[5-benzoyl-6-(4-bromophenyl)-1-(4-methylphenyl)sulfonyl-2H-pyridin-3-yl]-phenylmethanone | 1207681-19-3

• 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: [5-benzoyl-6-(4-bromophenyl)-1-(4-methylphenyl)sulfonyl-2H-pyridin-3-yl]-phenylmethanone
• CAS: 1207681-19-3
• 化学式: C₃₂H₂₄BrNO₄S
• 分子量: 598.517
• InChiKey: INKQIVCXKHCURL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  79.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(4-溴苄亚基)-p-甲苯磺酰胺 、 1-苯基-2-丙炔-1-酮 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以85%的产率得到[5-benzoyl-6-(4-bromophenyl)-1-(4-methylphenyl)sulfonyl-2H-pyridin-3-yl]-phenylmethanone
  参考文献：
  名称：

  PPh3-catalyzed [2 + 2 + 2] and [4 + 2] annulations: synthesis of highly substituted 1,2-dihydropyridines (DHPs)

  摘要：

  在 PPh3 催化下，活化的末端炔烃的两个单元与芳基 N-对甲苯磺酸亚胺的一个单元发生了[2 + 2 + 2]环化反应，为高取代的二氢吡啶类化合物提供了一种合成方法。在[2 + 2 + 2]环化机理的基础上，还发现了 PPh3 催化的[4 + 2]环化。

  DOI：

  10.1039/b915825a

文献信息

• Facile synthesis of highly functionalized six-membered heterocycles via PPh3-catalyzed [4+2] annulations of activated terminal alkynes and hetero-dienes: scope, mechanism, and application
  作者：Qiongmei Zhang、Tong Fang、Xiaofeng Tong

  DOI：10.1016/j.tet.2010.07.043

  日期：2010.10

  A novel [4+2] annulation between activated terminal alkynes and aza-dienes or oxo-dienes has been developed with the use of triphenylphosphine catalyst (20 mol %), which provides a facile method for synthesis of the corresponding highly functionalized dihydropyridines or dihydropyrans in good to excellent yields. The reaction mechanism has also been established, consisting formal hetero-Diels-Alder reaction catalyzed by PPh3 and [1,3]-proton transfer, which exhibits a large isotopic effect. (C) 2010 Elsevier Ltd. All rights reserved.
• PPh3-catalyzed [2 + 2 + 2] and [4 + 2] annulations: synthesis of highly substituted 1,2-dihydropyridines (DHPs)
  作者：Huimin Liu、Qiongmei Zhang、Limin Wang、Xiaofeng Tong

  DOI：10.1039/b915825a

  日期：——

  PPh3-catalyzed [2 + 2 + 2] annulations between two units of an activated terminal alkyne and one unit of an aryl N-tosylimine have been developed to provide a synthetic method for highly substituted dihydropyridines. On the basis of the mechanism of the [2 + 2 + 2] annulation, PPh3-catalyzed [4 + 2] annulations have also been discovered.

  在 PPh3 催化下，活化的末端炔烃的两个单元与芳基 N-对甲苯磺酸亚胺的一个单元发生了[2 + 2 + 2]环化反应，为高取代的二氢吡啶类化合物提供了一种合成方法。在[2 + 2 + 2]环化机理的基础上，还发现了 PPh3 催化的[4 + 2]环化。