N-phenyl-2-(pyridin-2-yl)benzamide | 1314147-45-9

• 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-phenyl-2-(pyridin-2-yl)benzamide
• 英文别名: N-phenyl-2-pyridin-2-ylbenzamide
• CAS: 1314147-45-9
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: MSEXCABQSSKUIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• 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：

  苯甲酰氯 在 silver hexafluoroantimonate 、 sodium azide 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 乙腈 作用下， 以 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 18.0h， 生成 N-phenyl-2-(pyridin-2-yl)benzamide
  参考文献：
  名称：

  Orthogonal Reactivity of Acyl Azides in C–H Activation: Dichotomy between C–C and C–N Amidations Based on Catalyst Systems

  摘要：

  The dual reactivity of acyl azides was utilized successfully in C-H activation by the choice of catalyst systems: while selective C-C amidation was achieved under thermal Rh catalysis, a Ru catalyst was found to mediate direct C-N amidation also highly selectively. Investigations of the mechanistic dichotomy between two catalytic systems are also presented.

  DOI：

  10.1021/ol500602b

文献信息

• RuHCl(CO)(PPh₃)₃-Catalyzed Direct Amidation of Arene C–H Bond with Azides
  作者：Xinsheng Xiao、Guokai Jia、Fang Liu、Guangchuan Ou、Ying Xie

  DOI：10.1021/acs.joc.8b02123

  日期：2018.11.16

  We first report the direct ortho C–H amidation of arenes with azides by using a novel and inexpensive RuHCl(CO)(PPh3)3 catalyst. The reaction proceeds efficiently in high yield over a broad range of substrates without requirement of any additional silver salt or additive.

  我们首先报道了使用新型廉价的RuHCl（CO）（PPh 3）3催化剂将芳烃与叠氮化物直接邻位H-H酰胺化反应。该反应可在广泛的底物上以高收率高效地进行，而无需任何其他的银盐或添加剂。
• Expedient Synthesis of <i>N</i>-Acyl Anthranilamides and β-Enamine Amides by the Rh(III)-Catalyzed Amidation of Aryl and Vinyl C–H Bonds with Isocyanates
  作者：Kevin D. Hesp、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/ja203495c

  日期：2011.8.3

  A Rh(III)-catalyzed protocol for the amidation of anilide and enamide C-H bonds with isocyanates has been developed. This method provides direct and efficient syntheses of N-acyl anthranilamides, enamine amides, and pyrimidin-4-one heterocycles.

  已经开发了一种用于将苯胺和烯酰胺 CH 键与异氰酸酯酰胺化的 Rh(III) 催化方案。该方法直接有效地合成了 N-酰基邻氨基苯甲酰胺、烯胺酰胺和嘧啶-4-一杂环。
• Pyridine-substituted benzanilides as potassium ion channel openers
  申请人：——

  公开号：US20010049444A1

  公开（公告）日：2001-12-06

  The present invention provides a genus of pyridine-substituted benzanilides that are useful as openers of potassium ion channels. The compounds of the invention are of use in both therapeutic and diagnostic methods.

  本发明提供了一类取代吡啶基苯甲酰苯胺的属，这些属可作为钾离子通道的开启剂。本发明的化合物在治疗和诊断方法中均有用途。
• Cobalt(III)-Catalyzed C–H Bond Amidation with Isocyanates
  作者：Joshua R. Hummel、Jonathan A. Ellman

  DOI：10.1021/acs.orglett.5b00910

  日期：2015.5.15

  The first examples of cobalt(III)-catalyzed C–H bond addition to isocyanates are described, providing a convergent strategy for arene and heteroarene amidation. Using a robust air- and moisture-stable catalyst, this transformation demonstrates a broad isocyanate scope and good functional-group compatibility and has been performed on gram scale.

  描述了钴（II​​I）催化的 C-H 键加成到异氰酸酯的第一个例子，为芳烃和杂芳烃酰胺化提供了聚合策略。使用对空气和湿气稳定的催化剂，该转化表现出广泛的异氰酸酯范围和良好的官能团相容性，并且已在克规模上进行。
• Identification of the Side Products That Diminish the Yields of the Monoamidated Product in Metal-Catalyzed C–H Amidation of 2-Phenylpyridine with Arylisocyanates
  作者：Alasdair I. McKay、Weam A. O. Altalhi、Lachlan E. McInnes、Milena L. Czyz、Allan J. Canty、Paul S. Donnelly、Richard A. J. O’Hair

  DOI：10.1021/acs.joc.9b02831

  日期：2020.2.21

  The Ru(II)-catalyzed amidation of 2-arylpyridines with aryl isocyanates via C-H bond activation is less efficient than described previously, due to the formation of a series of side products, which were readily identified using direct infusion electrospray mass spectrometry and high-performance liquid chromatography-mass spectrometry.

  由于形成了一系列副产物，这些副产物可以通过直接注入电喷雾质谱法和高效液相色谱法进行快速鉴定，因此，Ru（II）通过CH键活化将2-芳基吡啶与异氰酸芳基酯催化的酰胺化反应效率不如先前所述。高效液相色谱-质谱联用。