9-benzyl-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole

• 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: 9-benzyl-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole
• 英文别名: 9-benzyl-6-methoxy-1,2,3,4-tetrahydrocarbazole
• 化学式: C₂₀H₂₁NO
• mdl: MFCD00512752
• 分子量: 291.393
• InChiKey: HSLQLJZTDTVTDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  tert-butyl 2-benzyl-2-(4-methoxyphenyl)hydrazine carboxylate 、 环己酮 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 4.75h， 以83%的产率得到9-benzyl-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole
  参考文献：
  名称：

  Zinc-Mediated Allylation and Benzylation of Phenylazocarboxylic Esters

  摘要：

  Allylation and benzylation of phenylazocarboxylic tert-butyl esters have been achieved under Barbier-type reaction conditions and in very short reactions times using the corresponding allyl and benzyl bromides or iodides in combination with zinc powder. Whereas all reactions occurred exclusively at the beta-nitrogen atom of the azocarboxylic esters, the linkage of allyl units was shown to depend on the substitution pattern at the double bond of the allyl halide. The hydrazines obtained are useful precursors for indoles and indazoles.

  DOI：

  10.1021/acs.joc.5b01978

文献信息

• Zinc-Mediated Allylation and Benzylation of Phenylazocarboxylic Esters
  作者：Roman Lasch、Markus R. Heinrich

  DOI：10.1021/acs.joc.5b01978

  日期：2015.10.16

  Allylation and benzylation of phenylazocarboxylic tert-butyl esters have been achieved under Barbier-type reaction conditions and in very short reactions times using the corresponding allyl and benzyl bromides or iodides in combination with zinc powder. Whereas all reactions occurred exclusively at the beta-nitrogen atom of the azocarboxylic esters, the linkage of allyl units was shown to depend on the substitution pattern at the double bond of the allyl halide. The hydrazines obtained are useful precursors for indoles and indazoles.