dimethyl 1-(cis-2-benzyl-2,3-diphenylaziridyl)maleate | 143632-03-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: dimethyl 1-(cis-2-benzyl-2,3-diphenylaziridyl)maleate
• 英文别名: dimethyl (E)-2-[(2R,3S)-2-benzyl-2,3-diphenylaziridin-1-yl]but-2-enedioate
• CAS: 143632-03-5
• 化学式: C₂₇H₂₅NO₄
• 分子量: 427.5
• InChiKey: YZCIWKOPCOYYFM-TZLFHBCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 1-(cis-2-benzyl-2,3-diphenylaziridyl)maleate 以 苯 为溶剂， 反应 12.0h， 以60%的产率得到(E)-2-(1,2-Diphenyl-1-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethyl)-but-2-enedioic acid dimethyl ester
  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：

  (2R,3S)-2-Benzyl-2,3-diphenyl-aziridine 、 丁炔二酸二甲酯 以 苯 为溶剂， 反应 12.0h， 以78%的产率得到dimethyl 1-(cis-2-benzyl-2,3-diphenylaziridyl)maleate
  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.