Methyl 2,3-diacetyloxy-2-(methoxycarbonylamino)propanoate | 182223-75-2

• 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: Methyl 2,3-diacetyloxy-2-(methoxycarbonylamino)propanoate
• CAS: 182223-75-2
• 化学式: C₁₀H₁₅NO₈
• 分子量: 277.231
• InChiKey: OTBRKDHFCARACR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 2,3-diacetyloxy-2-(methoxycarbonylamino)propanoate 在 甲醇 、 potassium carbonate 作用下， 反应 1.5h， 以78%的产率得到4-methoxycarbonyl-4-oxazolin-2-one
  参考文献：
  名称：

  Oxidation of didehydro-α-amino acids as a route to β-hydroxy-or β-amino-pyruvic derivatives and to α-acylglycinates

  摘要：

  Oxidation of protected didehydro-alpha-amino acids with N-bromosuccinimide or lead tetraacetate affords imines of beta-bromo- or beta-acetoxy-pyruvates. The hydrolysis of brominated imines proceeds through addition of water followed by intramolecular displacement of bromine, According to experimental procedures, intermediate hydroxyaziridines, hydroxyoxazolines or aminoepoxides have to be considered. Two pathways are examined for hydrolysis of beta-acetoxyimines: cyclisation to oxazolones or conversion to acylglycinates when imines are converted to the isomeric enamines prior to deprotection.

  DOI：

  10.1039/p19960001833
• 作为产物：
  描述：

  lead(IV) tetraacetate 、 2-<(methoxycarbonyl)amino>-2-propenoic acid methyl ester 以 二氯甲烷 为溶剂， 反应 48.0h， 以70%的产率得到Methyl 2,3-diacetyloxy-2-(methoxycarbonylamino)propanoate
  参考文献：
  名称：

  Oxidation of didehydro-α-amino acids as a route to β-hydroxy-or β-amino-pyruvic derivatives and to α-acylglycinates

  摘要：

  Oxidation of protected didehydro-alpha-amino acids with N-bromosuccinimide or lead tetraacetate affords imines of beta-bromo- or beta-acetoxy-pyruvates. The hydrolysis of brominated imines proceeds through addition of water followed by intramolecular displacement of bromine, According to experimental procedures, intermediate hydroxyaziridines, hydroxyoxazolines or aminoepoxides have to be considered. Two pathways are examined for hydrolysis of beta-acetoxyimines: cyclisation to oxazolones or conversion to acylglycinates when imines are converted to the isomeric enamines prior to deprotection.

  DOI：

  10.1039/p19960001833

文献信息

• Oxidation of didehydro-α-amino acids as a route to β-hydroxy-or β-amino-pyruvic derivatives and to α-acylglycinates
  作者：Benoît Miossec、Hélène Rudyk、Loïc Toupet、Renée Danion-Bougot、Daniel Danion

  DOI：10.1039/p19960001833

  日期：——

  Oxidation of protected didehydro-alpha-amino acids with N-bromosuccinimide or lead tetraacetate affords imines of beta-bromo- or beta-acetoxy-pyruvates. The hydrolysis of brominated imines proceeds through addition of water followed by intramolecular displacement of bromine, According to experimental procedures, intermediate hydroxyaziridines, hydroxyoxazolines or aminoepoxides have to be considered. Two pathways are examined for hydrolysis of beta-acetoxyimines: cyclisation to oxazolones or conversion to acylglycinates when imines are converted to the isomeric enamines prior to deprotection.