2-isopropyl-4-methylquinoline-3-carboxylic acid | 1443288-49-0

• 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-isopropyl-4-methylquinoline-3-carboxylic acid
• 英文别名: 4-methyl-2-propan-2-ylquinoline-3-carboxylic acid
• CAS: 1443288-49-0
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: ZKKSDYMPVSVJKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  异丁酰醋酸甲酯 、 邻氨基苯乙酮 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 24.0h， 以11%的产率得到2-isopropyl-4-methylquinoline-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

• [EN] SUBSTITUTED QUINOLINE-3-CARBOXAMIDES AS KCNQ2/3 MODULATORS<br/>[FR] QUINOLINE-3-CARBOXAMIDES SUBSTITUÉS EN TANT QUE MODULATEURS DE KCNQ2/3
  申请人：GRUENENTHAL GMBH

  公开号：WO2012025238A1

  公开（公告）日：2012-03-01

  The invention relates to substituted quinoline-3-carboxamides of formula (I) as KCNQ2/3 modulators for use in the treatment and/or prophylaxis of pain and relates diseases and/or disorders.

  该发明涉及用于治疗和/或预防疼痛及相关疾病和/或疾病的化合物，其为式(I)的取代喹啉-3-羧酰胺，作为KCNQ2/3调节剂。
• Substituted quinoline-3-carboxamides as KCNQ2/3 modulators
  申请人：Kühnert Sven

  公开号：US20120053204A1

  公开（公告）日：2012-03-01

  The invention relates to substituted quinoline-3-carboxamides, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

  该发明涉及替代喹啉-3-羧酰胺，包含这些化合物的药物组合物，以及这些化合物在治疗和/或预防疼痛以及其他疾病和/或紊乱中的用途。
• SUBSTITUTED QUINOLINE-3-CARBOXAMIDES AS KCNQ2/3 MODULATORS
  申请人：Grünenthal GmbH

  公开号：EP2609085A1

  公开（公告）日：2013-07-03
• US8445512B2
  申请人：——

  公开号：US8445512B2

  公开（公告）日：2013-05-21