甲基丙二酸甲酯N-乙氧基酰胺 | 151599-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基丙二酸甲酯N-乙氧基酰胺
• 英文名称: methylmalonic acid methyl ester N-ethoxyamide
• 英文别名: Methyl 3-(ethoxyamino)-2-methyl-3-oxopropanoate
• CAS: 151599-48-3
• 化学式: C₇H₁₃NO₄
• 分子量: 175.185
• InChiKey: PISAYRMKJLYNGP-UHFFFAOYSA-N

物化性质

• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基丙二酸甲酯N-乙氧基酰胺 在 五氯化磷 、 溴 、 碘 、 magnesium 作用下， 以 苯 为溶剂， 反应 17.0h， 生成 2-氰基丙酸甲酯
  参考文献：
  名称：

  Ketenimine-nitrile rearrangements of N-alkoxyketenimines under their generation conditions

  摘要：

  C,C-Substituted N-ethoxyketenimines are extremely unstable even under their generation conditions (dehydrochlorination of N-ethoxyimidoyl chlorides, dehalogenation of alpha-bromo-N-ethoxyimidoyl halides, the reaction of methylmethoxycarbonylketene with N-ethoxytriphenylphosphinimine) undergo two types of rearrangements: synchronous ring decomposition down to acetaldehyde and the corresponding CH-nitrile and 1,3-migration of the EtO group with formation of alpha-ethoxynitriles. We suggest that the instability of N-alkoxyketenimines is mainly due to weakening of the NO bond as a result of pi(CC)-sigma(NO)* hyperconjugation.

  DOI：

  10.1007/bf00863370
• 作为产物：
  描述：

  3-氯-2-甲基-3-氧代丙酸甲酯 、 O-乙基羟胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以80.5%的产率得到甲基丙二酸甲酯N-乙氧基酰胺
  参考文献：
  名称：

  Ketenimine-nitrile rearrangements of N-alkoxyketenimines under their generation conditions

  摘要：

  C,C-Substituted N-ethoxyketenimines are extremely unstable even under their generation conditions (dehydrochlorination of N-ethoxyimidoyl chlorides, dehalogenation of alpha-bromo-N-ethoxyimidoyl halides, the reaction of methylmethoxycarbonylketene with N-ethoxytriphenylphosphinimine) undergo two types of rearrangements: synchronous ring decomposition down to acetaldehyde and the corresponding CH-nitrile and 1,3-migration of the EtO group with formation of alpha-ethoxynitriles. We suggest that the instability of N-alkoxyketenimines is mainly due to weakening of the NO bond as a result of pi(CC)-sigma(NO)* hyperconjugation.

  DOI：

  10.1007/bf00863370

文献信息

• Ketenimine-nitrile rearrangements of N-alkoxyketenimines under their generation conditions
  作者：G. V. Shustov、A. V. Kachanov、R. G. Kostyanovskii

  DOI：10.1007/bf00863370

  日期：1992.11

  C,C-Substituted N-ethoxyketenimines are extremely unstable even under their generation conditions (dehydrochlorination of N-ethoxyimidoyl chlorides, dehalogenation of alpha-bromo-N-ethoxyimidoyl halides, the reaction of methylmethoxycarbonylketene with N-ethoxytriphenylphosphinimine) undergo two types of rearrangements: synchronous ring decomposition down to acetaldehyde and the corresponding CH-nitrile and 1,3-migration of the EtO group with formation of alpha-ethoxynitriles. We suggest that the instability of N-alkoxyketenimines is mainly due to weakening of the NO bond as a result of pi(CC)-sigma(NO)* hyperconjugation.