ethyl 1,4,5,6,7,8-hexahydro-4-(1-naphthyl)-2-methyl-5-oxoquinoline-3-carboxylate | 299451-82-4

• 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 1,4,5,6,7,8-hexahydro-4-(1-naphthyl)-2-methyl-5-oxoquinoline-3-carboxylate
• 英文别名: ethyl 4-(2-methoxynaphthalen-1-yl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；Ethyl 2-methyl-4-(naphthalen-1-yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；ethyl 2-methyl-4-naphthalen-1-yl-5-oxo-4,6,7,8-tetrahydro-1H-quinoline-3-carboxylate
• CAS: 299451-82-4
• 化学式: C₂₃H₂₃NO₃
• 分子量: 361.441
• InChiKey: LFWNGSRUVVXXPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 1,3-环己二酮 、 1-萘甲醛 在 Cu(OTf)2 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以92%的产率得到ethyl 1,4,5,6,7,8-hexahydro-4-(1-naphthyl)-2-methyl-5-oxoquinoline-3-carboxylate
  参考文献：
  名称：

  Microwave-Assisted Copper(II)-Catalyzed One-Pot Four-Component Synthesis of Multifunctionalized Dihydropyridines

  摘要：

  A fast and highly efficient copper-catalyzed multicomponent synthesis of 1,4-dihydropyridines under microwave irradiation is described. The protocol utilizes mild reaction conditions with low catalytic loading, leading to high yields. This methodology provides us with biologically active 1,4-dihydropyridine library for medicinal chemistry applications.

  DOI：

  10.1021/cc100060s

文献信息

• Nafion-H®-catalyzed synthesis of polyhydroquinolines via the Hantzsch multicomponent reaction
  作者：Mazaahir Kidwai、Ritika Chauhan、Divya Bhatnagar、Abhay K. Singh、Biswajit Mishra、Sharmistha Dey

  DOI：10.1007/s00706-012-0742-4

  日期：2012.12

  A facile and efficient one-pot, four-component synthesis of polyhydroquinoline derivatives via the Hantzsch reaction using Nafion-H-A (R) as heterogeneous catalyst in PEG 400-water solvent system is described herein. The present methodology offers several advantages such as excellent yields, simple procedure, shorter reaction times, and milder conditions with remarkable recyclability.
• Microwave-Assisted Copper(II)-Catalyzed One-Pot Four-Component Synthesis of Multifunctionalized Dihydropyridines
  作者：Kalyan Kumar Pasunooti、Chantel Nixon Jensen、Hua Chai、Min Li Leow、Da-Wei Zhang、Xue-Wei Liu

  DOI：10.1021/cc100060s

  日期：2010.7.12

  A fast and highly efficient copper-catalyzed multicomponent synthesis of 1,4-dihydropyridines under microwave irradiation is described. The protocol utilizes mild reaction conditions with low catalytic loading, leading to high yields. This methodology provides us with biologically active 1,4-dihydropyridine library for medicinal chemistry applications.