1,4-dihydro-N,1-dimethyl-4-oxo-3-quinolinecarboxamide | 23910-12-5

• 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: 1,4-dihydro-N,1-dimethyl-4-oxo-3-quinolinecarboxamide
• 英文别名: N,1-dimethyl-4-oxoquinoline-3-carboxamide
• CAS: 23910-12-5
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: YMPPSNXXEOIRQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-chlorophenyl 2,4-dimethoxypyrimidin-5-yl ketone 在 四丙基氯化铵 、 palladium diacetate 、 potassium carbonate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以17%的产率得到1,4-dihydro-N,1-dimethyl-4-oxo-3-quinolinecarboxamide
  参考文献：
  名称：

  Synthesis of azafluorenones and related compounds using deprotocupration–aroylation followed by intramolecular direct arylation

  摘要：

  The efficiency of the deprotocupration-aroylation of 2-chloropyridine using lithiocuprates prepared from CuX (X=Cl, Br) and LiTMP (TMP=2,2,6,6-tetramethylpiperidido, 2 equiv) was investigated. CuCl was identified as a more suitable copper source than CuBr for this purpose. Different diaryl ketones bearing a halogen at the 2 position of one of the aryl groups were synthesized in this way from azines and thiophenes. These were then involved in palladium-catalyzed ring closure: substrates underwent expected CH-activation-type arylation to afford fluorenone-type compounds, and were also subjected to cyclization reactions leading to xanthones, notably in the presence of oxygen-containing substituents or reagents. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.030

文献信息

• DIHYDROQUINOLINONE COMPOUNDS AS MODULATORS OF THE MUSCARININC M1 RECEPTOR
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2821401B1

  公开（公告）日：2020-09-09
• Quinolinones, process for their preparation and pharmaceutical compositions containing them
  申请人：The Boots Company PLC

  公开号：EP0172004B1

  公开（公告）日：1990-03-21
• US4855291A
  申请人：——

  公开号：US4855291A

  公开（公告）日：1989-08-08
• Synthesis of azafluorenones and related compounds using deprotocupration–aroylation followed by intramolecular direct arylation
  作者：Nada Marquise、Philip J. Harford、Floris Chevallier、Thierry Roisnel、Vincent Dorcet、Anne-Laure Gagez、Sophie Sablé、Laurent Picot、Valérie Thiéry、Andrew E.H. Wheatley、Philippe C. Gros、Florence Mongin

  DOI：10.1016/j.tet.2013.09.030

  日期：2013.11

  The efficiency of the deprotocupration-aroylation of 2-chloropyridine using lithiocuprates prepared from CuX (X=Cl, Br) and LiTMP (TMP=2,2,6,6-tetramethylpiperidido, 2 equiv) was investigated. CuCl was identified as a more suitable copper source than CuBr for this purpose. Different diaryl ketones bearing a halogen at the 2 position of one of the aryl groups were synthesized in this way from azines and thiophenes. These were then involved in palladium-catalyzed ring closure: substrates underwent expected CH-activation-type arylation to afford fluorenone-type compounds, and were also subjected to cyclization reactions leading to xanthones, notably in the presence of oxygen-containing substituents or reagents. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.