methyl (4E)-4-benzylidene-5-oxo-2-phenyl-1H-pyrrole-3-carboxylate | 1027834-47-4

• 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 (4E)-4-benzylidene-5-oxo-2-phenyl-1H-pyrrole-3-carboxylate
• CAS: 1027834-47-4
• 化学式: C₁₉H₁₅NO₃
• 分子量: 305.333
• InChiKey: UOSNUQMUQISBKO-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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 (4E)-4-benzylidene-5-oxo-2-phenyl-1H-pyrrole-3-carboxylate 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以86%的产率得到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 甲醇 、 苯 为溶剂， 反应 22.0h， 生成 methyl (4E)-4-benzylidene-5-oxo-2-phenyl-1H-pyrrole-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