N-(quinolin-8-yl)-2-(N-morpholino)-5-dimethylaminobenzamide | 1531629-10-3

• 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)-5-dimethylaminobenzamide
• 英文别名: 5-(dimethylamino)-2-morpholino-N-(quinolin-8-yl)benzamide；5-(dimethylamino)-2-morpholin-4-yl-N-quinolin-8-ylbenzamide
• CAS: 1531629-10-3
• 化学式: C₂₂H₂₄N₄O₂
• 分子量: 376.458
• InChiKey: WMLICBPTXZPEPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吗啉 、 3-(dimethylamino)-N-(quinolin-8-yl)benzamide 在 nickel diacetate 、 sodium carbonate 、 silver carbonate 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以75%的产率得到N-(quinolin-8-yl)-2-(N-morpholino)-5-dimethylaminobenzamide
  参考文献：
  名称：

  Nickel-Catalyzed Direct Amination of Arenes with Alkylamines

  摘要：

  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.

  DOI：

  10.1021/acs.orglett.5b00990

文献信息

• 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.