S-phenyl 2-phenylpropanethioate | 100683-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-phenyl 2-phenylpropanethioate
• 英文别名: S-phenyl 2-phenylpropylthioester；phenylthio 2-phenylpropanoate
• CAS: 100683-61-2
• 化学式: C₁₅H₁₄OS
• 分子量: 242.342
• InChiKey: LWHVKOKQTSVHAM-UHFFFAOYSA-N

物化性质

• 沸点：
  365.8±21.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  S-phenyl 2-phenylpropanethioate 在 氘代甲醇 、 三乙胺 作用下， 以 氘代甲苯 为溶剂， 生成
  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
• 作为产物：
  描述：

  在 臭氧 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 S-phenyl 2-phenylpropanethioate
  参考文献：
  名称：

  Preparation of .alpha.-substituted S-phenyl thio esters from aldehydes and (phenylthio)nitromethane

  摘要：

  DOI：

  10.1021/jo00357a012

文献信息

• Regioselective Thiocarbonylation of Vinyl Arenes
  作者：Vera Hirschbeck、Paul H. Gehrtz、Ivana Fleischer

  DOI：10.1021/jacs.6b11020

  日期：2016.12.28

  A palladium-catalyzed thiocarbonylation of styrene derivatives is reported for the first time. The combination of thiols as nucleophiles and a bidentate ligand ensures a unique reaction outcome with high regioselectivity toward the more valuable branched isomer and new reactivity. The ambient reaction conditions (temperature, catalyst loading) and the use of a CO surrogate render this transformation

  首次报道了钯催化的苯乙烯衍生物的硫代羰基化。作为亲核试剂的硫醇和双齿配体的组合确保了独特的反应结果，对更有价值的支链异构体和新的反应性具有高区域选择性。环境反应条件（温度、催化剂负载）和 CO 替代物的使用使这种转化成为从可用原料合成硫酯的有用方法。该系统可以容忍芳烃和硫醇取代基上的各种官能团。值得注意的是，具有挑战性的邻位取代苯乙烯以前所未有的高区域选择性转化。
• Regiodivergent Carbonylation of Alkenes: Selective Palladium‐Catalyzed Synthesis of Linear and Branched Selenoesters
  作者：Zhusong Cao、Qiang Wang、Helfried Neumann、Matthias Beller

  DOI：10.1002/anie.202313714

  日期：2024.1.8

  The first regioselective selenocarbonylation of alkenes is reported. This general protocol provides a variety of branched and linear selenoesters with wide functional group compatibility and tunable regioselectivity.

  首次报道了烯烃的区域选择性硒代羰基化反应。该通用方案提供了各种支链和线性硒酯，具有广泛的官能团兼容性和可调的区域选择性。
• Palladium-Catalyzed Thiocarbonylation of Alkenes toward Linear Thioesters
  作者：Han-Jun Ai、Fengqian Zhao、Hui-Qing Geng、Xiao-Feng Wu

  DOI：10.1021/acscatal.1c00414

  日期：2021.3.19
• Resolution of pentafluorophenyl 2-phenylpropanoate using combinations of quasi-enantiomeric oxazolidin-2-ones
  作者：Najla Al Shaye、David M. Benoit、Sameer Chavda、Elliot Coulbeck、Marco Dingjan、Jason Eames、Yonas Yohannes

  DOI：10.1016/j.tetasy.2011.02.022

  日期：2011.2

  The kinetic, mutual and parallel resolution of a series of structurally related active esters derived from 2-phenylpropanoic acid using a combination of quasi-enantiomeric oxazolidin-2-ones is discussed. (C) 2011 Elsevier Ltd. All rights reserved.
• BARRETT, A. G. M.;GRABOSKI, G. G.;RUSSELL, M. A., J. ORG. CHEM., 1986, 51, N 7, 1012-1015
  作者：BARRETT, A. G. M.、GRABOSKI, G. G.、RUSSELL, M. A.

  DOI：——

  日期：——