Methyl 2-oxo-5-phenyl-1,3-dihydropyrrole-4-carboxylate | 1026234-38-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Methyl 2-oxo-5-phenyl-1,3-dihydropyrrole-4-carboxylate
• CAS: 1026234-38-7
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: RXOIYSNECNYFLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2-oxo-5-phenyl-1,3-dihydropyrrole-4-carboxylate 在 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 14.0h， 生成 methyl (4Z)-4-benzylidene-1-methyl-5-oxo-2-phenylpyrrole-3-carboxylate
  参考文献：
  名称：

  Interesting phototransformations of aziridinylmaleates and -fumarates. Steady-state and laser flash photolysis studies

  摘要：

  The phototransformations of some disubstituted aziridylmaleates 3a-d and -fumarates 4a-c have been studied by steady-state photolysis, product analysis, and by laser flash photolysis. The formation of the different pyrrolidone derivatives in these reactions could be understood in terms of azomethine ylide intermediates 5a-d, which undergo facile 1,2-rearrangements leading to Schiff bases and their subsequent cyclization, followed by further transformations. Laser flash photolysis studies substantiate the formation of azomethine ylide intermediates from these substrates under direct irradiation; however, they are not formed under triplet sensitization by aromatic ketones. Geometric isomerization of the ethylenic diester moiety takes place both under direct and sensitized irradiations.

  DOI：

  10.1021/jo00048a045
• 作为产物：
  描述：

  cis-2,3-diphenylaziridine 以 苯 为溶剂， 反应 22.0h， 生成 Methyl 2-oxo-5-phenyl-1,3-dihydropyrrole-4-carboxylate
  参考文献：
  名称：

  Interesting phototransformations of aziridinylmaleates and -fumarates. Steady-state and laser flash photolysis studies

  摘要：

  The phototransformations of some disubstituted aziridylmaleates 3a-d and -fumarates 4a-c have been studied by steady-state photolysis, product analysis, and by laser flash photolysis. The formation of the different pyrrolidone derivatives in these reactions could be understood in terms of azomethine ylide intermediates 5a-d, which undergo facile 1,2-rearrangements leading to Schiff bases and their subsequent cyclization, followed by further transformations. Laser flash photolysis studies substantiate the formation of azomethine ylide intermediates from these substrates under direct irradiation; however, they are not formed under triplet sensitization by aromatic ketones. Geometric isomerization of the ethylenic diester moiety takes place both under direct and sensitized irradiations.

  DOI：

  10.1021/jo00048a045

文献信息

• Interesting phototransformations of aziridinylmaleates and -fumarates. Steady-state and laser flash photolysis studies
  作者：D. Ramaiah、K. Ashok、R. Barik、D. Venugopal、N. P. Rath、K. Bhattacharyya、P. K. Das、M. V. George

  DOI：10.1021/jo00048a045

  日期：1992.10

  The phototransformations of some disubstituted aziridylmaleates 3a-d and -fumarates 4a-c have been studied by steady-state photolysis, product analysis, and by laser flash photolysis. The formation of the different pyrrolidone derivatives in these reactions could be understood in terms of azomethine ylide intermediates 5a-d, which undergo facile 1,2-rearrangements leading to Schiff bases and their subsequent cyclization, followed by further transformations. Laser flash photolysis studies substantiate the formation of azomethine ylide intermediates from these substrates under direct irradiation; however, they are not formed under triplet sensitization by aromatic ketones. Geometric isomerization of the ethylenic diester moiety takes place both under direct and sensitized irradiations.