7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxylic acid

• 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: 7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 7-Chloro-1,4-dihydro-4-oxo-1-phenyl-3-quinolinecarboxylic acid；7-Chloro-1,4-dihydro-4-oxo-1-phenyl3-quinolinecarboxylic acid；7-chloro-4-oxo-1-phenylquinoline-3-carboxylic acid
• 化学式: C₁₆H₁₀ClNO₃
• 分子量: 299.713
• InChiKey: AHPCHXJEARRGOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-溴-2H-苯并吡喃-2-酮 、 7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxylic acid 在 silver carbonate 、 双(2-二苯基磷苯基)醚 、 palladium(II) bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以68%的产率得到7-chloro-3-(2-oxo-2H-chromen-3-yl)-1-phenylquinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis of Biheterocycles Based on Quinolinone, Chromone, and Coumarin Scaffolds by Palladium-Catalyzed Decarboxylative Couplings

  摘要：

  An efficient Pd-catalyzed decarboxylative coupling of heterocyclic carboxylic acids with heterocyclic halides to achieve the synthesis of biheterocycles of biological interest has been reported. In all cases, the cross-coupling reactions take place rapidly in DMSO in good yields and efficiently proceed in the presence of a PdBr2/DPEphos catalytic system, furnishing the novel biheterocycles based on quinolin-4-one, quinolin-2-one, chromone, and coumarin scaffolds.

  DOI：

  10.1021/acs.joc.5b02103
• 作为产物：
  描述：

  Ethyl 7-chloro-1,4-dihydro-4-oxo-1-phenyl-3-quinolinecarboxylate 、 sodium hydroxide 、 四氢呋喃 生成 7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  WENTLAND, MARK P.

  摘要：

  DOI：

文献信息

• Quinolonecarboxamide compounds, their preparation and use as antivirals.
  申请人：Sterling Drug Inc.

  公开号：US04959363A1

  公开（公告）日：1990-09-25

  Compounds of the formula ##STR1## where R is hydrogen, hydroxy, amino or lwer-alkyl; R.sup.1 is lower-alkyl, lower-alkenyl, cycloalkyl, pyridinyl, phenyl or substituted phenyl; R.sup.2 is hydrogen, amino or hydroxy; R.sup.6 is hydrogen or fluoro; and R.sup.7 is phenyl, pyridinyl or selected other heterocycles, have antiviral acitivity against herpes virus. The compounds are prepared from the corresponding carboxylic acids or ester, or by a tin-coupling reaction on the corresponding 7-halo compounds.

  式子为##STR1##的化合物，其中R为氢、羟基、氨基或低碳基；R.sup.1为低碳基、低烯基、环烷基、吡啶基、苯基或取代苯基；R.sup.2为氢、氨基或羟基；R.sup.6为氢或氟；R.sup.7为苯基、吡啶基或其他选择的杂环基团，具有抗病毒活性，可用于对抗疱疹病毒。这些化合物可以通过相应的羧酸或酯制备，或通过对应的7-卤代化合物进行锡偶联反应制备。
• WENTLAND, MARK P.
  作者：WENTLAND, MARK P.

  DOI：——

  日期：——
• US4959363A
  申请人：——

  公开号：US4959363A

  公开（公告）日：1990-09-25
• Synthesis of Biheterocycles Based on Quinolinone, Chromone, and Coumarin Scaffolds by Palladium-Catalyzed Decarboxylative Couplings
  作者：K. Harsha Vardhan Reddy、Jean-Daniel Brion、Samir Messaoudi、Mouad Alami

  DOI：10.1021/acs.joc.5b02103

  日期：2016.1.15

  An efficient Pd-catalyzed decarboxylative coupling of heterocyclic carboxylic acids with heterocyclic halides to achieve the synthesis of biheterocycles of biological interest has been reported. In all cases, the cross-coupling reactions take place rapidly in DMSO in good yields and efficiently proceed in the presence of a PdBr2/DPEphos catalytic system, furnishing the novel biheterocycles based on quinolin-4-one, quinolin-2-one, chromone, and coumarin scaffolds.