cis-3-methyl-4-phenyl-1-benzhydrylazetidin-2-one | 88047-76-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: cis-3-methyl-4-phenyl-1-benzhydrylazetidin-2-one
• 英文别名: 2-Azetidinone, 1-(diphenylmethyl)-3-methyl-4-phenyl-, cis-；(3S,4S)-1-benzhydryl-3-methyl-4-phenylazetidin-2-one
• CAS: 88047-76-1
• 化学式: C₂₃H₂₁NO
• 分子量: 327.426
• InChiKey: IVGJSUZNOVTRSQ-UWJYYQICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  cis-3-methyl-4-phenyl-1-benzhydrylazetidine-2-(N-dimethyliminium perchlorate) 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 以41%的产率得到cis-3-methyl-4-phenyl-1-benzhydrylazetidin-2-one
  参考文献：
  名称：

  Synthesis of 2-Azetidiniminium Salts. 1. Diastereoselectivity in Keteniminium Triflate/Imine Cycloadditions

  摘要：

  A systematic study of the synthesis of 2-azetidiniminium triflates, by annulation of aldimines with iminium salts derived from tertiary carboxamides and trifluoromethanesulfonic anhydride, has been carried out. The stereochemical output of a number of 2-azetidiniminium triflates is compared with that of the corresponding chloride salts synthesized by reaction of the same imines with a-chloro iminium chlorides. As a general rule, the stereochemical output of the reactions involving a-chloro iminium chlorides is in stark contrast to that of the corresponding triflates: while the chloride salts are trans stereoselective, the triflates show a preference for the cis products. The stereochemistry of the reactions involving the triflates has been examined in light of the structure of the reagents. Clear trends for a preferential formation of cis or trans products with the steric and electronic demand of the imine have been observed. By contrast, no correlation of the product distribution with the steric demand of the amide could be made. The transient formation of a keteniminium triflate intermediate has been suggested. According to this model, the annulation of the imine with the keteniminium triflates occurs with a mechanism closely similar to that observed in the Staudinger reaction. A comparison between the reactions involving the bona fide keteniminium triflates, and the corresponding isoelectronic ketenes with the same, or structurally closely related, imines has also been made. This comparison is performed in light of Georg's stereochemical rules that are used to explain, or predict, the stereochemical output of the Staudinger reaction.

  DOI：

  10.1021/jo9608782

文献信息

• A convenient synthesis of azetidine-2-thiones and azetidin-2-imines
  作者：Jacqueline Marchand-Brynaert、Manuel Moya-Portuguez、Isabelle Huber、L�on Ghosez

  DOI：10.1039/c39830000818

  日期：——

  Azetidin-2-iminium salts, which are readily available from tertiary amides, can be easily converted into the corresponding thiones or imines.

  可以从叔酰胺容易获得的氮杂环丁烷-2-亚胺盐可以容易地转化成相应的硫酮或亚胺。
• Synthesis of 2-Azetidiniminium Salts. 1. Diastereoselectivity in Keteniminium Triflate/Imine Cycloadditions
  作者：Gaetano Barbaro、Arturo Battaglia、Cristiana Bruno、Patrizia Giorgianni、Andrea Guerrini

  DOI：10.1021/jo9608782

  日期：1996.1.1

  A systematic study of the synthesis of 2-azetidiniminium triflates, by annulation of aldimines with iminium salts derived from tertiary carboxamides and trifluoromethanesulfonic anhydride, has been carried out. The stereochemical output of a number of 2-azetidiniminium triflates is compared with that of the corresponding chloride salts synthesized by reaction of the same imines with a-chloro iminium chlorides. As a general rule, the stereochemical output of the reactions involving a-chloro iminium chlorides is in stark contrast to that of the corresponding triflates: while the chloride salts are trans stereoselective, the triflates show a preference for the cis products. The stereochemistry of the reactions involving the triflates has been examined in light of the structure of the reagents. Clear trends for a preferential formation of cis or trans products with the steric and electronic demand of the imine have been observed. By contrast, no correlation of the product distribution with the steric demand of the amide could be made. The transient formation of a keteniminium triflate intermediate has been suggested. According to this model, the annulation of the imine with the keteniminium triflates occurs with a mechanism closely similar to that observed in the Staudinger reaction. A comparison between the reactions involving the bona fide keteniminium triflates, and the corresponding isoelectronic ketenes with the same, or structurally closely related, imines has also been made. This comparison is performed in light of Georg's stereochemical rules that are used to explain, or predict, the stereochemical output of the Staudinger reaction.