2-羟基-4-甲基-N-(喹啉-8-基)苯甲酰胺 | 1019379-21-5

• 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
• 中文名称: 2-羟基-4-甲基-N-(喹啉-8-基)苯甲酰胺
• 英文名称: 2-hydroxy-4-methyl-N-(quinolin-8-yl)benzamide
• 英文别名: 2-hydroxy-4-methyl-N-quinolin-8-ylbenzamide
• CAS: 1019379-21-5
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: LTMXGKBRSIUAKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-methyl-N-(quinolin-8-yl)benzamide 在 吡啶 、 copper(II) acetate monohydrate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以97%的产率得到2-羟基-4-甲基-N-(喹啉-8-基)苯甲酰胺
  参考文献：
  名称：

  配体使能，铜促进的芳烃，芳基卤化物和芳基甲基醚的区域和化学选择性羟基化

  摘要：

  我们在这里报告了一种便宜的乙酸铜（II）一水合物和吡啶配体对苯甲酰胺进行邻位C-H羟基化的实用方法。探索了分子内和分子间配体的组合以实现区域和化学选择性羟基化。有趣的是，通过引入卤代芳烃和芳基甲基醚的配体定向邻羟基化进一步解决了与C–H活化相关的典型区域化学加扰。

  DOI：

  10.1021/acs.joc.5b02302

文献信息

• Divergent copper-mediated dimerization and hydroxylation of benzamides involving C–H bond functionalization
  作者：Mingliang Wang、Yimin Hu、Zhe Jiang、Hong C. Shen、Xun Sun

  DOI：10.1039/c6ob00392c

  日期：——

  Copper-mediated C–H activation of aminoquinoline benzamides to give either hydroxylation or dimerization compounds were investigated.

  铜介导的氨基喹啉苯甲酰胺的C-H活化，可以得到羟基化或二聚化合物。
• Design, synthesis and biological evaluation of quinoline amide derivatives as novel VEGFR-2 inhibitors
  作者：Ying Yang、Lei Shi、Yang Zhou、Huan-Qiu Li、Zhen-Wei Zhu、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2010.09.014

  日期：2010.11

  Vascular endothelial growth factor receptor-2 (VEGFR-2) plays a crucial role in the process of cancer angiogenesis. A series of quinoline amide derivatives were prepared and found to be good inhibitors of VEGFR-2. The inhibitory activities were investigated against VEGFR-2 kinase and human umbilical vein endothelial cells (HUVEC) in vitro. Compound 6 (5-chloro-2-hydroxy-N-(quinolin-8-yl)benzamide) exhibited the most potent inhibitory activity (IC(50) = 3.8 and 5.5 nM for VEGFR-2 kinase and HUVEC, respectively). Docking simulation supported the initial pharmacophoric hypothesis and suggested a common mode of interaction at the ATP-binding site of VEGFR-2, which demonstrates that compound 6 is a potential agent for cancer therapy deserving further researching. (C) 2010 Elsevier Ltd. All rights reserved.
• Ligand-Enabled, Copper-Promoted Regio- and Chemoselective Hydroxylation of Arenes, Aryl Halides, and Aryl Methyl Ethers
  作者：Bijaya Kumar Singh、Ranjan Jana

  DOI：10.1021/acs.joc.5b02302

  日期：2016.2.5

  chemoselective hydroxylation. Interestingly, typical regiochemical scrambling associated with the C–H activation was further resolved by introducing a ligand-directed ortho hydroxylation of haloarenes and aryl methyl ethers.

  我们在这里报告了一种便宜的乙酸铜（II）一水合物和吡啶配体对苯甲酰胺进行邻位C-H羟基化的实用方法。探索了分子内和分子间配体的组合以实现区域和化学选择性羟基化。有趣的是，通过引入卤代芳烃和芳基甲基醚的配体定向邻羟基化进一步解决了与C–H活化相关的典型区域化学加扰。