indolo<1,7-ab><1>benzazepine | 87941-08-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: indolo<1,7-ab><1>benzazepine
• 英文别名: 1-Azatetracyclo[8.6.1.02,7.014,17]heptadeca-2,4,6,8,10,12,14(17)-heptaene
• CAS: 87941-08-0
• 化学式: C₁₆H₁₃N
• 分子量: 219.286
• InChiKey: TVVVPFCQCPUQPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  indolo<1,7-ab><1>benzazepine 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 5H-indolo<1,7-ab><1>benzazepine
  参考文献：
  名称：

  Cationic Au(I)-Catalyzed Cycloisomerization of N-(2-Alkynylphenyl)indolines for the Construction of Indolobenzazepine Skeleton

  摘要：

  An intramolecular reaction of N-(2-alkynylphenyl)indolines proceeded efficiently to give indolo[1,7-ab][1]benzazepine derivatives in high to excellent yields by cationic Au(I)-catalyzed 7-endo-dig selective cycloisomerization along with DDQ oxidation. The present transformation could be used for the intramolecular reaction of N-(2-alkynylpheny1)-1,2,3,4-tetrahydroquinoline and N-(2-alkynylphenyl)-N-methylaniline, and construction of a dibenzazepine skeleton was achieved.

  DOI：

  10.3987/com-17-13793
• 作为产物：
  描述：

  1-(2-ethynylphenyl)indoline 在 吡啶 、 silver tetrafluoroborate 、 [ClAuP(C6F5)3] 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 indolo<1,7-ab><1>benzazepine
  参考文献：
  名称：

  Cationic Au(I)-Catalyzed Cycloisomerization of N-(2-Alkynylphenyl)indolines for the Construction of Indolobenzazepine Skeleton

  摘要：

  An intramolecular reaction of N-(2-alkynylphenyl)indolines proceeded efficiently to give indolo[1,7-ab][1]benzazepine derivatives in high to excellent yields by cationic Au(I)-catalyzed 7-endo-dig selective cycloisomerization along with DDQ oxidation. The present transformation could be used for the intramolecular reaction of N-(2-alkynylpheny1)-1,2,3,4-tetrahydroquinoline and N-(2-alkynylphenyl)-N-methylaniline, and construction of a dibenzazepine skeleton was achieved.

  DOI：

  10.3987/com-17-13793

文献信息

• US3966762A
  申请人：——

  公开号：US3966762A

  公开（公告）日：1976-06-29
• US3963721A
  申请人：——

  公开号：US3963721A

  公开（公告）日：1976-06-15
• Cationic Au(I)-Catalyzed Cycloisomerization of N-(2-Alkynylphenyl)indolines for the Construction of Indolobenzazepine Skeleton
  作者：Takanori Shibata、Mamoru Ito、Daisuke Inoue、Ryosuke Kawasaki、Kyalo Stephen Kanyiva

  DOI：10.3987/com-17-13793

  日期：——

  An intramolecular reaction of N-(2-alkynylphenyl)indolines proceeded efficiently to give indolo[1,7-ab][1]benzazepine derivatives in high to excellent yields by cationic Au(I)-catalyzed 7-endo-dig selective cycloisomerization along with DDQ oxidation. The present transformation could be used for the intramolecular reaction of N-(2-alkynylpheny1)-1,2,3,4-tetrahydroquinoline and N-(2-alkynylphenyl)-N-methylaniline, and construction of a dibenzazepine skeleton was achieved.