HMDS, Tesla BS-467, b, ppm), the signals of the hydrogen atoms of the dioxaborinan fragment are observed in the range of 3, 4–4 , 3 (centers at 3.54, 3.70, 3.86, 4.00, 4.10, 4.16, 4.26). Signals of hydrogen atoms of the benzene ring are observed in the range of 7.10-7.83. In the IR spectra of compounds (0.1 M solutions in CCI / j, hroloform), an intense peak of 1715 cm corresponds to the stretching vibrations of the carbonyl of the carboxyl moiety.
Синтезирование соединени - при комнатной температуре белые, без запаха кристаллы .JSynthesizing the compound — white, odorless crystals at room temperature .J
На основе 2-(4-карбокси-3-галогенфе- нил)-5-алкил-1,3,2-диоксаборинанов были получены жидкокристаллические эфиры (табл. 2), величины положительной диэлектрической анизотропии и температуры образовани нематической фазы которых были сопоставлены с аналогичными параметра- ми соответствующих эфиров аналога (табл. 2).Based on 2- (4-carboxy-3-halogenophenyl) -5-alkyl-1,3,2-dioxaborinan, liquid crystal ethers were obtained (Table 2), the values of the positive dielectric anisotropy and the temperature of formation of the nematic phase were compared to similar parameters of the corresponding analogue esters (Table 2).
Пример 2. (4-Цианофенилокси- карбонил)-3-фторфенил -5-пропил-1,3,2-ди - оксаборинан.Example 2. (4-Cyanophenyloxycarbonyl) -3-fluorophenyl-5-propyl-1,3,2-di-oxaborinan.
Смесь 1 г (0,004 моль) 2-(4-карбокси-3- фторфенил)-5-пропил-1,3,2-диоксаборина - на, 0,32 мл пиридина, 0,32 мл тионила хлористого в 50 мл безводного диэтилового эфира перемешивали 1 ч. Затем добавл ли 0,5 г (0,004 моль) 4-оксибензонитрила и 1 мл пиридина. Смесь оставл ли на ночь, фильтровали . Остаток, полученный после отгонки растворител , кристаллизовали из гексана, этилового спирта. Выход 1 г (0,0027 моль), 67,5%, температурна область существовани немчтической фазы 89- 174°С.A mixture of 1 g (0.004 mol) of 2- (4-carboxy-3-fluorophenyl) -5-propyl-1,3,2-dioxaborin, 0.32 ml of pyridine, 0.32 ml of thionyl chloride in 50 ml of anhydrous diethyl the ester was stirred for 1 hour. Then 0.5 g (0.004 mol) of 4-hydroxybenzonitrile and 1 ml of pyridine were added. The mixture was left overnight, filtered. The residue obtained after distilling off the solvent was crystallized from hexane, ethyl alcohol. Yield 1 g (0.0027 mol), 67.5%, the temperature range of the non-chemical phase is 89-174 ° C.
Аналогично были получены и другие эфиры.Similarly, other esters were obtained.
Определение температур образовани нематической фазы, измерени положительной диэлектрической анизотропии эфиров , полученных на основе предлагаемых соединений, и сопоставление, приведенное в табл. 2, этих данных с результатами ана- логичных измерений соответствующих эфиров прототипа показало, что жидкокристаллические соединени , синтезированные на основе предлагаемых кислот, характеризуютс более высокимиThe determination of the temperature of the formation of the nematic phase, the measurement of the positive dielectric anisotropy of the esters obtained on the basis of the proposed compounds, and the comparison given in Table. 2, these data with the results of similar measurements of the corresponding prototype ethers showed that liquid crystal compounds synthesized on the basis of the proposed acids are characterized by higher
значени ми положительной диэлектрической анизотропии, более низкими температурами образовани нематической фазы, чем те же производные аналога.values of positive dielectric anisotropy, lower temperatures for the formation of the nematic phase than the same derivatives of the analog.
Дл дополнительного подтверждени преимущества предлагаемых кислот по сравнению с аналогом были приготовлены смеси, содержащие 15 мае. ч. (4-циано- фенилоксикарбонил)-3-галогенфенил -5-ал- кил-1,3,2-диоксаборинана (эфиры, полученные на основе предлагаемых кислот) и 85 мае. ч, состава (А), состо щего из 2 мае, ч. 4-бутил-4-метоксианизола и 1 мае. ч, 4-бу- тил-4-гексилкарбоксибензола, а также смеси, содержащие 15 мае. ч. (4-циано- фенилоксикарбонил)фенил -5-алкил-1,3,2- диоксаборинана (эфиры, полученные на основе прототипа) и 85 мае. ч. состава (А). Результаты измерений диэлектрической анизотропии полученных смесей подтвердили преимущество предлагаемых кислот по сравнению с аналогом.To further confirm the advantage of the proposed acids over the analog, mixtures containing 15 May were prepared. including (4-cyanophenyloxycarbonyl) -3-halophenyl-5-alkyl-1,3,2-dioxaborinan (esters obtained from the proposed acids) and 85 May. composition (A) consisting of 2 May, including 4-butyl-4-methoxyanisole and 1 May. h, 4-butyl-4-hexylcarboxybenzene, as well as mixtures containing 15 May. including (4-cyanophenyloxycarbonyl) phenyl-5-alkyl-1,3,2-dioxaborinan (esters derived from the prototype) and 85 May. including composition (A). The results of measurements of the dielectric anisotropy of the mixtures obtained confirmed the advantage of the proposed acids over the analog.
