3,4-Dimethyl-3-phenyl-1,2,3,4-tetrahydro-cyclopenta[b]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: 3,4-Dimethyl-3-phenyl-1,2,3,4-tetrahydro-cyclopenta[b]indole
• 英文别名: 3,4-Dimethyl-3-phenyl-1,2-dihydrocyclopenta[b]indole
• 化学式: C₁₉H₁₉N
• 分子量: 261.367
• InChiKey: VHDSDUMBRUTHCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-[(1-methyl-1H-indol-3-yl)methyl]-1H-1,2,3-benzotriazole 、 2-苯基-1-丙烯 在 zinc dibromide 作用下， 生成 3,4-Dimethyl-3-phenyl-1,2,3,4-tetrahydro-cyclopenta[b]indole
  参考文献：
  名称：

  Efficient Syntheses of Substituted Carbazoles and Cyclopent[b]indoles from 1-Methyl-3-(benzotriazol-1-ylmethyl)indole

  摘要：

  1-Methyl-3-(benzotriazol-1-ylmethyl)indole (1)undergoes lithiation and 1,4-addition with a variety of alpha,beta-unsaturated ketones and aldehydes. Subsequent treatment with an acidic resin in refluxing 1,4-dioxane causes intramolecular cyclization followed by aromatization to furnish a wide range of 1.3-di-, 2,3-di- and 1,2,3-trisubstituted carbazoles 6a-j and 8 in moderate to excellent yields. NMR study is described to discriminate between structures of types 6 and 8 on the basis of H-1-C-13 long-range correlation. Treatment of 1 with styrenes in the presence of zinc bromide results in formal [3+2] cycloaddition to give cyclopent[b]indoles 14a-c in good yields. When 1 is first lithiated and reacts with electrophiles, the resulting alkylation products undergo similar [3+2] additions with styrenes to give 1-functionalized cyclopent[b]indoles 15 and 16 with a high degree of stereoselectivity.

  DOI：

  10.1021/jo9604954