Phenyl-(5aR,10aR)-6,9,10,10a-tetrahydro-5aH-cyclohepta[b]indol-5-yl-methanone | 135733-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Phenyl-(5aR,10aR)-6,9,10,10a-tetrahydro-5aH-cyclohepta[b]indol-5-yl-methanone
• CAS: 135733-80-1
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: IWFRCEIMUWXADM-SJLPKXTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  N-benzoylindole 、 乙烯基环丙烷 以 苯 为溶剂， 反应 122.0h， 以2 mg的产率得到((1R,2aS,7bS)-1-Cyclopropyl-1,2,2a,7b-tetrahydro-cyclobuta[b]indol-3-yl)-phenyl-methanone
  参考文献：
  名称：

  Structures and lifetimes of 1,4-biradical intermediates in the photochemical cycloaddition reactions of N-benzoylindole with alkenes

  摘要：

  The photochemical cycloaddition reaction of N-benzoylindole with 1,6-heptadiene, tetramethylethylene, and vinylcyclopropane has been examined. The structures of the products suggest that the reaction proceeds via a 1,4-biradical intermediate that is formed by bonding between one terminus of the alkene and the 2-position of the indole derivative. This result is used to explain the origin of the previously observed regioselectivity of the photochemical cycloaddition reaction. The biradical intermediates obtained in the photochemical cycloaddition reaction of N-benzoylindole with vinylcyclopropane and 1,6-heptadiene can undergo rearrangement reactions whose rate constants can be estimated. Using these rates as clocks, the lifetimes of the intermediate biradicals in the photochemical cycloaddition reaction of N-benzoylindole with alkenes are estimated to be of the order of 100 ns. The consequences of this for the potential success of synthetically useful trapping of the intermediate biradicals is discussed.

  DOI：

  10.1021/jo00022a021