(E)-N-benzyl-N-(1-bromo-2-(4-methoxyphenyl)vinyl)-4-methylbenzenesulfonamide | 1422721-70-7

• 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: (E)-N-benzyl-N-(1-bromo-2-(4-methoxyphenyl)vinyl)-4-methylbenzenesulfonamide
• 英文别名: N-benzyl-N-[(E)-1-bromo-2-(4-methoxyphenyl)ethenyl]-4-methylbenzenesulfonamide
• CAS: 1422721-70-7
• 化学式: C₂₃H₂₂BrNO₃S
• 分子量: 472.403
• InChiKey: KVFYFMPONRGIJY-KQWNVCNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-benzyl-N-((4-methoxyphenyl)ethynyl)-4-methylbenzenesulfonamide 在 三甲基溴硅烷 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 以99%的产率得到(E)-N-benzyl-N-(1-bromo-2-(4-methoxyphenyl)vinyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Regio- and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation

  摘要：

  A facile approach to (E)-alpha-haloenamide moieties from ynamides using bromo- or iodotrimethylsilane is described. The simple protocol enables a regio- and stereospecific hydrohalogenation of the triple bond in gram-scale and provides a general entry for synthesis of novel enamide analogues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.101

文献信息

• Brønsted acid-catalyzed α-halogenation of ynamides from halogenated solvents and pyridine-N-oxides
  作者：Seung Woo Kim、Tae-Woong Um、Seunghoon Shin

  DOI：10.1039/c6cc10286g

  日期：——

  The keteniminium ions generated from the protonation of ynamides formed reversible adducts with counter anions and pyridine-N-oxides as well as halogenated solvents. Above 80 oC, the halonium ions selectively undergo...

  由乙酰胺质子化产生的酮亚胺离子与抗衡阴离子和吡啶-N-氧化物以及卤化溶剂形成可逆加合物。高于80 oC时，ha离子选择性地经历...
• Regio- and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation
  作者：Akihiro H. Sato、Kazuhiro Ohashi、Tetsuo Iwasawa

  DOI：10.1016/j.tetlet.2012.12.101

  日期：2013.3

  A facile approach to (E)-alpha-haloenamide moieties from ynamides using bromo- or iodotrimethylsilane is described. The simple protocol enables a regio- and stereospecific hydrohalogenation of the triple bond in gram-scale and provides a general entry for synthesis of novel enamide analogues. (C) 2012 Elsevier Ltd. All rights reserved.