JPH07300451A - New sulfone compound - Google Patents
New sulfone compoundInfo
- Publication number
- JPH07300451A JPH07300451A JP9084794A JP9084794A JPH07300451A JP H07300451 A JPH07300451 A JP H07300451A JP 9084794 A JP9084794 A JP 9084794A JP 9084794 A JP9084794 A JP 9084794A JP H07300451 A JPH07300451 A JP H07300451A
- Authority
- JP
- Japan
- Prior art keywords
- raw material
- sulfone compound
- compound
- hydroxyethyl
- formula
- 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.)
- Pending
Links
- -1 sulfone compound Chemical class 0.000 title claims abstract description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 239000004094 surface-active agent Substances 0.000 abstract description 3
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 abstract description 3
- KJCAMAVGYPSPSW-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanoic acid Chemical compound OCCSCCC(O)=O KJCAMAVGYPSPSW-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 239000012736 aqueous medium Substances 0.000 abstract description 2
- 229920001002 functional polymer Polymers 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 abstract description 2
- 239000002861 polymer material Substances 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 239000012528 membrane Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229940017219 methyl propionate Drugs 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、一般式（１）に示され
る新規なスルホン化合物に関するものである。FIELD OF THE INVENTION The present invention relates to a novel sulfone compound represented by the general formula (1).
【０００２】一般式（１）で示される新規なスルホン化
合物は、医薬、農薬原料、気体透過膜原料、高屈折率樹
脂原料、ポリエステル原料、機能性高分子材料、スルホ
ン基および水酸基部分が親水性、エステル部分が疎水性
を示す界面活性剤として有用な化合物である。The novel sulfone compound represented by the general formula (1) is a drug, a pesticide raw material, a gas permeable raw material, a high refractive index resin raw material, a polyester raw material, a functional polymer material, a sulfone group and a hydroxyl group portion are hydrophilic. , A compound useful as a surfactant whose ester moiety exhibits hydrophobicity.
【０００３】[0003]
【従来の技術】本発明の一般式（１）で示されるスルホ
ン化合物は、新規物質であり、これまで全く報告されて
いない。The sulfone compound represented by the general formula (1) of the present invention is a novel substance and has not been reported at all.
【０００４】[0004]
【発明が解決しようとする課題】本発明の目的は、下記
一般式（１）：The object of the present invention is to provide the following general formula (1):
【０００５】[0005]
【化２】 [Chemical 2]
【０００６】(Ｒ1、Ｒ2、Ｒ3、Ｒ4は各々独立して水
素、メチル基又はエチル基を表わし、Ｒ5は水素又は炭
素数１〜１８の炭化水素残基を表わす）に示される新規
なスルホン化合物を提供することにある。(R 1 , R 2 , R 3 and R 4 each independently represent hydrogen, a methyl group or an ethyl group, and R 5 represents hydrogen or a hydrocarbon residue having 1 to 18 carbon atoms). To provide a novel sulfone compound.
【０００７】[0007]
【課題を解決するための手段】本発明の一般式（１）で
示される新規なスルホン化合物類の製造方法を検討した
結果、例えば、３−［（２−ヒドロキシエチル）チオ］
−プロピオン酸エステル類を、水媒体中で例えば、タン
グステン酸等のような金属ポリ酸の存在下に、過酸化水
素と反応させることによって、新規な一般式（１）で示
されるスルホン化合物を高収率で製造できることを見い
だした。なお、本発明の一般式（１）で示される新規な
スルホン化合物の製造方法が上記の方法に限定されない
ことは勿論である。DISCLOSURE OF THE INVENTION As a result of examining a method for producing a novel sulfone compound represented by the general formula (1) of the present invention, for example, 3-[(2-hydroxyethyl) thio]
-Propionate esters are reacted with hydrogen peroxide in an aqueous medium in the presence of a metal polyacid such as tungstic acid or the like to enhance the sulfone compound represented by the general formula (1). It was found that it can be produced in a yield. Needless to say, the method for producing the novel sulfone compound represented by the general formula (1) of the present invention is not limited to the above method.
【０００８】[0008]
【実施例】以下、本発明を実施例を挙げて、詳細に説明
するが、本発明はこれらの実施例に限定されるものでは
ない。The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples.
