methyl (2-pyridin-2-ylphenyl)carbamate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl (2-pyridin-2-ylphenyl)carbamate
• 英文别名: 2-(2-pyridyl)methoxycarbamoylbenzene；methyl N-(2-pyridin-2-ylphenyl)carbamate
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: UNKFLMGIRHGPBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯基吡啶 、 (Methoxycarbonylamino) acetate 在 silver hexafluoroantimonate 、 carbonyl(pentamethylcyclopentadienyl)cobalt diiodide 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以52%的产率得到methyl (2-pyridin-2-ylphenyl)carbamate
  参考文献：
  名称：

  Cobalt(III)-Catalyzed C–H Amidation of Arenes using Acetoxycarbamates as Convenient Amino Sources under Mild Conditions

  摘要：

  The Co(III)-catalyzed direct C-H amidation of arenes has been developed using O-acylcarbamates as a convenient amino source. This reaction proceeded in high efficiency under external oxidant-free conditions with a broad range of arene substrates, including 6-arylpurines bearing sensitive functional groups, thus furnishing synthetically versatile arene N-carbamate products.

  DOI：

  10.1021/cs501860b

文献信息

• Intermolecular Amidation of Unactivated sp² and sp³ C−H Bonds via Palladium-Catalyzed Cascade C−H Activation/Nitrene Insertion
  作者：Hung-Yat Thu、Wing-Yiu Yu、Chi-Ming Che

  DOI：10.1021/ja062856v

  日期：2006.7.19

  reactions. For the reaction of unactivated sp3 C-H bonds, beta-amidation of 1 degrees sp3 C-H bonds versus 2 degrees C-H bonds is preferred. The catalytic reaction is initiated by chelation-assisted cyclopalladation involving C-H bond activation. Preliminary mechanistic study suggested that the persulfate oxidation of primary amides should generate reactive nitrene species, which then reacted with the cyclopalladated

  该通讯描述了 Pd(OAc)2 催化的未活化 sp2 和 sp3 CH 键使用伯酰胺和过硫酸钾的分子间酰胺化反应。含有悬垂肟或吡啶基团的底物以优异的化学和区域选择性进行酰胺化。值得注意的是，反应性 CX 键具有良好的耐受性，并且各种伯酰胺可以成为 Pd 催化的 CH 酰胺化反应的有效亲核试剂。对于未活化的 sp3 CH 键的反应，优选 1 度 sp3 CH 键与 2 度 CH 键的 β-酰胺化。催化反应由涉及 CH 键活化的螯合辅助环钯化引发。初步机理研究表明，伯酰胺的过硫酸盐氧化应生成活性氮烯物种，
• Radical dearomatization of arenes and heteroarenes
  作者：David Crich、Mitesh Patel

  DOI：10.1016/j.tet.2006.05.051

  日期：2006.8

  The stannane-mediated benzeneselenol-catalyzed addition of aryl iodides to a range of arenes and aromatic hetereocycles has been studied. With furan, thiophene, and several carbocyclic arenes, the addition takes place with quenching of the adduct radical by the catalytic selenol leading to moderate yields of aryl-dihydroarenes. With nitrogen heterocycles, on the other hand, it was not possible to suppress aromatization of the adduct radical and fully aromatized products were isolated. Aryl iodides bearing hydrogen bond donating groups in the ortho-position add to nitrogen heterocycles with high selectivity ortho- to the nitrogen, affording a simple one-step synthesis of potential chelating ligands. While 2-iodophenol is an excellent aryl radical source in these reactions, the homologous 1-iodo-2-naphthol fails owing to its reaction with diphenyl diselenide, which gives 1-phenylseleno-2-naphthol in high yield. (c) 2006 Elsevier Ltd. All rights reserved.
• Direct Synthesis of Heterobiaryls by Radical Addition to Pyridine: Expeditious Synthesis of Chelating Ligands
  作者：David Crich、Mitesh Patel

  DOI：10.3987/com-04-s(p)34

  日期：——

  The addition of aryl radicals to pyridine may be affected in moderate yield on exposure of aryl iodides to tributyltin hydride, AIBN, and diphenyl diselenide in hot pyridine. Mixtures of ortho-, meta-, and para-aryl substituted pyridines are typically obtained. When the iodide is ortho-substituted with a hydrogen bond donor, such as o-iodophenol, significantly improved selectivity for ortho-substituted pyridines, with potential as bidentate chelating ligands, is obtained.