ethyl alpha-(benzylmercapto)-propionate | 52414-72-9

• 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: ethyl alpha-(benzylmercapto)-propionate
• 英文别名: Ethyl 2-(benzylsulfanyl)propanoate；ethyl 2-benzylsulfanylpropanoate
• CAS: 52414-72-9
• 化学式: C₁₂H₁₆O₂S
• 分子量: 224.324
• InChiKey: KIQWCXXXGXNNGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-苄烯丁胺 、 ethyl alpha-(benzylmercapto)-propionate 在 tin(II) trifluoromethanesulfonate 、 N,N-二异丙基乙胺 作用下， 生成 1-Benzyl-3-benzylsulfanyl-3-methyl-4-phenyl-azetidin-2-one
  参考文献：
  名称：

  从新型亚锡烯醇化物和亚胺合成 β-内酰胺

  摘要：

  由含硫α-取代基的氧酯，通过使用三氟甲磺酸亚锡制备相应的烯醇亚锡。烯醇化物与各种亚胺反应以提供β-内酰胺。

  DOI：

  10.1246/cl.1989.1331
• 作为产物：
  描述：

  2-（苄硫基）丙酸| 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 ethyl alpha-(benzylmercapto)-propionate
  参考文献：
  名称：

  Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates

  摘要：

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.009

文献信息

• A New Method for Stereocontrolled Synthesis of Substituted Tetrahydrothiophenes
  作者：Andrés Molina Ponce、Larry E. Overman

  DOI：10.1021/ja001975m

  日期：2000.9.1

  A variety of substituted 3-acyltetrahydrothiophenes can be prepared with high stereoselectivity in 50−70% yield by acid-promoted condensation of mercapto allylic alcohols 1 (X = S) with aldehydes and ketones. The mercapto allylic alcohol must be substituted at the internal alkene carbon and the terminal alkene carbon must be unsubstituted. This new synthesis of tetrahydrothiophenes will be most useful

  通过巯基烯丙醇 1 (X = S) 与醛和酮的酸促进缩合，可以以 50-70% 的收率以高立体选择性制备各种取代的 3-酰基四氢噻吩。巯基烯丙醇的内部烯烃碳必须被取代，末端烯烃碳必须未被取代。这种四氢噻吩的新合成对于制备在 C2 和 C5 处具有顺式侧链的 3-酰基四氢噻吩最有用。在 (4R)-9 到四氢噻吩 22 的转化过程中对映体纯度的完全保持与环化-频哪醇途径一致（24 → 25 → 26 → 27，方案 8）。
• SUGANO, YUICHI;NARUTO, SHUNJI, CHEM. LETT.,(1989) N, C. 1331-1334
  作者：SUGANO, YUICHI、NARUTO, SHUNJI

  DOI：——

  日期：——
• US3946071A
  申请人：——

  公开号：US3946071A

  公开（公告）日：1976-03-23
• Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates
  作者：Surrinder Koul、Jawahir Lal Koul、Budh Singh、Munish Kapoor、Rajinder Parshad、Kuldeep S. Manhas、Subhash C. Taneja、Ghulam N. Qazi

  DOI：10.1016/j.tetasy.2005.07.009

  日期：2005.8

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of β-Lactams from Novel Stannous Enolates and Imines
  作者：Yuichi Sugano、Shunji Naruto

  DOI：10.1246/cl.1989.1331

  日期：1989.8

  From the oxygen esters containing sulfur α-substituent, corresponding stannous enolates were prepared by the use of stannous trifluoromethanesulfonate. The enolates reacted with various imines to provide β-lactams.

  由含硫α-取代基的氧酯，通过使用三氟甲磺酸亚锡制备相应的烯醇亚锡。烯醇化物与各种亚胺反应以提供β-内酰胺。