2-((R)-3-Carboxy-1-methyl-propyl)-oxazole-4-carboxylic acid methyl ester | 153180-37-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-((R)-3-Carboxy-1-methyl-propyl)-oxazole-4-carboxylic acid methyl ester
• CAS: 153180-37-1
• 化学式: C₁₀H₁₃NO₅
• 分子量: 227.217
• InChiKey: PIUOFUQJACDYJE-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-((R)-3-Carboxy-1-methyl-propyl)-oxazole-4-carboxylic acid methyl ester 、 叔丁醇 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 反应 14.0h， 以47%的产率得到Methyl2-<3-<(tert-butoxycarbonyl)amino>-1(R)-methylpropyl>oxazole-4-carboxylate
  参考文献：
  名称：

  Dimethyl amino[(phenylthio)methyl]malonate: a useful C-3 unit in a mild, direct synthesis of oxazole-4-carboxylates

  摘要：

  N-Acyl derivatives of the title compound undergo oxidative cyclization upon treatment with N-chlorosuccinimide in DMF to form dimethyl 4,5-dihydro(phenylthio)oxazole-4,4-dicarboxylates 4 which then are decarbomethoxylated with concomitant loss of thiophenoxide to form 2-substituted-4-carbomethoxy-5-unsubstituted oxazoles 1. The mildness and generality of this method has been demonstrated by the synthesis of a variety of examples, including a fragment used for a synthesis of calyculin A.

  DOI：

  10.1021/jo00073a040
• 作为产物：
  描述：

  Methyl 2-<3-(tert-butoxycarbonyl)-1(R)-methylpropyl>oxazole-4-carboxylate 在 三氟乙酸 作用下， 反应 16.0h， 以88%的产率得到2-((R)-3-Carboxy-1-methyl-propyl)-oxazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Dimethyl amino[(phenylthio)methyl]malonate: a useful C-3 unit in a mild, direct synthesis of oxazole-4-carboxylates

  摘要：

  N-Acyl derivatives of the title compound undergo oxidative cyclization upon treatment with N-chlorosuccinimide in DMF to form dimethyl 4,5-dihydro(phenylthio)oxazole-4,4-dicarboxylates 4 which then are decarbomethoxylated with concomitant loss of thiophenoxide to form 2-substituted-4-carbomethoxy-5-unsubstituted oxazoles 1. The mildness and generality of this method has been demonstrated by the synthesis of a variety of examples, including a fragment used for a synthesis of calyculin A.

  DOI：

  10.1021/jo00073a040