2-phenyl-N-(quinolin-8-yl)-1-naphthamide | 1436849-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-phenyl-N-(quinolin-8-yl)-1-naphthamide
• 英文别名: 2-phenyl-N-quinolin-8-ylnaphthalene-1-carboxamide
• CAS: 1436849-27-2
• 化学式: C₂₆H₁₈N₂O
• 分子量: 374.442
• InChiKey: OLMFIWWHFDYVBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 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：
  2

反应信息

• 作为产物：
  描述：

  1-萘甲酸 在 potassium fluoride 、 氯化亚砜 、 palladium diacetate 、 特戊酸钠 、 三乙胺 、 对苯醌 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 2-phenyl-N-(quinolin-8-yl)-1-naphthamide
  参考文献：
  名称：

  通过定向 C-H 活化进行 Aryne 多组分反应

  摘要：

  许多研究人员最近探索了在导向基团的帮助下通过邻位 CH 活化的芳基化。在此，开发了一种使用 8-氨基喹啉作为双齿导向基团的钯催化的 C-H 芳基化反应。该反应仅提供 CH 芳基化，与观察到相应异喹诺酮环化的先前方法不同。更有趣的是，当加入丙烯酸甲酯和丙烯腈时，观察到连续的 CH 官能化；这导致与芳基的 CH 烯化，芳基由芳烃前体安装。

  DOI：

  10.1002/chem.202100205

文献信息

• Ruthenium-catalyzed direct arylation of C–H bonds in aromatic amides containing a bidentate directing group: significant electronic effects on arylation
  作者：Yoshinori Aihara、Naoto Chatani

  DOI：10.1039/c2sc21506c

  日期：——

  by a ruthenium-catalyzed reaction of aromatic amides having an 8-aminoquinoline moiety with aryl bromides. The reaction shows high functional group compatibility. The reaction proceeds in a highly selective manner at the less hindered C–H bonds of meta-substituted aromatic amides. Significant electronic effects are observed in Hammett plots. Electron-withdrawing groups on the aromatic amides facilitate

  的芳基化邻C-H键由具有与芳基溴化物的8-氨基喹啉基部分的芳族酰胺的钌催化反应来实现。该反应显示出高官能团相容性。该反应以较高选择性的方式在间位取代的芳族酰胺的C–H键受阻较小的位置进行。在Hammett图中观察到了明显的电子效应。芳族酰胺上的吸电子基团促进了反应。相反，芳基溴化物上的给电子基团和吸电子基团都加速了反应。
• Nickel(II)-Catalyzed Direct Arylation of C–H Bonds in Aromatic Amides Containing an 8-Aminoquinoline Moiety as a Directing Group
  作者：Ayana Yokota、Yoshinori Aihara、Naoto Chatani

  DOI：10.1021/jo501697n

  日期：2014.12.19

  Arylation via the cleavage of the ortho CH bonds by a nickel-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety with aryl iodides is reported. The reaction shows a high functional group compatibility. The reaction proceeds in a highly selective manner at the less hindered CH bonds in the reaction of meta-substituted aromatic amides, irrespective of the electronic nature of the substituents. Electron-withdrawing groups on the aromatic amides facilitate the reaction. Various mechanistic experiments, such as deuterium labeling experiments, Hammett studies, competition experiments, and radical trap experiments, have been made for better understanding the reaction mechanism. It is found that the cleavage of CH bonds is reversible on the basis of the deuterium labeling experiments. Both Ni(II) and Ni(0) show a high catalytic activity, but the results of mechanistic experiments suggest that a Ni(0)/Ni(II) catalytic cycle is not involved.
• Aryne Multicomponent Reactions by Directed C−H Activation
  作者：Sunil Kumar Sunnam、Jitendra D. Belani

  DOI：10.1002/chem.202100205

  日期：2021.6.16

  Arylation via ortho C−H activation by the aid of directing groups has been explored recently by many researchers. Herein, a palladium-catalyzed C−H arylation using 8-aminoquinoline as a bidentate directing group has been developed. The reaction furnishes only C−H arylation, unlike previous methods where cyclization to corresponding isoquinolones is observed. More interestingly, sequential C−H functionalization

  许多研究人员最近探索了在导向基团的帮助下通过邻位 CH 活化的芳基化。在此，开发了一种使用 8-氨基喹啉作为双齿导向基团的钯催化的 C-H 芳基化反应。该反应仅提供 CH 芳基化，与观察到相应异喹诺酮环化的先前方法不同。更有趣的是，当加入丙烯酸甲酯和丙烯腈时，观察到连续的 CH 官能化；这导致与芳基的 CH 烯化，芳基由芳烃前体安装。