2,3-dihydro-1,6-dimethyl-3,5-diphenyl-1H-azepine | 1608154-87-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 2,3-dihydro-1,6-dimethyl-3,5-diphenyl-1H-azepine
• 英文别名: 1,6-Dimethyl-3,5-diphenyl-2,3-dihydroazepine；1,6-dimethyl-3,5-diphenyl-2,3-dihydroazepine
• CAS: 1608154-87-5
• 化学式: C₂₀H₂₁N
• 分子量: 275.393
• InChiKey: SSYWFOVOVJEKOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  肌氨酸 、 (2E,4E)-3,5-diphenyl-2-methylpenta-2,4-dienal 以 甲苯 为溶剂， 反应 16.0h， 以76%的产率得到2,3-dihydro-1,6-dimethyl-3,5-diphenyl-1H-azepine
  参考文献：
  名称：

  An investigation of the scope of the 1,7-electrocyclization of α,β:γ,δ-conjugated azomethine ylides

  摘要：

  Substituents on the diene component have little influence on the periselectivity of the cyclizations of alpha,beta:gamma,delta-conjugated azomethine ylides, with 1,7-electrocyclizations predominating. In some cases, subtle changes to these substituents can, however, influence the product formed, through their effect on the relative energies of the transition states for the 1,5- (6 pi) and 1,7-electrocyclization (8 pi) processes. The most striking changes in periselectivity occur for phenylethenyl-substituted azomethine ylides 3d-f, which can give either a pyrroline 4d,f or dihydrobenzazepine 6e, depending upon the alkene configuration. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.078

文献信息

• An investigation of the scope of the 1,7-electrocyclization of α,β:γ,δ-conjugated azomethine ylides
  作者：Weimin Zhang、Fuqiang Ning、Linda Váradi、David E. Hibbs、James A. Platts、Miklós Nyerges、Rosaleen J. Anderson、Paul W. Groundwater

  DOI：10.1016/j.tet.2014.03.078

  日期：2014.6

  Substituents on the diene component have little influence on the periselectivity of the cyclizations of alpha,beta:gamma,delta-conjugated azomethine ylides, with 1,7-electrocyclizations predominating. In some cases, subtle changes to these substituents can, however, influence the product formed, through their effect on the relative energies of the transition states for the 1,5- (6 pi) and 1,7-electrocyclization (8 pi) processes. The most striking changes in periselectivity occur for phenylethenyl-substituted azomethine ylides 3d-f, which can give either a pyrroline 4d,f or dihydrobenzazepine 6e, depending upon the alkene configuration. (C) 2014 Elsevier Ltd. All rights reserved.