D-N-(naphthalen-1-yl)quinoline-2-carboxamide | 1423074-17-2

• 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: D-N-(naphthalen-1-yl)quinoline-2-carboxamide
• 英文别名: N-(8-deuterionaphthalen-1-yl)quinoline-2-carboxamide
• CAS: 1423074-17-2
• 化学式: C₂₀H₁₄N₂O
• 分子量: 299.336
• InChiKey: OQPQWJMVVLFRNQ-QOWOAITPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• 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：
  2

反应信息

• 作为反应物：
  描述：

  D-N-(naphthalen-1-yl)quinoline-2-carboxamide 、 重氮乙酸甲酯 在 palladium diacetate 、 Potassium benzoate 作用下， 以 neat (no solvent) 为溶剂， 以69 %的产率得到methyl 2-((8-quinoline-2-carboxamido)naphthalen-1-yl)acetate
  参考文献：
  名称：

  协同可见光和 Pd 催化的 1-萘胺与 α-重氮酯的 C-H 烷基化

  摘要：

  可见光照射和 Pd 催化的结合已实际用于萘胺和 α-重氮酯的 C-H 烷基化反应，导致在温和反应条件下通过 C-C 键构建合成 α-萘基官能化乙酸酯和在无溶剂条件下。光照射已被证明在反应中起着关键作用，可能是通过促进 α-重氮酯生成活性卡宾物种。

  DOI：

  10.1021/acs.joc.2c01702
• 作为产物：
  描述：

  N-(naphthalen-1-yl)quinoline-2-carboxamide 在 重水 、 palladium diacetate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 12.0h， 以94%的产率得到D-N-(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.
• Synergistic Visible Light and Pd-Catalyzed C–H Alkylation of 1-Naphthylamines with α-Diazoesters
  作者：Baoli Zhao、Haifeng Li、Fengxuan Jiang、Jie-Ping Wan、Kai Cheng、Yunyun Liu

  DOI：10.1021/acs.joc.2c01702

  日期：2023.1.6

  The combination of visible light irradiation and Pd-catalysis has been practically employed for the C–H alkylation reactions of naphthylamines and α-diazo esters, leading to the synthesis of α-naphthyl functionalized acetates via C–C bond construction under mild reaction conditions and under solvent-free conditions. The light irradiation has been proven to play a pivotal role in the reactions, probably

  可见光照射和 Pd 催化的结合已实际用于萘胺和 α-重氮酯的 C-H 烷基化反应，导致在温和反应条件下通过 C-C 键构建合成 α-萘基官能化乙酸酯和在无溶剂条件下。光照射已被证明在反应中起着关键作用，可能是通过促进 α-重氮酯生成活性卡宾物种。