ethyl 4-[2-chloro-3-(trifluoromethyl)phenyl]-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate | 1364365-14-9

• 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: ethyl 4-[2-chloro-3-(trifluoromethyl)phenyl]-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• CAS: 1364365-14-9
• 化学式: C₂₀H₁₉ClF₃NO₃
• 分子量: 413.824
• InChiKey: NTDMQOPJKSEFMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-氯-3-(三氟甲基)苯甲醛 、 乙酰乙酸乙酯 、 1,3-环己二酮 在 iron(III) trifluoride 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以85%的产率得到ethyl 4-[2-chloro-3-(trifluoromethyl)phenyl]-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  FeF3 as a novel catalyst for the synthesis of polyhydroquinoline derivatives via unsymmetrical Hantzsch reaction

  摘要：

  A facile and highly efficient one-pot synthesis of polyhydroquinoline derivatives is reported via four-component condensation reaction of aldehydes, beta-keto compounds, active methylene compounds and ammonium acetate in the presence of FeF3 as a catalyst in ethanol at 75-80 degrees C. The method offers several advantages including high yields, short reaction time, simple work-up procedure and catalyst reusability for several runs. The higher catalytic activity of FeF3 ascribed due to its high acidity, thermal stability and water tolerance. The superiority of use of FeF3 to the current process is compared with other Lewis acids, Fe-salts, fluoride sources and insights of the origin of the efficiency are discussed. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.09.005