3-Cyclopropyl-1-methyl-3,4,5-triphenyl-1,3-dihydro-pyrrol-2-one | 143841-08-1

• 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: 3-Cyclopropyl-1-methyl-3,4,5-triphenyl-1,3-dihydro-pyrrol-2-one
• 英文别名: 3-Cyclopropyl-1-methyl-3,4,5-triphenyl-1,3-dihydro-2H-pyrrol-2-one；3-cyclopropyl-1-methyl-3,4,5-triphenylpyrrol-2-one
• CAS: 143841-08-1
• 化学式: C₂₆H₂₃NO
• 分子量: 365.475
• InChiKey: KARXKROUCDVAMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  二苯基乙炔 、 alkaline earth salt of/the/ methylsulfuric acid 生成 3-Cyclopropyl-1-methyl-3,4,5-triphenyl-1,3-dihydro-pyrrol-2-one
  参考文献：
  名称：

  Reaction of aminocarbene complexes of chromium with alkynes. 1. Formation and rearrangement of ketene and nitrogen ylide complexes

  摘要：

  The title reactions of chromium-containing carbene complexes (CO)5Cr=C(R1)N(R2R3) (R1 = H, Me, Ph; R2 = Me; R3 = Me, C3H5, CH2C3H5; R2R3 = (CH2)5) 8 and (CO)5Cr=C[(CH2)3C=CPh]N(R1R2) (R1 = R2 = Me; R1R2 = (CH2)5; R1R2 = (CH2)4) 9, bearing alkyl groups of low migratory aptitude on nitrogen, have been examined. In contrast to complexes in which nitrogen bears either an alkyl and an allyl or a benzyl group or is part of a strained cycle, which give heterocycles upon alkyne/CO insertions followed by nitrogen-to-carbon migrations (e.g., 1 --> 7), complexes 8 and 9 lead to stable nitrogen ylides, which could be fully characterized by X-ray crystallography in the case of 8a and 9a. Moreover, in the case of complexes of the general structure 9, ketene precursors of the ylides could either be detected (R1 = Me; R2 = CH2Ph) or isolated and characterized (R2R3 = (CH2)5). The new ylide complexes undergo, upon moderate heating, Stevens-type rearrangements to the expected heterocyclic compounds as a result of nitrogen-to-carbon migrations of various alkyl groups, and upon treatment with dimethyldioxirane, they undergo oxidation to lactone complexes.

  DOI：

  10.1021/ja00047a018

文献信息

• Reaction of aminocarbene complexes of chromium with alkynes. 1. Formation and rearrangement of ketene and nitrogen ylide complexes
  作者：Evelyne Chelain、Regis Goumont、Louis Hamon、Andree Parlier、Michele Rudler、Henri Rudler、Jean Claude Daran、Jacqueline Vaissermann

  DOI：10.1021/ja00047a018

  日期：1992.10

  The title reactions of chromium-containing carbene complexes (CO)5Cr=C(R1)N(R2R3) (R1 = H, Me, Ph; R2 = Me; R3 = Me, C3H5, CH2C3H5; R2R3 = (CH2)5) 8 and (CO)5Cr=C[(CH2)3C=CPh]N(R1R2) (R1 = R2 = Me; R1R2 = (CH2)5; R1R2 = (CH2)4) 9, bearing alkyl groups of low migratory aptitude on nitrogen, have been examined. In contrast to complexes in which nitrogen bears either an alkyl and an allyl or a benzyl group or is part of a strained cycle, which give heterocycles upon alkyne/CO insertions followed by nitrogen-to-carbon migrations (e.g., 1 --> 7), complexes 8 and 9 lead to stable nitrogen ylides, which could be fully characterized by X-ray crystallography in the case of 8a and 9a. Moreover, in the case of complexes of the general structure 9, ketene precursors of the ylides could either be detected (R1 = Me; R2 = CH2Ph) or isolated and characterized (R2R3 = (CH2)5). The new ylide complexes undergo, upon moderate heating, Stevens-type rearrangements to the expected heterocyclic compounds as a result of nitrogen-to-carbon migrations of various alkyl groups, and upon treatment with dimethyldioxirane, they undergo oxidation to lactone complexes.