рическа ани смесей, полуна основе эфилагаемых anis mixtures
80 5,9 6,4 5,5 3,8 4,5 4,080 5.9 6.4 5.5 3.8 4.5 4.0
Диэлектрическа анизотропи смесей, полученных на основе эфиров прототипаDielectric anisotropy of mixtures derived from prototype esters
6,26.2
4,74.7
3,83.8
3,03.0
2,32.3
Результаты даютс в последовательност х , аналогичных приведенным в табл. 2 описани изобретени .Results are given in sequences similar to those shown in Table. 2 description of the invention.
Таким образом, предлагаемые 2-(4-кар- бокси-3-галогенфенил)-5-алкил-1,3,2-диокс аборинаны по сравнению с аналогом обладают тем преимуществом, что на их основе могут быть получены жидкокристаллические соединени с более высокими значени- ми положительной диэлектрической анизотропии, более низкими температурами образовани нематической фазы, которые с успехом найдут применение в электрооптических устройствах отображени информации.Thus, the proposed 2- (4-carboxy-3-halophenyl) -5-alkyl-1,3,2-diox aborinans have the advantage in comparison with the analog that they can be obtained on the basis of liquid crystals with higher values of positive dielectric anisotropy, lower temperatures of formation of the nematic phase, which will successfully find application in electro-optical information display devices.
Claims (1)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU864162761A SU1766922A1 (en) | 1986-12-17 | 1986-12-17 | 2-(4-carboxy-3-halogenphenyl)-5-alkyl-1,3,2-dioxaborinanes as semiproducts for synthesis of liquid-crystalline derivatives of halogen-pnenyl-5-alkyl-1,3,2-dioxaborinanes |
| CH4887/87A CH671400A5 (en) | 1986-12-17 | 1987-12-15 | |
| GB8729239A GB2201150B (en) | 1986-12-17 | 1987-12-15 | 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaborinane derivatives and liquid crystal material |
| FR878717599A FR2608608B1 (en) | 1986-12-17 | 1987-12-16 | DERIVATIVES OF 2- (4,3-PHENYL DISUBSTITUTED) 5-ALKYL-1, 3, 2-DIOXABORINANE AND NEMATIC MATERIAL |
| US07/133,635 US4853150A (en) | 1986-12-17 | 1987-12-16 | 2-(4,3-Disubstituted phenyl)-5-alkyl-1,3,2-dioxaborinane derivatives and liquid crystal material |
| JP62316338A JPS63215682A (en) | 1986-12-17 | 1987-12-16 | 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2- dioxabolinane derivative and liquid crystal material |
| CN198787108378A CN87108378A (en) | 1986-12-17 | 1987-12-17 | liquid crystal material |
| DE19873742885 DE3742885A1 (en) | 1986-12-17 | 1987-12-17 | 2- (4,3-DISUBSTITUTED PHENYL) -5-ALKYL-1,3,2-DIOXABORINE ANDERIVATIVES AND LIQUID CRYSTALINE MATERIAL |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU864162761A SU1766922A1 (en) | 1986-12-17 | 1986-12-17 | 2-(4-carboxy-3-halogenphenyl)-5-alkyl-1,3,2-dioxaborinanes as semiproducts for synthesis of liquid-crystalline derivatives of halogen-pnenyl-5-alkyl-1,3,2-dioxaborinanes |
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| Publication Number | Publication Date |
|---|---|
| SU1766922A1 true SU1766922A1 (en) | 1992-10-07 |
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| Application Number | Title | Priority Date | Filing Date |
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| SU864162761A SU1766922A1 (en) | 1986-12-17 | 1986-12-17 | 2-(4-carboxy-3-halogenphenyl)-5-alkyl-1,3,2-dioxaborinanes as semiproducts for synthesis of liquid-crystalline derivatives of halogen-pnenyl-5-alkyl-1,3,2-dioxaborinanes |
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| Country | Link |
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| JP (1) | JPS63215682A (en) |
| SU (1) | SU1766922A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2122541C1 (en) * | 1993-09-16 | 1998-11-27 | Руссель Юклаф | Method of synthesis of sulfur-containing imidazole derivatives, intermediate compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR100544105B1 (en) * | 1998-05-26 | 2006-03-24 | 삼성에스디아이 주식회사 | Nematic liquid crystal composition and liquid crystal display device using the same |
| KR100544104B1 (en) * | 1998-05-26 | 2006-03-23 | 삼성에스디아이 주식회사 | Nematic liquid crystal composition and liquid crystal display device using the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6183190A (en) * | 1984-09-29 | 1986-04-26 | Nitto Kasei Kk | 2-(4'-substituted phenyl)-5-alkyl-1,3,2-dioxaborinane, its preparation, and liquid crystal composition containing the same |
| JPS61109792A (en) * | 1984-11-01 | 1986-05-28 | Nitto Kasei Kk | 2-(4'-substituted phenyl)-5-alkyl-1,3,2-dioxanepolynan, its preparation and liquid crystal composition containing same |
| JPS61233689A (en) * | 1985-03-22 | 1986-10-17 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | Heterocyclic boron compound |
-
1986
- 1986-12-17 SU SU864162761A patent/SU1766922A1/en active
-
1987
- 1987-12-16 JP JP62316338A patent/JPS63215682A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| Авторское свидетельство СССР Me 1280318, кл, С 07 F 5/02, 1985. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2122541C1 (en) * | 1993-09-16 | 1998-11-27 | Руссель Юклаф | Method of synthesis of sulfur-containing imidazole derivatives, intermediate compounds |
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| JPS63215682A (en) | 1988-09-08 |
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