6-bromo-1-methyl-3-(trimethylsilylethynyl)quinolin-4(1H)-one | 1320361-59-8

• 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: 6-bromo-1-methyl-3-(trimethylsilylethynyl)quinolin-4(1H)-one
• 英文别名: 6-Bromo-1-methyl-3-(2-trimethylsilylethynyl)quinolin-4-one；6-bromo-1-methyl-3-(2-trimethylsilylethynyl)quinolin-4-one
• CAS: 1320361-59-8
• 化学式: C₁₅H₁₆BrNOSi
• 分子量: 334.288
• InChiKey: KZNDLFMFNMIPBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-bromo-1-methyl-3-(trimethylsilylethynyl)quinolin-4(1H)-one 、 4-氰基苯硼酸 在 palladium diacetate 、 sodium carbonate 、 三苯基膦 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 0.08h， 以44%的产率得到6-(4-cyanophenyl)-1-methyl-3-(trimethylsilylethynyl)quinolin-4(1H)-one
  参考文献：
  名称：

  Regioselective functionalization of quinolin-4(1H)-ones via sequential palladium-catalyzed reactions

  摘要：

  A practical and general synthesis of 1,3,6-trisubstituted quinolin-4(1H)-ones starting from 1-alkyl-6-bromo-3-iodoquinolin-4(1H)-one is described, based on regioselective sequential palladium-catalyzed cross-coupling reactions, namely Suzuki-Miyaura, Sonogashira and aminocarbonylation reactions, under microwave irradiation. Good substrate generality, ease of execution and practicability make this method exploitable for the generation of libraries of chemically diverse 4-quinolones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.134
• 作为产物：
  描述：

  ethyl-3-(4-bromoaniline)acrylate 在 bis-triphenylphosphine-palladium(II) chloride 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 potassium carbonate 、 二异丙胺 作用下， 以 1,4-二氧六环 、 二苯醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.3h， 生成 6-bromo-1-methyl-3-(trimethylsilylethynyl)quinolin-4(1H)-one
  参考文献：
  名称：

  Regioselective functionalization of quinolin-4(1H)-ones via sequential palladium-catalyzed reactions

  摘要：

  A practical and general synthesis of 1,3,6-trisubstituted quinolin-4(1H)-ones starting from 1-alkyl-6-bromo-3-iodoquinolin-4(1H)-one is described, based on regioselective sequential palladium-catalyzed cross-coupling reactions, namely Suzuki-Miyaura, Sonogashira and aminocarbonylation reactions, under microwave irradiation. Good substrate generality, ease of execution and practicability make this method exploitable for the generation of libraries of chemically diverse 4-quinolones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.134

文献信息

• Regioselective functionalization of quinolin-4(1H)-ones via sequential palladium-catalyzed reactions
  作者：Claudia Mugnaini、Chiara Falciani、Maria De Rosa、Antonella Brizzi、Serena Pasquini、Federico Corelli

  DOI：10.1016/j.tet.2011.05.134

  日期：2011.8

  A practical and general synthesis of 1,3,6-trisubstituted quinolin-4(1H)-ones starting from 1-alkyl-6-bromo-3-iodoquinolin-4(1H)-one is described, based on regioselective sequential palladium-catalyzed cross-coupling reactions, namely Suzuki-Miyaura, Sonogashira and aminocarbonylation reactions, under microwave irradiation. Good substrate generality, ease of execution and practicability make this method exploitable for the generation of libraries of chemically diverse 4-quinolones. (C) 2011 Elsevier Ltd. All rights reserved.