6-fluoro-1-methyl-3,4-diphenylquinolin-2(1H)-one | 1185649-71-1

• 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-fluoro-1-methyl-3,4-diphenylquinolin-2(1H)-one
• 英文别名: 6-Fluoro-1-methyl-3,4-diphenylquinolin-2-one
• CAS: 1185649-71-1
• 化学式: C₂₂H₁₆FNO
• 分子量: 329.374
• InChiKey: LPQSBJHZXLLYRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  N-(4-fluorophenyl)-N-methyl-3-phenylpropiolamide 、 苯 、 三甲基乙酸 在 silver(I) acetate 、 palladium diacetate 、 三苯基膦 作用下， 反应 24.0h， 以51%的产率得到6-fluoro-1-methyl-3,4-diphenylquinolin-2(1H)-one
  参考文献：
  名称：

  Selective Synthesis of 3-Aryl Quinolin-2(1H)-ones and 3-(1-Arylmethylene)oxindoles Involving a 2-Fold Arene C−H Activation Process

  摘要：

  A novel and selective palladium-catalyzed C-H activation protocol has been developed for the synthesis of 3-aryl quinolin-2(1H)-ones and 3-(1-arylmethylene)oxindoles with use of PivOH as the switch. In the presence of Pd(OAc)(2), AgOAc, and PivOH, a variety or N-methyl anilides reacted with arenes to afford the corresponding 3-aryl quinolin-2(l H)-ones in moderate yields, whereas the selectivity was shifted toward 3-(1-arylmethylene)oxindoles in the absence of PivOH.

  DOI：

  10.1021/jo901314t

文献信息

• Selective Synthesis of 3-Aryl Quinolin-2(1<i>H</i>)-ones and 3-(1-Arylmethylene)oxindoles Involving a 2-Fold Arene C−H Activation Process
  作者：Dong-Jun Tang、Bo-Xiao Tang、Jin-Heng Li

  DOI：10.1021/jo901314t

  日期：2009.9.4

  A novel and selective palladium-catalyzed C-H activation protocol has been developed for the synthesis of 3-aryl quinolin-2(1H)-ones and 3-(1-arylmethylene)oxindoles with use of PivOH as the switch. In the presence of Pd(OAc)(2), AgOAc, and PivOH, a variety or N-methyl anilides reacted with arenes to afford the corresponding 3-aryl quinolin-2(l H)-ones in moderate yields, whereas the selectivity was shifted toward 3-(1-arylmethylene)oxindoles in the absence of PivOH.