3-(naphthalene-2-carbonyl)-1,4-dihydroquinolin-4-one | 821004-10-8

• 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: 3-(naphthalene-2-carbonyl)-1,4-dihydroquinolin-4-one
• 英文别名: 3-(2-Naphthoyl)quinolin-4(1H)-one；3-(naphthalene-2-carbonyl)-1H-quinolin-4-one
• CAS: 821004-10-8
• 化学式: C₂₀H₁₃NO₂
• 分子量: 299.329
• InChiKey: MQJXYXBBQAYJAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-溴戊烷 、 3-(naphthalene-2-carbonyl)-1,4-dihydroquinolin-4-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以40%的产率得到3-(Naphthalene-2-carbonyl)-1-pentyl-1,4-dihydroquinolin-4-one
  参考文献：
  名称：

  Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands:  Consequences in Receptor Affinity and Functionality

  摘要：

  CB2 receptor selective ligands are becoming increasingly attractive drugs due to the potential role of this receptor in several physiopathological processes. Thus, the development of our previously described series of 4-oxo- 1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further characterize the structure-affinity and structure - functionality relationships of these derivatives. The influence of the side chain was investigated by synthesizing compounds bearing various carboxamido and keto substituents. On the other hand, the role of the quinoline central scaffold was studied by synthesizing several 6-, 7-, or 8-chloro-4oxo-1,4-dihydroquinolines, as well as 4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The effect of these modifications on the affinity and functionality at the CB2 receptor was studied and allowed for the characterization of new selective CB2 receptor ligands.

  DOI：

  10.1021/jm070387h
• 作为产物：
  描述：

  (E)-3-ethoxy-1-(2-naphthyl)propenone 在 sodium methylate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二苯醚 为溶剂， 反应 28.25h， 生成 3-(naphthalene-2-carbonyl)-1,4-dihydroquinolin-4-one
  参考文献：
  名称：

  A versatile and efficient synthesis of 3-aroyl-1,4-dihydroquinolin-4-ones

  摘要：

  A versatile and efficient method for preparation of 3-aroyl-4-quinolones is described. The procedure involved a Michael-type addition of methyl anthranylate with various beta-ketonic enol ethers followed by based promoted cyclisation. Different quinolones have been obtained. The ring closure is facilitated by heating at reflux in diphenyl ether leading to increase the rate of the cyclisation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.067

文献信息

• Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB₂-Selective Cannabinoid Receptor Ligands:  Consequences in Receptor Affinity and Functionality
  作者：Eric Stern、Giulio G. Muccioli、Barbara Bosier、Laurie Hamtiaux、Régis Millet、Jacques H. Poupaert、Jean-Pierre Hénichart、Patrick Depreux、Jean-François Goossens、Didier M. Lambert

  DOI：10.1021/jm070387h

  日期：2007.11.1

  CB2 receptor selective ligands are becoming increasingly attractive drugs due to the potential role of this receptor in several physiopathological processes. Thus, the development of our previously described series of 4-oxo- 1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further characterize the structure-affinity and structure - functionality relationships of these derivatives. The influence of the side chain was investigated by synthesizing compounds bearing various carboxamido and keto substituents. On the other hand, the role of the quinoline central scaffold was studied by synthesizing several 6-, 7-, or 8-chloro-4oxo-1,4-dihydroquinolines, as well as 4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The effect of these modifications on the affinity and functionality at the CB2 receptor was studied and allowed for the characterization of new selective CB2 receptor ligands.
• A versatile and efficient synthesis of 3-aroyl-1,4-dihydroquinolin-4-ones
  作者：Eric Stern、Régis Millet、Patrick Depreux、Jean-Pierre Hénichart

  DOI：10.1016/j.tetlet.2004.10.067

  日期：2004.12

  A versatile and efficient method for preparation of 3-aroyl-4-quinolones is described. The procedure involved a Michael-type addition of methyl anthranylate with various beta-ketonic enol ethers followed by based promoted cyclisation. Different quinolones have been obtained. The ring closure is facilitated by heating at reflux in diphenyl ether leading to increase the rate of the cyclisation. (C) 2004 Elsevier Ltd. All rights reserved.