2,3-dihydro-2-(3,3-dimethyl-2-phenyl-1-butenylidene)-1,3,3-trimethyl-1H-indole

• 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: 2,3-dihydro-2-(3,3-dimethyl-2-phenyl-1-butenylidene)-1,3,3-trimethyl-1H-indole
• 化学式: C₂₃H₂₇N
• 分子量: 317.474
• InChiKey: HIWOVMGJDHWPCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  2,3-dihydro-2-(3,3-dimethyl-2-phenyl-1-butenylidene)-1,3,3-trimethyl-1H-indole 以 甲苯 为溶剂， 反应 2.0h， 以92%的产率得到11-tert-Butyl-13,13-dimethyl-12a,13-dihydro-6H-benzo[5,6]azepino[1,2-a]indole
  参考文献：
  名称：

  Tri- and Tetracyclic Azepine Derivatives by Thermally Induced Cyclization of Aminoallenes and Semicyclic 2-Dienamines

  摘要：

  The 3,3-dimethylindoline-derived allenes 5 are conveniently prepared by organocuprate addition to 2-(phenylethynyl)-3,3-dimethyl-1-methylindolium triflate 4. Their thermal isomerization affords tetracyclic azepine derivatives 6. The semicyclic 2-amino 1,3-dienes 11, formed by spontaneous tautomerization of the corresponding aminoallenes, are transformed by thermal reaction into either tricyclic azepine derivatives 13 or benzothiophene-annelated azaheterocycles 14 and 15, depending on the ring size of the enamine moiety and the (hetero)aryl group at C-4 of the 2-dienamine.

  DOI：

  10.1021/jo9710036
• 作为产物：
  描述：

  叔丁基锂 、 1,3,3-trimethyl-2-(2-phenylethynyl)-3H-indolium triflate 在 CuCN 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以84%的产率得到2,3-dihydro-2-(3,3-dimethyl-2-phenyl-1-butenylidene)-1,3,3-trimethyl-1H-indole
  参考文献：
  名称：

  Tri- and Tetracyclic Azepine Derivatives by Thermally Induced Cyclization of Aminoallenes and Semicyclic 2-Dienamines

  摘要：

  The 3,3-dimethylindoline-derived allenes 5 are conveniently prepared by organocuprate addition to 2-(phenylethynyl)-3,3-dimethyl-1-methylindolium triflate 4. Their thermal isomerization affords tetracyclic azepine derivatives 6. The semicyclic 2-amino 1,3-dienes 11, formed by spontaneous tautomerization of the corresponding aminoallenes, are transformed by thermal reaction into either tricyclic azepine derivatives 13 or benzothiophene-annelated azaheterocycles 14 and 15, depending on the ring size of the enamine moiety and the (hetero)aryl group at C-4 of the 2-dienamine.

  DOI：

  10.1021/jo9710036