S-ethyl 2-phenylsulfanylpropanethioate | 170879-58-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: S-ethyl 2-phenylsulfanylpropanethioate
• CAS: 170879-58-0
• 化学式: C₁₁H₁₄OS₂
• 分子量: 226.364
• InChiKey: FVWXDYXWJFPUNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  S-ethyl 2-phenylsulfanylpropanethioate 在 sodium hydroxide 、 三辛胺 、 PIPES buffer 作用下， 以 甲苯 为溶剂， 反应 65.0h， 生成 (R)-2-(phenylthio)propanoic acid
  参考文献：
  名称：

  Enzymatic Resolution Coupled with Substrate Racemization Using a Thioester Substrate

  摘要：

  DOI：

  10.1021/ja00140a037
• 作为产物：
  描述：

  2-phenylsulfanyl-propionic acid 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 S-ethyl 2-phenylsulfanylpropanethioate
  参考文献：
  名称：

  Dynamic Enzymatic Resolution of Thioesters

  摘要：

  A detailed investigation of several issues related to the enzymatic resolution of thioesters under conditions of continuous racemization of substrate was conducted. The kinetic acidity of the alpha-protons of a series of alpha-substituted propionate thioesters was studied. It was found that the rate of alpha-proton exchange could be enhanced as much as 20-fold by variation of the thiol moiety, increasing the range of compounds to which enzymatic dynamic resolution may be applied. The relative rates of hydrolysis of ethyl butyrate and ethyl thiobutyrate by several enzymes commonly used in enzymatic resolution were determined. All of the enzymes studied exhibited similar rates of thioester and oxoester hydrolysis except for the esterase from pig liver, which showed very low activity in thioester hydrolysis. Dynamic resolution of the propargyl and trifluoroethyl thioesters of alpha-phenylpropionate was conducted using subtilisin Carlsberg as a catalyst. These examples demonstrated that enzymatic dynamic resolution can be applied even when the rate of alpha-proton exchange and the enantioselectivity of the enzyme are fairly low. A dynamic enzymatic transesterification procedure was demonstrated in the resolution of the trifluoroethyl thioester of alpha-(2,4-dichlorophenoxy)propionate, and product was obtained in 93% ee. This work helps expand and define the scope of enzymatic dynamic resolution of thioesters.

  DOI：

  10.1021/ja980445b