(4S)-3-((2E)-butenoyl)-4-phenylthiazolidine-2-thione | 1383790-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-3-((2E)-butenoyl)-4-phenylthiazolidine-2-thione
• 英文别名: N-crotonyl-4-phenylthiazolidinethione；(E)-1-[(4S)-4-phenyl-2-sulfanylidene-1,3-thiazolidin-3-yl]but-2-en-1-one
• CAS: 1383790-21-3
• 化学式: C₁₃H₁₃NOS₂
• 分子量: 263.384
• InChiKey: BGCYWJLUYJEAFU-SZHMKSFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-3-((2E)-butenoyl)-4-phenylthiazolidine-2-thione 、 S-4-苯基噻唑啉-2-硫酮 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  Stereochemical control on the Michael addition of chiral 1,3-oxazolidine-2-thiones to N-crotonyl 1,3-oxazolidin-2-ones

  摘要：

  Addition of both antipodes of 4-phenyl 1,3-oxazolidine-2-thione to 4-substituted N-crotonyl 1,3-oxazolidin-2-ones furnished Michael addition products. A perfect match occurred when both Michael donor and acceptor possessed the same stereochemistry and a mismatch when they had opposite stereochemistries. The newly created stereochemical center was shown to be governed by the Michael donor and not by the acceptor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.074
• 作为产物：
  描述：

  2-丁烯酰氯 、 S-4-苯基噻唑啉-2-硫酮 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (4S)-3-((2E)-butenoyl)-4-phenylthiazolidine-2-thione
  参考文献：
  名称：

  Oxazolidine-2-thiones and Thiazolidine-2-thiones as Nucleophiles in Intermolecular Michael Additions

  摘要：

  Conjugate addition of thiazolidinethiones and oxazolidinethiones to N-crotonylthiazolidinethiones and -oxazolidinethiones was observed in the presence of excess triethylamine in dichloromethane. The addition takes place by the nitrogen of the heterocycle with high diastereoselectivity. It was observed that the stereoselective addition occurs on the anti-s-cis conformation of the N-enoyl sulfur-containing heterocycle.

  DOI：

  10.1021/ol301489y

文献信息

• Oxazolidine-2-thiones and Thiazolidine-2-thiones as Nucleophiles in Intermolecular Michael Additions
  作者：Laura Munive、Veronica M. Rivas、Aurelio Ortiz、Horacio F. Olivo

  DOI：10.1021/ol301489y

  日期：2012.7.6

  Conjugate addition of thiazolidinethiones and oxazolidinethiones to N-crotonylthiazolidinethiones and -oxazolidinethiones was observed in the presence of excess triethylamine in dichloromethane. The addition takes place by the nitrogen of the heterocycle with high diastereoselectivity. It was observed that the stereoselective addition occurs on the anti-s-cis conformation of the N-enoyl sulfur-containing heterocycle.
• Stereochemical control on the Michael addition of chiral 1,3-oxazolidine-2-thiones to N-crotonyl 1,3-oxazolidin-2-ones
  作者：Laura Munive、Sena A. Dzakuma、Horacio F. Olivo

  DOI：10.1016/j.tetlet.2012.12.074

  日期：2013.3

  Addition of both antipodes of 4-phenyl 1,3-oxazolidine-2-thione to 4-substituted N-crotonyl 1,3-oxazolidin-2-ones furnished Michael addition products. A perfect match occurred when both Michael donor and acceptor possessed the same stereochemistry and a mismatch when they had opposite stereochemistries. The newly created stereochemical center was shown to be governed by the Michael donor and not by the acceptor. (C) 2012 Elsevier Ltd. All rights reserved.