1,3,5-Trimethyl-3,4-diphenyl-1,3-dihydro-pyrrol-2-one | 143841-06-9

• 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: 1,3,5-Trimethyl-3,4-diphenyl-1,3-dihydro-pyrrol-2-one
• 英文别名: 1,3,5-trimethyl-3,4-diphenylpyrrol-2-one
• CAS: 143841-06-9
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: PYEVBGNKWHNGOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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 1,3,5-Trimethyl-3,4-diphenyl-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