7-ethoxycarbonyl-9-hydroxy-2,3,5-trimethyl-1H-pyrrolo[2,3-f]quinoline | 898127-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-ethoxycarbonyl-9-hydroxy-2,3,5-trimethyl-1H-pyrrolo[2,3-f]quinoline
• 英文别名: 1H-Pyrrolo[2,3-f]quinoline-7-carboxylic acid, 6,9-dihydro-2,3,5-trimethyl-9-oxo-, ethyl ester；ethyl 2,3,5-trimethyl-9-oxo-1,6-dihydropyrrolo[2,3-f]quinoline-7-carboxylate
• CAS: 898127-53-2
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: LIIZEDDUZSXQRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  diethyl (2-Z)-2-(2,3,5-trimethyl-1H-indol-6-ylamino)-2-butenedioate 以 联苯 为溶剂， 反应 0.17h， 以58%的产率得到7-ethoxycarbonyl-9-hydroxy-2,3,5-trimethyl-1H-pyrrolo[2,3-f]quinoline
  参考文献：
  名称：

  由取代的6-氨基吲哚和草酰乙酸酯合成吡咯并喹啉

  摘要：

  It was established that the initial condensation of substituted 6-aminoindoles and oxaloacetic ester in boiling benzene with the addition of catalytic amounts of acetic acid takes place exclusively through the carboxyl group of the keto ester with the formation of the corresponding enamines, which successfully undergo thermal cyclization (biphenyl, 280 degrees C) to pyrroloquinolines. Here, irrespective of the nature of substituents at the N-1 and C-5 atoms enamines with a free position 7 are transformed into pyrrolo-[2,3-f]quinolines (structural analogs of vitamin PQQ) while 7-OMe-substituted enamines give pyrrolo[3,2-g]quinolines with linear fusion of the rings.

  DOI：

  10.1007/s10593-008-0111-8

文献信息

• Synthesis of pyrroloquinolines from substituted 6-aminoindoles and oxaloacetic ester
  作者：S. A. Yamashkin、N. V. Zhukova、I. S. Romanova

  DOI：10.1007/s10593-008-0111-8

  日期：2008.7

  It was established that the initial condensation of substituted 6-aminoindoles and oxaloacetic ester in boiling benzene with the addition of catalytic amounts of acetic acid takes place exclusively through the carboxyl group of the keto ester with the formation of the corresponding enamines, which successfully undergo thermal cyclization (biphenyl, 280 degrees C) to pyrroloquinolines. Here, irrespective of the nature of substituents at the N-1 and C-5 atoms enamines with a free position 7 are transformed into pyrrolo-[2,3-f]quinolines (structural analogs of vitamin PQQ) while 7-OMe-substituted enamines give pyrrolo[3,2-g]quinolines with linear fusion of the rings.