(+/-)-4-amino-1,3,4,5-tetrahydrobenzindole-4-carboxylic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-4-amino-1,3,4,5-tetrahydrobenzindole-4-carboxylic acid
• 英文别名: 4-amino-1,3,4,5-tetrahydrobenz[cd]indole-4-carboxylic acid；4-amino-3,5-dihydro-1H-benzo[cd]indole-4-carboxylic acid
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: YRBGHAUHNNDEER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,5-dihydrobenzindol-4(3H)-one 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 27.0h， 生成 (+/-)-4-amino-1,3,4,5-tetrahydrobenzindole-4-carboxylic acid
  参考文献：
  名称：

  Synthesis of 4-Amino-, 4-Hydroxy-, and 4-Nitro-1,3,4,5-tetrahydrobenz[cd]indols and Its Bromination

  摘要：

  Simple synthetic method for 4-nitro-1,3,4,5-tetrahydrobenz[cd]indole (6) is established from indole-3-carboxaldehyde (7). With 6 in hand, various derivatives of 4-amino-, 4-hydroxy- and 4-amino-4-hydroxymethyl-1,3,4,5-tetrahydrobenz[cd]indoles become readily available. Bromination of 6 afforded useful building blocks for further manipulation. Successful optical resolution of 6 by chiral column chromatography is also reported.

  DOI：

  10.3987/com-13-s(s)74

文献信息

• Syntheses of (±)-4-Amino-1,3,4,5-tetrahydrobenz[cd]indole-4-carboxylic Acid, (±)-4-N,N-Dipropylamino-4-hydroxymethyl- and (±)-4-Propyloxy-1,3,4,5-tetrahydrobenz[cd]indole
  作者：Masanori Somei、Naokatsu Aoki、Kyoko Nakagawa

  DOI：10.3987/com-94-6738

  日期：——

  Simple syntheses of the title compounds are reported starting from indole-3-carboxaldehyde.
• Synthesis of 4-Amino-, 4-Hydroxy-, and 4-Nitro-1,3,4,5-tetrahydrobenz[cd]indols and Its Bromination
  作者：Masanori Somei、Kyoko Nakagawa、Naokatsu Aoki、Harunobu Mukaiyama

  DOI：10.3987/com-13-s(s)74

  日期：——

  Simple synthetic method for 4-nitro-1,3,4,5-tetrahydrobenz[cd]indole (6) is established from indole-3-carboxaldehyde (7). With 6 in hand, various derivatives of 4-amino-, 4-hydroxy- and 4-amino-4-hydroxymethyl-1,3,4,5-tetrahydrobenz[cd]indoles become readily available. Bromination of 6 afforded useful building blocks for further manipulation. Successful optical resolution of 6 by chiral column chromatography is also reported.