1,3-diphenyl-9-methylcarbazole

• 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: 1,3-diphenyl-9-methylcarbazole
• 英文别名: 9-Methyl-1,3-diphenylcarbazole
• 化学式: C₂₅H₁₉N
• 分子量: 333.433
• InChiKey: YFRWKZHKZNKWAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 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 、 反式-查耳酮 在 正丁基锂 、 amberlyst-15 作用下， 生成 1,3-diphenyl-9-methylcarbazole
  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

文献信息

• Iodine-Catalyzed Regioselective Synthesis of Diphenyl-Substituted Carbazoles via [4 + 2] Annulation of β-Formyl Ketones with Indoles
  作者：Sundaram Suresh、Hung-Sheng Chien、Chao-Hua Chen、Hao-Yu Tsai、Dai-Ru Chung、Veerababurao Kavala、Ching-Fa Yao

  DOI：10.1021/acs.joc.3c01857

  日期：2023.12.15

  β-formyl ketones with an indole has been developed for the regioselective synthesis of diphenyl-substituted carbazoles in the presence of a catalytic amount of iodine. The 1,4-dicarbonyl compound containing a phenyl group at the α-position of an aldehyde group reacts more readily with indoles to form carbazole derivatives. Using this method, a variety of carbazole derivatives can be readily accessed

  β-甲酰酮与吲哚的[4 + 2]环化已被开发用于在催化量的碘存在下区域选择性合成二苯基取代的咔唑。醛基的α位含有苯基的1，4-二羰基化合物更容易与吲哚反应生成咔唑衍生物。利用该方法，可以在温和的反应条件下容易地获得多种咔唑衍生物。