5,6,11,12-tetramethyl-5,6,11,12-tetrahydro-indolo[3,2-b]carbazole | 29124-12-7

• 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: 5,6,11,12-tetramethyl-5,6,11,12-tetrahydro-indolo[3,2-b]carbazole
• 英文别名: 5,6,11,12-Tetrahydro-5,6,11,12-tetramethylindolo[3,2-b]carbazole；5,6,11,12-tetramethyl-6,12-dihydroindolo[3,2-b]carbazole
• CAS: 29124-12-7
• 化学式: C₂₂H₂₂N₂
• 分子量: 314.43
• InChiKey: XZPWFFHKURNLQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-[1-(1-Methyl-1H-indol-2-yl)-ethyl]-1H-benzotriazole 在 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到5,6,11,12-tetramethyl-5,6,11,12-tetrahydro-indolo[3,2-b]carbazole
  参考文献：
  名称：

  Facile Synthesis of 2-Substituted Indoles and Indolo[3,2-b]carbazoles from 2-(Benzotriazol-1-ylmethyl)indole

  摘要：

  Replacement of the benzotriazole moiety of N-alkyl-2-(1-benzotriazol-1-ylalkyl)indo 6 and 9, prepared from 1-propargylbenzotriazole and o-iodoaniline followed by alkylation, with Grignard reagents gave the corresponding 2-substituted indoles 10 in good yield. Treatment of compounds 6 or 9 with zinc chloride afforded 6,12-disubstituted-6,12-dihydroindolo[3,2-b]carbazoles 11 in moderate to good yields. 6,12-Disubstituted-5,11-dihydroindolo[3,2-b]carbazoles 13 were prepared readily and in good yield from 2-(benzotriazol-1-ylalkyl)indoles 8 via dimerization in the presence of zinc chloride followed by dehydrogenation on exposure to air.

  DOI：

  10.1021/jo00116a026

文献信息

• Indolecarbonyl Coupling Reactions Promoted by Samarium Diiodide. Application to the Synthesis of Indole-Fused Compounds
  作者：Shu-Chen Lin、Fwu-Duo Yang、Jiann-Shyng Shiue、Shyh-Ming Yang、Jim-Min Fang

  DOI：10.1021/jo9720795

  日期：1998.5.1

  By the assistance of an N-sulfonyl group or a cyano group at the C-2 position, hydroxyalkylations of indole-3-carbonyls were achieved by the promotion of samarium diiodide. The indolecarbonyl coupling reactions proceeded in high stereoselectivity via chelate transition states. Intramolecular indolecarbonyl couplings of 1-(3-oxopropyl)indole-3-carboxaldehydes were realized as the indole-carbonyl group was more reactive toward SmI2 than the aliphatic carbonyl group. Elaboration of the coupling products with oxidizing agents, acid, phosphorus pentasulfide (or Lawesson's reagent), amines, and hydrazine led to a variety of indole derivatives and indole-fused polycyclic compounds of synthetic interest and pharmaceutical uses.