(2S,4R)-2-(2-hydroxy-3-methoxyphenyl)-4-carboxy-1,3-thiazolidine | 1262660-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2S,4R)-2-(2-hydroxy-3-methoxyphenyl)-4-carboxy-1,3-thiazolidine
• 英文别名: (2S,4R)-2-(2-hydroxy-3-methoxyphenyl)-1,3-thiazolidin-3-ium-4-carboxylate
• CAS: 1262660-61-6
• 化学式: C₁₁H₁₃NO₄S
• 分子量: 255.295
• InChiKey: UONSFKQBHNZYMD-XVKPBYJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-半胱氨酸盐酸盐无水物 、 邻香草醛 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 生成 (2S,4R)-2-(2-hydroxy-3-methoxyphenyl)-4-carboxy-1,3-thiazolidine 、 (2R,4R)-2-(2-hydroxy-3-methoxyphenyl)-4-carboxy-1,3-thiazolidine
  参考文献：
  名称：

  Conformational analysis, spectral and catalytic properties of 1,3-thiazolidines, ligands for acetophenone hydrosilylation with diphenylsilane

  摘要：

  2-Aryl- and 2-furyl-4-carboxy-1,3-thiazolidines were synthesized. Their spectral properties were studied, and conformational analysis was performed. It was shown that they exist in solution as an equilibrium of neutral and zwitter-ion forms. The influence of the nature of substitutents and of their location in a benzene ring of thiazolidines as ligands of rhodium complexes on acetophenone hydrosilylation with diphenylsilane was examined. Thiazolidines containing donor substituents in the para-position of the benzene ring were found to be the most effective; maximal asymmetrical induction (55% ee) was reached in the presence of 2-(4-methoxyphenyl)-4-carboxy-1,3-thiazolidine.

  DOI：

  10.1134/s107036321010021x

文献信息

• Conformational analysis, spectral and catalytic properties of 1,3-thiazolidines, ligands for acetophenone hydrosilylation with diphenylsilane
  作者：A. N. Skvortsov、V. M. Uvarov、D. A. de Vekki、E. P. Studentsov、N. K. Skvortsov

  DOI：10.1134/s107036321010021x

  日期：2010.10

  2-Aryl- and 2-furyl-4-carboxy-1,3-thiazolidines were synthesized. Their spectral properties were studied, and conformational analysis was performed. It was shown that they exist in solution as an equilibrium of neutral and zwitter-ion forms. The influence of the nature of substitutents and of their location in a benzene ring of thiazolidines as ligands of rhodium complexes on acetophenone hydrosilylation with diphenylsilane was examined. Thiazolidines containing donor substituents in the para-position of the benzene ring were found to be the most effective; maximal asymmetrical induction (55% ee) was reached in the presence of 2-(4-methoxyphenyl)-4-carboxy-1,3-thiazolidine.