4-chloro-6-fluoro-2-(2-hydroxyphenyl)quinoline | 178990-45-9

• 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: 4-chloro-6-fluoro-2-(2-hydroxyphenyl)quinoline
• 英文别名: 2-(4-Chloro-6-fluoroquinolin-2-yl)phenol
• CAS: 178990-45-9
• 化学式: C₁₅H₉ClFNO
• 分子量: 273.694
• InChiKey: XCFWXFHYJGYRFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-6-fluoro-2-(2-hydroxyphenyl)quinoline 在 sodium hydroxide 、 盐酸羟胺 、 溶剂黄146 作用下， 以 乙二醇乙醚 为溶剂， 反应 11.5h， 生成 2-[6-Fluoro-4-[4-(3-methyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]quinolin-2-yl]phenol
  参考文献：
  名称：

  Oxadiazoles as bioisosteric transformations of carboxylic functionalities. II

  摘要：

  In order to improve the in vivo efficacy of a series of known benzodiazepine receptor (BZR) ligands, 1-(2-phenyl-4-quinolinyl)-4-piperidinecarboxamides, a series of analogs has been prepared in which the amide group of these ligands has been replaced by a 1,2,4-oxadiazole moiety or converted to other carboxylic isosters such as esters or nitriles. An increase in the in vivo efficacy was observed for some of the compounds prepared in this investigation compared to the parent carboxamide derivatives.

  DOI：

  10.1016/0223-5234(96)89169-0
• 作为产物：
  描述：

  4-氯-6-氟喹啉 在 sodium hydroxide 、 正丁基锂 、 碘 、 三溴化硼 作用下， 以 甲苯 为溶剂， 反应 5.17h， 生成 4-chloro-6-fluoro-2-(2-hydroxyphenyl)quinoline
  参考文献：
  名称：

  Oxadiazoles as bioisosteric transformations of carboxylic functionalities. II

  摘要：

  In order to improve the in vivo efficacy of a series of known benzodiazepine receptor (BZR) ligands, 1-(2-phenyl-4-quinolinyl)-4-piperidinecarboxamides, a series of analogs has been prepared in which the amide group of these ligands has been replaced by a 1,2,4-oxadiazole moiety or converted to other carboxylic isosters such as esters or nitriles. An increase in the in vivo efficacy was observed for some of the compounds prepared in this investigation compared to the parent carboxamide derivatives.

  DOI：

  10.1016/0223-5234(96)89169-0