2-(2-Phenyl-5-methyl-4-oxothiazolidin-3-yl)acetic acid methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2-Phenyl-5-methyl-4-oxothiazolidin-3-yl)acetic acid methyl ester
• 英文别名: Methyl 2-(5-methyl-4-oxo-2-phenyl-1,3-thiazolidin-3-yl)acetate
• 化学式: C₁₃H₁₅NO₃S
• 分子量: 265.333
• InChiKey: DHKIFNFIAIRJIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-Phenyl-5-methyl-4-oxothiazolidin-3-yl)acetic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以97%的产率得到2-(2-Phenyl-5-methyl-4-oxothiazolidin-3-yl)acetic acid
  参考文献：
  名称：

  Strategies for Combinatorial Organic Synthesis: Solution and Polymer-Supported Synthesis of 4-Thiazolidinones and 4-Metathiazanones Derived from Amino Acids

  摘要：

  Both the solution and polymer-supported synthesis of 4-thiazolidinones and 4-metathiazanones derived from amino acids are described. Solution studies showed that moderate to high yields of 4-thiazolidinones could be obtained from the one-pot, three-component condensation of amino acid esters (glycine, alanine, beta-alanine, phenylalanine, and valine), an aldehyde (benzaldehyde, o-tolualdehyde, m-tolualdehyde, p-tolualdehyde, and 3-pyridinecarboxaldehyde), and an alpha-mercapto carboxylic acid (thiolactic and mercaptoacetic acid). Acylation of standard peptide synthesis resins with an Fmoc-protected amino acid, followed by deprotection of the Fmoc group and condensation with aldehydes and an alpha-mercapto or beta-mercapto carboxylic acid, lead to the formation of the five- and six-membered heterocycles. The stepwise assembly of 4-thiazolidinones by treatment of the intermediate imine with an alpha-mercapto carboxylic acid was also demonstrated. Cleavage from the support under acidic (trifluoroacetic acid) conditions gave high yields and high purities of the liberated 4-thiazolidinones and lower yields of 4-metathiazanones.

  DOI：

  10.1021/jo00127a044
• 作为产物：
  描述：

  甘氨酸甲酯盐酸盐 、 苯甲醛 、 硫代乳酸 在 N,N-二异丙基乙胺 作用下， 以 苯 为溶剂， 反应 18.0h， 以92%的产率得到2-(2-Phenyl-5-methyl-4-oxothiazolidin-3-yl)acetic acid methyl ester
  参考文献：
  名称：

  Strategies for Combinatorial Organic Synthesis: Solution and Polymer-Supported Synthesis of 4-Thiazolidinones and 4-Metathiazanones Derived from Amino Acids

  摘要：

  Both the solution and polymer-supported synthesis of 4-thiazolidinones and 4-metathiazanones derived from amino acids are described. Solution studies showed that moderate to high yields of 4-thiazolidinones could be obtained from the one-pot, three-component condensation of amino acid esters (glycine, alanine, beta-alanine, phenylalanine, and valine), an aldehyde (benzaldehyde, o-tolualdehyde, m-tolualdehyde, p-tolualdehyde, and 3-pyridinecarboxaldehyde), and an alpha-mercapto carboxylic acid (thiolactic and mercaptoacetic acid). Acylation of standard peptide synthesis resins with an Fmoc-protected amino acid, followed by deprotection of the Fmoc group and condensation with aldehydes and an alpha-mercapto or beta-mercapto carboxylic acid, lead to the formation of the five- and six-membered heterocycles. The stepwise assembly of 4-thiazolidinones by treatment of the intermediate imine with an alpha-mercapto carboxylic acid was also demonstrated. Cleavage from the support under acidic (trifluoroacetic acid) conditions gave high yields and high purities of the liberated 4-thiazolidinones and lower yields of 4-metathiazanones.

  DOI：

  10.1021/jo00127a044

文献信息

• Strategies for Combinatorial Organic Synthesis: Solution and Polymer-Supported Synthesis of 4-Thiazolidinones and 4-Metathiazanones Derived from Amino Acids
  作者：Christopher P. Holmes、Jason P. Chinn、Gary C. Look、Eric M. Gordon、Mark A. Gallop

  DOI：10.1021/jo00127a044

  日期：1995.11

  Both the solution and polymer-supported synthesis of 4-thiazolidinones and 4-metathiazanones derived from amino acids are described. Solution studies showed that moderate to high yields of 4-thiazolidinones could be obtained from the one-pot, three-component condensation of amino acid esters (glycine, alanine, beta-alanine, phenylalanine, and valine), an aldehyde (benzaldehyde, o-tolualdehyde, m-tolualdehyde, p-tolualdehyde, and 3-pyridinecarboxaldehyde), and an alpha-mercapto carboxylic acid (thiolactic and mercaptoacetic acid). Acylation of standard peptide synthesis resins with an Fmoc-protected amino acid, followed by deprotection of the Fmoc group and condensation with aldehydes and an alpha-mercapto or beta-mercapto carboxylic acid, lead to the formation of the five- and six-membered heterocycles. The stepwise assembly of 4-thiazolidinones by treatment of the intermediate imine with an alpha-mercapto carboxylic acid was also demonstrated. Cleavage from the support under acidic (trifluoroacetic acid) conditions gave high yields and high purities of the liberated 4-thiazolidinones and lower yields of 4-metathiazanones.