2,4-dibromo-9,10-dihydro-8H-azepino<1,2-a>indol-8-one | 34206-88-7

• 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: 2,4-dibromo-9,10-dihydro-8H-azepino<1,2-a>indol-8-one
• 英文别名: 6,7-Dihydroazepin<1,2-a>indol-8-on；6,7-Dihydroazepino<1.2-a>indol-8-on
• CAS: 34206-88-7
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: CLRJOQFKAKDYOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  22.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-azido-3,3',5-tribromo-4'-methoxydiphenylmethane 以 various solvent(s) 为溶剂， 反应 4.0h， 生成 2,4-dibromo-9,10-dihydro-8H-azepino<1,2-a>indol-8-one 、 2,4-dibromo-8H-azepino<1,2-a>indol-8-one 、 2,4-dibromo-8-methoxy-10H-azepino<1,2-a>indole 、 2,4,7-tribromo-8-methoxy-10H-azepino<1,2-a>indole
  参考文献：
  名称：

  Azoniaazulenes. Part 7. Functionalisation of 10H-azepino[1,2-a]indoles

  摘要：

  Direct functionalisation of azepinoindole 7 is described. Electrophilic attack by bromine, and by the Vilsmeier, Mannich, and Friedel-Crafts reagents gives 11 substituted azepinoindoles 8 and 11-14. From the bromo compound 8 an 11-lithioazepinoindole was obtained. With tert-butyllithium the azepinoindole 7 gave an allylic anion 36, which with trimethylsilyl (TMS) chloride gave the 8H-8-TMS derivative 16 and the 10H-8,10-bis-TMS derivative 17, for which an X-ray structure is provided. Alkylation of anion 36 gave mixtures of 8H-8-alkyl- and 10H-10-alkyl derivatives 18-25, while further lithiation of compound 16 and alkylation gave-mixtures of 8,8- and 8,10-disubstituted compounds 26-33. Decomposition of azide 43 gave eight identified products 44, 45, 47-51 and 54.

  DOI：

  10.1039/p19950000203