【０００９】実施例１ 温度計と還流冷却管を備えた３００ｍｌの三つ口フラス
コにＨ2ＷＯ4（タングステン酸）を０．２ｇ、水６５ｍ
ｌを入れ、５０％水酸化ナトリウム水溶液を２〜３滴た
らし、Ｈ2ＷＯ4を溶解させた（この時のｐＨは約１
１）。さらに氷酢酸をｐＨが約５ぐらいになるまで滴下
した。続いて３−［（２−ヒドロキシエチル）チオ］−
プロピオン酸メチルを３２．８ｇ（０．２ｍｏｌ）入
れ、ウォーターバスにて６０℃に加熱し、３５％過酸化
水素水溶液４０ｇを滴下した。滴下終了後、室温になる
まで放冷し、亜硫酸ナトリウムを加え、過剰の過酸化水
素を分解させた。次に酢酸エチル２００ｍｌで３回抽出
した。有機層を分離、乾燥剤（硫酸マグネシウム）にて
乾燥後、乾燥剤をろ過分離し、酢酸エチルを減圧留去し
たところ白色固体３６．２ｇを得た。収率９２％。得ら
れた３−［（２−ヒドロキシエチル）スルフィニル］−
プロピオン酸メチルについて、次の物性値を得て構造を
特定した。Example 1 0.2 g of H 2 WO 4 (tungstic acid) and 65 m of water were placed in a 300 ml three-necked flask equipped with a thermometer and a reflux condenser.
1 was added, and 2-3 drops of 50% sodium hydroxide aqueous solution was added to dissolve H 2 WO 4 (pH at this time was about 1).
1). Further, glacial acetic acid was added dropwise until the pH reached about 5. Then 3-[(2-hydroxyethyl) thio]-
32.8 g (0.2 mol) of methyl propionate was added, heated to 60 ° C. in a water bath, and 40 g of 35% hydrogen peroxide aqueous solution was added dropwise. After completion of the dropping, the mixture was allowed to cool to room temperature and sodium sulfite was added to decompose excess hydrogen peroxide. It was then extracted 3 times with 200 ml of ethyl acetate. The organic layer was separated, dried with a desiccant (magnesium sulfate), the desiccant was separated by filtration, and ethyl acetate was distilled off under reduced pressure to obtain 36.2 g of a white solid. Yield 92%. Obtained 3-[(2-hydroxyethyl) sulfinyl]-
For methyl propionate, the following physical properties were obtained to identify the structure.
【００１０】 ・赤外吸収スペクトル（ＫＢｒ錠剤法、単位ｃｍ-1） （ＯＨ伸縮振動） ３５０４〜３４７３ （スルホン伸縮振動） １２７７，１１１０ （カルボニル伸縮振動） １７３４ ・1Ｈ ＮＭＲスペクトル 重ジメチルスルホキシド溶媒中ＴＭＳ基準で測定（図１
参照）[0010] ・ Infrared absorption spectrum (KBr tablet method, unit cm -1 ) (OH stretching vibration) 3504 to 3473 (sulfone stretching vibration) 1277,1110 (carbonyl stretching vibration) 1734 ・1 H NMR spectrum based on TMS in heavy dimethyl sulfoxide solvent Measurement (Fig. 1
reference)
【００１１】[0011]
【発明の効果】本発明の新規なスルホン化合物は、分子
中のスルホン基や末端官能基に基づいて、医薬、農薬原
料、界面活性剤等に有用な化合物である。INDUSTRIAL APPLICABILITY The novel sulfone compound of the present invention is a compound useful as a drug, a raw material for agricultural chemicals, a surfactant, etc., based on the sulfone group or terminal functional group in the molecule.
【図面の簡単な説明】[Brief description of drawings]
【図１】本発明の実施例１得られた物質のＴＭＳ基準に
従った重ジメチルスルホキシド溶媒における1Ｈの核磁
気共鳴スペクトル図である。FIG. 1 is a 1 H nuclear magnetic resonance spectrum diagram of the substance obtained in Example 1 of the present invention in a heavy dimethylsulfoxide solvent according to the TMS standard.
Claims (1)
はエチル基を表わし、Ｒ5は水素又は炭素数１〜１８の
炭化水素残基を表わす）に示される新規なスルホン化合
物。1. The following general formula (1): (R 1 , R 2 , R 3 and R 4 each independently represent hydrogen, a methyl group or an ethyl group, and R 5 represents hydrogen or a hydrocarbon residue having 1 to 18 carbon atoms). Sulfone compounds.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9084794A JPH07300451A (en) | 1994-03-11 | 1994-04-28 | New sulfone compound |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6-40780 | 1994-03-11 | ||
| JP4078094 | 1994-03-11 | ||
| JP9084794A JPH07300451A (en) | 1994-03-11 | 1994-04-28 | New sulfone compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07300451A true JPH07300451A (en) | 1995-11-14 |
Family
ID=26380297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9084794A Pending JPH07300451A (en) | 1994-03-11 | 1994-04-28 | New sulfone compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07300451A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009108028A (en) * | 2007-08-30 | 2009-05-21 | National Sun Yat-Sen Univ | Sulfur-containing compounds, their preparation and pharmaceutical use |
-
1994
- 1994-04-28 JP JP9084794A patent/JPH07300451A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009108028A (en) * | 2007-08-30 | 2009-05-21 | National Sun Yat-Sen Univ | Sulfur-containing compounds, their preparation and pharmaceutical use |
| US8399661B2 (en) | 2007-08-30 | 2013-03-19 | National Sun Yat-Sen University | Sulfur-containing compound, method of preparation and pharmaceutical uses thereof |
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