N-(quinolin-8-yl)-2-(N-morpholino)-4-bromobenzamide | 1531629-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: N-(quinolin-8-yl)-2-(N-morpholino)-4-bromobenzamide
• 英文别名: 4-bromo-2-morpholino-N-(quinolin-8-yl)benzamide
• CAS: 1531629-08-9
• 化学式: C₂₀H₁₈BrN₃O₂
• 分子量: 412.286
• InChiKey: GFQORADPWBZXSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.46
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  吗啉 、 4-bromo-N-quinolin-8-ylbenzamide 在 碳酸氢钠 、 silver carbonate 、 cobalt acetylacetonate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 10.0h， 以62%的产率得到N-(quinolin-8-yl)-2-(N-morpholino)-4-bromobenzamide
  参考文献：
  名称：

  通过双齿螯合辅助的钴催化芳烃与烷基胺的直接胺化

  摘要：

  通过sp 2 C-H键官能化，借助于8-氨基喹啉作为辅助剂，用烷基胺对芳烃进行钴催化的CH-H胺化反应。该协议的吸引人的特征包括钴催化剂的低负载量和易于获得的试剂。

  DOI：

  10.1002/adsc.201600282

文献信息

• Copper-Catalyzed Intermolecular C(sp²)–H Amination with Electrophilic <i>O</i>-Benzoyl Hydroxylamines
  作者：Wei-Hao Rao、Qi Li、Li-Li Jiang、Xue-Wan Deng、Pan Xu、Fang-Yuan Chen、Ming Li、Guo-Dong Zou

  DOI：10.1021/acs.joc.1c01229

  日期：2021.8.6

  A copper-catalyzed intermolecular electrophilic amination of benzamides with O-benzoyl hydroxylamines was achieved with the assistance of an 8-aminoquinolyl group. With this protocol, good compatibility was observed for a variety of aryl amides and heteroaryl amides, and excellent tolerance with various functional groups was achieved. Significantly, the monoaminated product was overwhelmingly delivered

  在8-氨基喹啉基团的帮助下，铜催化的苯甲酰胺与O-苯甲酰羟胺的分子间亲电胺化作用得以实现。使用该方案，观察到各种芳基酰胺和杂芳基酰胺具有良好的相容性，并实现了对各种官能团的出色耐受性。值得注意的是，单胺化产物在简单的反应条件下被绝大多数交付。初步的机理研究表明，应该排除自由基途径，并且 C-H 活化可能是决定速率的步骤。
• Cobalt(II)-Catalyzed Electrooxidative C–H Amination of Arenes with Alkylamines
  作者：Xinlong Gao、Pan Wang、Li Zeng、Shan Tang、Aiwen Lei

  DOI：10.1021/jacs.7b13049

  日期：2018.3.28

  An environmentally friendly electrochemical protocol about cobalt-catalyzed C-H amination of arenes has been developed, which offers a simple way to access synthetically useful arylamines. In divided cells, a wide variety of arenes and alkylamines are examined to afford C-N formation products without using external oxidants, which avoids the formation of undesired byproducts and exhibits high atom

  已经开发了一种关于芳烃的钴催化 CH 胺化的环保电化学协议，它提供了一种简单的方法来获得合成有用的芳胺。在分开的电池中，检查了多种芳烃和烷基胺，以在不使用外部氧化剂的情况下提供 CN 形成产物，这避免了不需要的副产物的形成并表现出高原子经济性。重要的是，该反应还可以以中等效率扩展到克级。KIE 实验表明在限速步骤中可能不涉及 CH 键的裂解。
• Nickel-Catalyzed Direct Amination of Arenes with Alkylamines
  作者：Qiangqiang Yan、Zhengkai Chen、Wenlong Yu、Hong Yin、Zhanxiang Liu、Yuhong Zhang

  DOI：10.1021/acs.orglett.5b00990

  日期：2015.5.15

  The efficient nickel-catalyzed direct amination of arenes with simple alkylamines has been achieved with the assistance of a bidentate directing group through sp(2) C-H bond functionalization. Preliminary mechanistic investigations indicate that the reaction probably proceeds through a Ni-I/Ni-III catalytic pathway.
• Synthesis of Anthranilic Acid Derivatives through Iron-Catalyzed Ortho Amination of Aromatic Carboxamides with <i>N</i>-Chloroamines
  作者：Tatsuaki Matsubara、Sobi Asako、Laurean Ilies、Eiichi Nakamura

  DOI：10.1021/ja412521k

  日期：2014.1.15

  Arenes possessing an 8-quinolinylamide group as a directing group are ortho aminated with N-chloroamines and N-benzoyloxyamines in the presence of an iron/diphosphine catalyst and an organometallic base to produce anthranilic acid derivatives in high yield. The reaction proceeds via iron-catalyzed C H activation, followed by the reaction of the resulting iron intermediate with N-chloroamine. The choice of the directing group and diphosphine ligand is crucial for obtaining the anthranilic acid derivative with high yield and product selectivity.