4-(2-(phenylthio)ethyl)benzonitrile | 108717-94-8

• 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: 4-(2-(phenylthio)ethyl)benzonitrile
• 英文别名: 4-(2-Phenylsulfanylethyl)benzonitrile
• CAS: 108717-94-8
• 化学式: C₁₅H₁₃NS
• 分子量: 239.341
• InChiKey: XKAQRSXAHHGYLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氯苯甲腈 、 苯基乙烯基硫醚 在 naphthonitrile 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到4-(2-(phenylthio)ethyl)benzonitrile
  参考文献：
  名称：

  Aryl radicals from electrochemical reduction of aryl halides. Addition on olefins

  摘要：

  Aryl radicals generated by direct and indirect (by means of an aromatic anion radical mediator) electrochemistry are reacted with olefins in liquid ammonia and in organic solvents (Me2SO, MeCN, DMF). The arylated product is obtained in good yield in the latter case. In pure liquid NH3, the yields are extremely poor. They are improved upon addition of a proton donor such as urea or water; further increase of yields is obtained upon addition of 2-propanol. A reaction mechanism is proposed based on these observations and on the results of deuterium incorporation experiments. Cyclic voltammetry is used to determine the rate constant of the key step in the mechanism, viz, the addition of the aryl radical to the olefin, through its competition with its reaction with nucleophiles in the framework of an S(RN)1 substitution process.

  DOI：

  10.1021/jo00002a020

文献信息

• Aerial dioxygen activation <i>vs.</i> thiol–ene click reaction within a system
  作者：Khokan Choudhuri、Arkalekha Mandal、Prasenjit Mal

  DOI：10.1039/c8cc01359d

  日期：——

  Markovnikov or anti-Markovnikov selective thiol–ene click (TEC) reactions and the synthesis of β-hydroxysulfides via aerial dioxygen activation are prevalent C–S bond forming reactions of styrenes and thiophenols. Herein, by choosing appropriate environments using solvents with additives or neat conditions, any one of these three reactions was achieved exclusively in excellent yields.

  Markovnikov或反Markovnikov选择性硫醇-烯点击（TEC）反应和通过空中双氧活化合成β-羟基硫化物是苯乙烯和硫酚的常见C-S键形成反应。在本文中，通过使用具有添加剂的溶剂或在纯净条件下选择合适的环境，这三个反应中的任何一个仅以优异的收率实现。