1-[1-(1-Methyl-1H-indol-3-yl)-ethyl]-1H-benzotriazole | 161533-28-4

• 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: 1-[1-(1-Methyl-1H-indol-3-yl)-ethyl]-1H-benzotriazole
• 英文别名: 1-[1-(1-methylindol-3-yl)ethyl]benzotriazole
• CAS: 161533-28-4
• 化学式: C₁₇H₁₆N₄
• 分子量: 276.341
• InChiKey: LYXOYACXEXJGTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Alpha-甲基苯乙烯 、 1-[1-(1-Methyl-1H-indol-3-yl)-ethyl]-1H-benzotriazole 在 zinc dibromide 作用下， 生成 (1R,3R)-1,4-Dimethyl-3-p-tolyl-1,2,3,4-tetrahydro-cyclopenta[b]indole 、 (1S,3R)-1,4-Dimethyl-3-p-tolyl-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
• 作为产物：
  描述：

  1-[(1-methyl-1H-indol-3-yl)methyl]-1H-1,2,3-benzotriazole 、 碘甲烷 在 正丁基锂 作用下， 生成 1-[1-(1-Methyl-1H-indol-3-yl)-ethyl]-1H-benzotriazole
  参考文献：
  名称：

  A Versatile Synthesis of 3-Substituted Indoles

  摘要：

  A variety of 3-substituted indoles are prepared from 1-methyl-3-(benzotriazol-1-ylalkyl)indoles (1), which are readily available either from the condensation of 3-methylindole with N-(benzotriazol-1-ylalkyl)carbamates or from the alkylation and silylation of lithiated 1-methyl-3-(benzotriazol-1-ylmethyl)indole (2).

  DOI：

  10.1080/00397919508011388

文献信息

• A Versatile Synthesis of 3-Substituted Indoles
  作者：Alan R. Katritzky、Linghong Xie、Darren Cundy

  DOI：10.1080/00397919508011388

  日期：1995.2

  A variety of 3-substituted indoles are prepared from 1-methyl-3-(benzotriazol-1-ylalkyl)indoles (1), which are readily available either from the condensation of 3-methylindole with N-(benzotriazol-1-ylalkyl)carbamates or from the alkylation and silylation of lithiated 1-methyl-3-(benzotriazol-1-ylmethyl)indole (2).
• Efficient Syntheses of Substituted Carbazoles and Cyclopent[<i>b</i>]indoles from 1-Methyl-3-(benzotriazol-1-ylmethyl)indole
  作者：Alan R. Katritzky、Guifen Zhang、Linghong Xie、Ion Ghiviriga

  DOI：10.1021/jo9604954

  日期：1996.1.1

  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.