(E)-4-oxo-4-pyrrolidin-1-yl-but-2-enoic acid methyl ester | 138004-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (E)-4-oxo-4-pyrrolidin-1-yl-but-2-enoic acid methyl ester
• 英文别名: methyl (E)-4-oxo-4-pyrrolidin-1-ylbut-2-enoate
• CAS: 138004-87-2
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: DMJYELWOYXZEFI-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-oxo-4-pyrrolidin-1-yl-but-2-enoic acid methyl ester 950.0~1000.0 ℃ 、0.2 Pa 条件下， 生成 endo-(5S)-4-methoxycarbonyl-1-azabicyclo<3.3.0>octan-2-one 、 exo-(5S)-4-methoxycarbonyl-1-azabicyclo<3.3.0>octan-2-one
  参考文献：
  名称：

  Cyclisation at very high temperature. Thermal transformations of N-alkyl and N, N-dialkyl amides of α,β-unsaturated acids into mono- and bicyclic heterocycles under FVT conditions

  摘要：

  Cyclisations of N-alkyl and N,N-dialkyl cinnamic amides to the corresponding pyrrolidin-2-ones under the conditions of flash vacuum thermolysis (FVT), are described. It was found that these reactions proceed at 950-1000 degrees C affording in various yields the mixtures of isomeric mono and bicyclic gamma-lactams, which were separated chromatographically and analysed by means of NMR spectroscopy. Two alternative mechanisms for the title process are proposed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.011
• 作为产物：
  描述：

  四氢吡咯 、 methyl (E)-4-chloro-4-oxo-2-butenoate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以33%的产率得到(E)-4-oxo-4-pyrrolidin-1-yl-but-2-enoic acid methyl ester
  参考文献：
  名称：

  Cyclisation at very high temperature. Thermal transformations of N-alkyl and N, N-dialkyl amides of α,β-unsaturated acids into mono- and bicyclic heterocycles under FVT conditions

  摘要：

  Cyclisations of N-alkyl and N,N-dialkyl cinnamic amides to the corresponding pyrrolidin-2-ones under the conditions of flash vacuum thermolysis (FVT), are described. It was found that these reactions proceed at 950-1000 degrees C affording in various yields the mixtures of isomeric mono and bicyclic gamma-lactams, which were separated chromatographically and analysed by means of NMR spectroscopy. Two alternative mechanisms for the title process are proposed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.011