N-(quinolin-8-yl)-[1,1′:3′,1″-terphenyl]-2′-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(quinolin-8-yl)-[1,1′:3′,1″-terphenyl]-2′-carboxamide
• 英文别名: N-(quinolin-8-yl)-[1,1':3',1''-terphenyl]-2'-carboxamide；2,6-diphenyl-N-quinolin-8-ylbenzamide
• 化学式: C₂₈H₂₀N₂O
• 分子量: 400.48
• InChiKey: XJBRCFTZTXYOMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  31
• 可旋转键数：
  4
• 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：

  2-苯基苯甲酰氯 在 potassium fluoride 、 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 2.0h， 生成 N-(quinolin-8-yl)-[1,1′:3′,1″-terphenyl]-2′-carboxamide
  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

• Step economical synthesis of o-aryl benzamides via C–H activation relayed by the in situ installation of directing group: a multicomponent method
  作者：Yunyun Liu、Yi Zhang、Meiying Huang、Jie-Ping Wan

  DOI：10.1039/c5ra09078d

  日期：——

  Multicomponent reactions have been successfully applied as a platform for the step economical C–H activation based synthesis wherein the in situ installation of directing group and the subsequent C–H arylation have been achieved in one-step.

  多组分反应已成功应用作为基于步骤经济的C-H活化合成的平台，在其中指导基团的原位安装和随后的C-H芳基化已在一步中实现。
• One-pot, solvent-free Pd(II)-catalyzed direct β-C-H arylation of carboxamides involving anhydrides as substrates via in situ installation of directing group
  作者：Arup Dalal、Prabhakar Singh、Srinivasarao Arulananda Babu

  DOI：10.1016/j.tet.2019.01.042

  日期：2019.3

  A one-pot, multicomponent-type, solvent-free Pd(II)-catalyzed direct beta-C-H activation/arylation of carboxamides involving anhydrides as substrates via in situ installation of directing group (DG) is reported. Typically, the DG-assisted beta-C-H activation/arylation of carboxamides is a two-step process comprising the installation of DG and Pd(II)-catalyzed C-H arylation. We attempted a multicomponent-type reaction comprising an anhydride, a DG (e.g. 8-aminoquinoline), an aryl iodide in the presence of the Pd(II) catalyst and an appropriate additive. Different anhydrides, DGs, aryl iodides, catalysts and additives were screened to reveal the scope of this multicomponent-type C-H arylation reaction process and various beta-C-H arylated carboxamides were obtained in satisfactory to good yields. (C) 2019 Elsevier Ltd. All rights reserved.
• 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.