5-Cyclopropylamino-4-hydroxy-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester | 136342-78-4

• 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-Cyclopropylamino-4-hydroxy-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester
• CAS: 136342-78-4
• 化学式: C₂₀H₁₉N₃O₇
• 分子量: 413.387
• InChiKey: XYRJPWDNOPWLTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  139.84
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  4,5-二氧代-4,5-二氢-1H-吡咯[2,3-f]喹啉-2,7,9-三羧酸三甲酯 在 甲基肼 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 5-Cyclopropylamino-4-hydroxy-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester
  参考文献：
  名称：

  Reaction of the trimethyl ester of coenzyme PQQ(PQQTME) and amines in organic media. Products and mechanism

  摘要：

  The reaction of PQQTME (1, the trimethyl ester of coenzyme PQQ) and various amines in organic media was investigated in order to gain information on the chemistry of PQQ in vitro. The iminoquinone derivatives 2, 3, and 5 were isolated from the reaction of 1 with ammonia, tert-butylamine, and cyclopropylamine, respectively, in CH3CN. The reduction of 2 by methylhydrazine proceeded smoothly to give the aminophenol 2H2 in moderate yield. Detailed analysis of the products from the reaction of 1 (and its 1-methyl derivative 6) with n-propylamine, N-methylpropylamine, triethylamine, and several benzylamines established that the oxidation of amines by PQQTME proceeds via an ionic mechanism (addition-elimination and transamination) that involves a carbinolamine intermediate. PQQTME was also found to be an efficient turnover catalyst of the aerobic oxidation of benzylamines in CH3CN solution.

  DOI：

  10.1021/jo00024a030