2-hydroxy-N-(quinolin-8-yl)benzamide | 312503-18-7

• 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
• 英文名称: 2-hydroxy-N-(quinolin-8-yl)benzamide
• 英文别名: Cambridge id 6811921；2-hydroxy-N-quinolin-8-ylbenzamide
• CAS: 312503-18-7
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: JKKTYFPZJYHZLU-UHFFFAOYSA-N

物化性质

• 沸点：
  400.7±25.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-N-(quinolin-8-yl)benzamide 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以73%的产率得到水杨酸
  参考文献：
  名称：

  Divergent copper-mediated dimerization and hydroxylation of benzamides involving C–H bond functionalization

  摘要：

  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。

  DOI：

  10.1039/c6ob00392c
• 作为产物：
  描述：

  2-methoxy-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 12.0h， 以56%的产率得到2-hydroxy-N-(quinolin-8-yl)benzamide
  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

• Copper(II)-Mediated Intermolecular C(sp²)–H Amination of Benzamides with Electron-Rich Anilines
  作者：Bijaya Kumar Singh、Arghya Polley、Ranjan Jana

  DOI：10.1021/acs.joc.6b00659

  日期：2016.5.20

  catalyst deactivation and deleterious side reactions. Herein, we report a copper(II)-mediated C(sp2)–H amination of benzamides with electronically neutral or electron-rich anilines. A dramatic influence of silver(I) and tetrabutylammonium bromide was observed on the reaction outcome. The present protocol also demonstrates the synthesis of a number of nonsteroidal anti-inflammatory drugs.

  尽管取得了重大进展，但由于催化剂失活和有害的副反应，铜催化/介导的CH-H与富电子苯胺的胺化反应仍未解决。在这里，我们报告了苯甲酰胺与电子中性或富电子苯胺的铜（II）介导的C（sp 2）–H胺化。观察到银（I）和溴化四丁铵对反应结果的显着影响。本方案还证明了许多非甾体抗炎药的合成。
• Copper-Catalyzed Direct Acyloxylation of C(sp²)–H Bonds in Aromatic Amides
  作者：Feifan Wang、Qiyan Hu、Chao Shu、Zhiyang Lin、Dewen Min、Tianchao Shi、Wu Zhang

  DOI：10.1021/acs.orglett.7b01559

  日期：2017.7.7

  Copper-catalyzed ortho-acyloxylation of the sp2 C–H bond of aryl amides with carboxylic acids is reported. Benzoic acids, cinnamic acids, and aliphatic acids can be involved, and the desired products were obtained in moderate to good yields. This procedure is compatible with a wide range of functional groups and heteroarenes without the use of any ligands or additives. This method provides an operationally

  据报道，铜催化芳基酰胺的sp 2 C–H键与羧酸发生邻位酰氧基化反应。可以涉及苯甲酸，肉桂酸和脂族酸，并且以中等至良好的产率获得了所需的产物。该方法无需使用任何配体或添加剂即可与各种官能团和杂芳烃兼容。该方法为合成苯甲酸酯和肉桂酸酯提供了一种操作简单的方法。
• Copper-Mediated Hydroxylation of Arenes and Heteroarenes Directed by a Removable Bidentate Auxiliary
  作者：Xin Li、Yan-Hua Liu、Wen-Jia Gu、Bo Li、Fa-Jie Chen、Bing-Feng Shi

  DOI：10.1021/ol5016064

  日期：2014.8.1

  A copper-mediated C-H hydroxylation of arenes and heteroarenes using our newly developed PIP directing group has been developed. This procedure is scalable and compatible with a wide range of functional groups and heteroarenes, providing an operationally simple protocol for the synthesis of o-hydroxybenzamides. The hydroxylation of nicotinamides gave 4-oxo-1,4-dihydropyridine-3-carboxamides selectively. Preliminary mechanistic studies implicate that a basic ligand-enabled, irreversible, rate-determining CMD step is most likely involved in this process.
• Copper-/Silver-Mediated Arylation of C(sp²)–H Bonds with 2-Thiophenecarboxylic Acids
  作者：Sheng Zhao、Yue-Jin Liu、Sheng-Yi Yan、Fa-Jie Chen、Zhuo-Zhuo Zhang、Bing-Feng Shi

  DOI：10.1021/acs.orglett.5b01560

  日期：2015.7.2

  A copper/silver-mediated arylation of (hetero)aryl C-H bonds with 2-thiophenecarboxylic acids has been achieved. The protocol features a broad substrate scope and high functional group tolerance. Preliminary mechanistic studies indicate that a cascade protodecarboxylation/dehydrogenative coupling process is likely involved.
• 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。