2-(4-chloro-phenyl)-1-phenylquinolin-4(1H)-one | 1203669-38-8

• 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: 2-(4-chloro-phenyl)-1-phenylquinolin-4(1H)-one
• 英文别名: ZTK-1-308；2-(4-Chlorophenyl)-1-phenylquinolin-4-one；2-(4-chlorophenyl)-1-phenylquinolin-4-one
• CAS: 1203669-38-8
• 化学式: C₂₁H₁₄ClNO
• 分子量: 331.801
• InChiKey: XLLQEZMVABTWNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 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：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(2-溴苯基)-3-(4-氯苯基)丙-2-炔-1-酮 、 苯胺 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 potassium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 7.0h， 以63%的产率得到2-(4-chloro-phenyl)-1-phenylquinolin-4(1H)-one
  参考文献：
  名称：

  Palladium-Catalyzed Tandem Amination Reaction for the Synthesis of 4-Quinolones

  摘要：

  An efficient palladium-catalyzed tandem amination approach was developed In one step to afford functionalized 4-quinolones In good to excellent yields from easily accessible o-haloaryl acetylenic ketones and primary amines.

  DOI：

  10.1021/ol902626d

文献信息

• Direct Synthesis of 4-Quinolones via Copper-Catalyzed Anilines and Alkynes
  作者：Xuefeng Xu、Xu Zhang

  DOI：10.1021/acs.orglett.7b02495

  日期：2017.9.15

  and direct approach for constructing 4-quinolones from simple and readily available anilines and alkynes is described. Under the optimal conditions, both N-alkyl- and N-aryl-substituted anilines can be successfully transformed into the corresponding 4-quinolones. This reaction is characterized by mild reaction conditions, high functional-group tolerance, and amenability to gram-scale synthesis.

  描述了一种从简单易得的苯胺和炔烃构建4-喹诺酮的独特直接方法。在最佳条件下，N-烷基-和N-芳基取代的苯胺均可成功转化为相应的4-喹诺酮。该反应的特征在于温和的反应条件，高官能团耐受性和对克级合成的适应性。
• Buchwald-Hartwig Coupling/Michael Addition Reactions: One-Pot Synthesis of 1,2-Disubstituted 4-Quinolones from Chalcones and Primary Amines
  作者：Xiang-Dong Fei、Zhou Zhou、Wen Li、Yong-Ming Zhu、Jing-Kang Shen

  DOI：10.1002/ejoc.201200172

  日期：2012.5

  The Buchwald–Hartwig coupling/Michael addition sequence has been successfully applied to the synthesis of functionalized 1,2-disubstituted 4-quinolones using Pd(OAc)2 as a catalyst and PPh3 as a ligand. Under these conditions, the intermediate products first formed from chalcones and primary amines underwent catalytic dehydrogenation to yield the 1,2-disubstituted 4-quinolones.

  Buchwald-Hartwig 偶联/迈克尔加成序列已成功应用于使用 Pd(OAc)2 作为催化剂和 PPh3 作为配体的功能化 1,2-二取代 4-喹诺酮类化合物的合成。在这些条件下，首先由查耳酮和伯胺形成的中间产物经过催化脱氢生成 1,2-二取代的 4-喹诺酮。
• Palladium-Catalyzed Tandem Amination Reaction for the Synthesis of 4-Quinolones
  作者：Tiankun Zhao、Bin Xu

  DOI：10.1021/ol902626d

  日期：2010.1.15

  An efficient palladium-catalyzed tandem amination approach was developed In one step to afford functionalized 4-quinolones In good to excellent yields from easily accessible o-haloaryl acetylenic ketones and primary amines.