(S)-(-)-<(4-nitrophenyl)sulfinyl>acetic acid | 125706-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(-)-<(4-nitrophenyl)sulfinyl>acetic acid
• 英文别名: 2-[(S)-(4-nitrophenyl)sulfinyl]acetic acid
• CAS: 125706-41-4
• 化学式: C₈H₇NO₅S
• 分子量: 229.213
• InChiKey: QPJSCXVOHBMWNG-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (S)-(-)-<(4-nitrophenyl)sulfinyl>acetic acid 以 氯仿 为溶剂， 反应 12.0h， 生成 (S)-(-)-Methyl <(4-nitrophenyl)sulfinyl>acetate
  参考文献：
  名称：

  Biocatalytic resolutions of sulfinylalkanoates: a facile route to optically active sulfoxides

  摘要：

  Two methods are presented for kinetic resolutions of compounds containing ester and sulfoxide functionalities (sulfinylalkanoates). In the first a crude lipase preparation from Pseudomonas sp. (K10) mediates enantioselective hydrolysis of these esters in an aqueous environment. The second method uses the same lipase preparation to promote enantioselective transesterifications with alcohols in hexane. Both procedures are suitable for preparation of sulfinylalkanoates where the ester and sulfoxide groups are separated by one or two methylene units (sulfinylacetates and sulfinylpropanoates) but compounds with three methylene "spacer groups" (sulfinylbutanoates) are not substrates for the lipase under either set of conditions.

  DOI：

  10.1021/jo00030a044
• 作为产物：
  描述：

  methyl 2-(4-nitrophenylthio)acetate 在 水 、 双氧水 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 96.0h， 生成 (S)-(-)-<(4-nitrophenyl)sulfinyl>acetic acid
  参考文献：
  名称：

  制备手性亚砜的简便方法

  摘要：

  以非常高的光学收率得到亚甲基乙酸乙酸甲酯和亚砜（R）-（1）-（6）的生物催化拆分；该产品已用于系统研究“ SPAC”反应，即不对称合成γ-羟基-α，β-不饱和酯。

  DOI：

  10.1016/s0040-4039(01)80467-6

文献信息

• A facile route to homochiral sulfoxides
  作者：Kevin Burgess、Ian Henderson

  DOI：10.1016/s0040-4039(01)80467-6

  日期：1989.1

  Biocatalytic resolutions of methyl sulfinylacetates fford sulfoxides (R)-(1) - (6) in very high optical yields; the products have been used in a systematic study of the “SPAC” reaction, an asymmetric synthesis of γ-hydroxy-α,β-unsaturated esters.

  以非常高的光学收率得到亚甲基乙酸乙酸甲酯和亚砜（R）-（1）-（6）的生物催化拆分；该产品已用于系统研究“ SPAC”反应，即不对称合成γ-羟基-α，β-不饱和酯。
• BURGESS, KEVIN;HENDERSON, IAN, TETRAHEDRON LETT., 30,(1989) N8, C. 3633-3636
  作者：BURGESS, KEVIN、HENDERSON, IAN

  DOI：——

  日期：——
• Continuous flow biocatalytic resolutions of methyl sulfinylacetates
  作者：Zhanxiang Liu、Kevin Burgess

  DOI：10.1016/j.tetlet.2011.09.024

  日期：2011.11

  Product inhibition was encountered for some substrates in the resolution of methyl sulfinylacetates mediated by lipase Amano AK, so an apparatus to continually extract the carboxylate product was devised. This was applied to resolve some sulfoxides with high enantiodifferentiation. (C) 2011 Published by Elsevier Ltd.
• Biocatalytic resolutions of sulfinylalkanoates: a facile route to optically active sulfoxides
  作者：Kevin Burgess、Ian Henderson、Kwok Kan Ho

  DOI：10.1021/jo00030a044

  日期：1992.2

  Two methods are presented for kinetic resolutions of compounds containing ester and sulfoxide functionalities (sulfinylalkanoates). In the first a crude lipase preparation from Pseudomonas sp. (K10) mediates enantioselective hydrolysis of these esters in an aqueous environment. The second method uses the same lipase preparation to promote enantioselective transesterifications with alcohols in hexane. Both procedures are suitable for preparation of sulfinylalkanoates where the ester and sulfoxide groups are separated by one or two methylene units (sulfinylacetates and sulfinylpropanoates) but compounds with three methylene "spacer groups" (sulfinylbutanoates) are not substrates for the lipase under either set of conditions.