methyl (S)-2-phenylsulfinylacetate | 122331-46-8

• 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: methyl (S)-2-phenylsulfinylacetate
• 英文别名: methyl 2-[(S)-phenylsulfinyl]acetate
• CAS: 122331-46-8
• 化学式: C₉H₁₀O₃S
• 分子量: 198.243
• InChiKey: JPPXZUDQIXZLIL-ZDUSSCGKSA-N

物化性质

• 沸点：
  341.2±0.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯硫基乙酸 在 phosphate buffer 、 Nocardia diaphanozonaria JCM 3208 whole cells 作用下， 以 水 为溶剂， 反应 24.0h， 生成 methyl (S)-2-phenylsulfinylacetate
  参考文献：
  名称：

  Microbial deracemization of α-substituted carboxylic acids: control of the reaction path

  摘要：

  A novel approach to preparing optically active alpha-substituted carboxylic acids using the whole cells of Nocardia diaphanozonaria JCM 3208 is described. When 2-phenylthiopropanoic acid and 2-methyl-3-phenylpropanoic acid were subjected to the reaction under aerobic conditions, the oxidation reaction proceeded preferentially rather than deracemization of these substrates. Herein, we report the design of reaction conditions to increase the deracemization activity in preference to oxidation reactions. In addition, we have successfully detected a metabolic intermediate in the reaction mixture of 2-methyl-3-plienylpropanoic acid, which indicates that the deracemization is a competitive reaction against the beta-oxidation pathway of fatty acid metabolism. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.049

文献信息

• Chemistry of oxaziridines. 17. N-(Phenylsulfonyl)(3,3-dichlorocamphoryl)oxaziridine: a highly efficient reagent for the asymmetric oxidation of sulfides to sulfoxides
  作者：Franklin A. Davis、R. Thimma Reddy、Wei Han、Patrick J. Carroll

  DOI：10.1021/ja00030a045

  日期：1992.2

  The synthesis, structure, and enantioselective oxidations of a new chiral N-sulfonyloxaziridine 12c [3,3-dichloro- 1,7,7-trimethyl-2'-(phenylsulfonyl)spiro[bicyclo[2.2.1]heptane-2,3'-oxaziridine]] are reported. This oxidant, which exhibits remarkably high and predictable ee's for the enantioselective oxidation of prochiral sulfides to sulfoxides, is prepared in three steps from (+)- or (-)-camphor

  一种新型手性 N-磺酰氧氮丙啶 12c [3,3-二氯-1,7,7-三甲基-2'-(苯基磺酰基)螺[双环[2.2.1]庚烷-2,3]的合成、结构和对映选择性氧化'-oxaziridine]] 报道。这种氧化剂在将前手性硫化物对映选择性氧化成亚砜方面表现出非常高且可预测的 ee，它是由 (+)- 或 (-)-樟脑以 50% 的总产率通过三个步骤制备的
• Enzymatic Resolution and Decarboxylative Functionalization of α‐Sulfinyl Esters
  作者：Suraksha Gahalawat、Yesu Addepalli、Stephen P. Fink、Lakshmi Kasturi、Sanford D. Markowitz、Joseph M. Ready

  DOI：10.1002/chem.202302996

  日期：2024.2

  Enzymatic resolution of α-sulfinyl esters gives recovered ester and α-sulfinyl acid in high enantiomeric purity. Decarboxylative functionalization provides access to a wide range of optically active sulfoxides in both enantiomeric forms.

  α-亚爷酯的酶促分离得到具有高对映体纯度的回收酯和 α-亚爷酸。脱羧官能团化提供了两种对映体形式的多种光学活性亚砜。
• (-)-.alpha.,.alpha.-Dichlorocamphorsulfonyloxaziridine: a superior reagent for the asymmetric oxidation of sulfides to sulfoxides
  作者：Franklin A. Davis、R. ThimmaReddy、Michael C. Weismiller

  DOI：10.1021/ja00197a080

  日期：1989.7