N-(8-(3-fluorophenyl)naphthalen-1-yl)quinoline-2-carboxamide | 1423074-11-6

• 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: N-(8-(3-fluorophenyl)naphthalen-1-yl)quinoline-2-carboxamide
• 英文别名: N-[8-(3-fluorophenyl)naphthalen-1-yl]quinoline-2-carboxamide
• CAS: 1423074-11-6
• 化学式: C₂₆H₁₇FN₂O
• 分子量: 392.432
• InChiKey: SWHCSOBWZYLIBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  喹哪啶酸 在 potassium acetate 、 palladium diacetate 、 三乙胺 、 三氯氧磷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 反应 14.5h， 生成 N-(8-(3-fluorophenyl)naphthalen-1-yl)quinoline-2-carboxamide
  参考文献：
  名称：

  Palladium(II)-Catalyzed Regioselective Arylation of Naphthylamides with Aryl Iodides Utilizing a Quinolinamide Bidentate System

  摘要：

  A palladium(II)-catalyzed quinolinamide-directed 8-arylation of 1-naphthylamides with aryl iodides is reported. The bidentate directing group (quinolinamide) proved to be crucial for a highly regioselective transformation. In addition, the amide directing group can be easily hydrolyzed under basic conditions to offer a range of 8-aryl-1-naphthylamine derivatives. The theoretical calculations suggest that the C-H arylation reaction proceeds through a sequential C-H activation/oxidative addition pathway.

  DOI：

  10.1021/jo400017v

文献信息

• Palladium(II)-Catalyzed Regioselective Arylation of Naphthylamides with Aryl Iodides Utilizing a Quinolinamide Bidentate System
  作者：Lehao Huang、Qian Li、Chen Wang、Chenze Qi

  DOI：10.1021/jo400017v

  日期：2013.4.5

  A palladium(II)-catalyzed quinolinamide-directed 8-arylation of 1-naphthylamides with aryl iodides is reported. The bidentate directing group (quinolinamide) proved to be crucial for a highly regioselective transformation. In addition, the amide directing group can be easily hydrolyzed under basic conditions to offer a range of 8-aryl-1-naphthylamine derivatives. The theoretical calculations suggest that the C-H arylation reaction proceeds through a sequential C-H activation/oxidative addition pathway.