2-propylquinoline-3-carboxylic acid | 1482555-94-1

• 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: 2-propylquinoline-3-carboxylic acid
• 英文别名: 2-Propylquinoline-3-carboxylic acid
• CAS: 1482555-94-1
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: SYTMCKFYAIUFGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基苯甲醛 、 3-氧代己酸甲酯 以 甲苯 为溶剂， 反应 24.0h， 以86%的产率得到2-propylquinoline-3-carboxylic acid
  参考文献：
  名称：

  Quinoline- and 1,8-naphthyridine-3-carboxylic acids using a self-catalyzed Friedländer approach

  摘要：

  One-step syntheses of 2-alkyl- and 2,4-dialkyl-substituted quinoline-3-carboxylic acids and 1,8-naphthyridine-3-carboxylic acids are reported using a catalyst-free Friedlander reaction. The reaction is carried out in one step by simple heating of 2-aminobenzaldehyde, 2-amino-5-chlorobenzaldehyde, 2-aminonicotinaldehyde, or 2-aminoacetophenone with a beta-ketoester in toluene or xylene for 24 h. Under these conditions, the carboxylic acid product is isolated directly from the reaction mixture without need for further purification. The observation that the reaction starts slowly and accelerates as it proceeds suggests that the transformation is self-catalyzed. This hypothesis is also supported by the finding that attempts to extend the current reaction to diketones, which cannot hydrolyze to an acid, were generally unsuccessful. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.010

文献信息

• Quinoline- and 1,8-naphthyridine-3-carboxylic acids using a self-catalyzed Friedländer approach
  作者：Baskar Nammalwar、Maeghan Murie、Chelsea Fortenberry、Richard A. Bunce

  DOI：10.1016/j.tetlet.2014.04.010

  日期：2014.5

  One-step syntheses of 2-alkyl- and 2,4-dialkyl-substituted quinoline-3-carboxylic acids and 1,8-naphthyridine-3-carboxylic acids are reported using a catalyst-free Friedlander reaction. The reaction is carried out in one step by simple heating of 2-aminobenzaldehyde, 2-amino-5-chlorobenzaldehyde, 2-aminonicotinaldehyde, or 2-aminoacetophenone with a beta-ketoester in toluene or xylene for 24 h. Under these conditions, the carboxylic acid product is isolated directly from the reaction mixture without need for further purification. The observation that the reaction starts slowly and accelerates as it proceeds suggests that the transformation is self-catalyzed. This hypothesis is also supported by the finding that attempts to extend the current reaction to diketones, which cannot hydrolyze to an acid, were generally unsuccessful. (C) 2014 Elsevier Ltd. All rights reserved.