4-(1-hydroxy-2-(phenylthio)ethyl)benzonitrile | 119135-77-2

• 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-(1-hydroxy-2-(phenylthio)ethyl)benzonitrile
• 英文别名: 4-(1-hydroxy-2-phenylsulfanylethyl)benzonitrile
• CAS: 119135-77-2
• 化学式: C₁₅H₁₃NOS
• 分子量: 255.34
• InChiKey: PXJGVUOLFIMJKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.02
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-(2-Phenylsulfanyl-1-trimethylsilanyloxy-ethyl)-benzonitrile 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 4-(1-hydroxy-2-(phenylthio)ethyl)benzonitrile
  参考文献：
  名称：

  Hosomi, Akira; Ogata, Koichiro; Hoashi, Koichiro, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 9, p. 3736 - 3738

  摘要：

  DOI：

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。
• Solvent-mediated switching between oxidative addition and addition–oxidation: access to β-hydroxysulfides and β-arylsulfones by the addition of thiols to olefins in the presence of Oxone
  作者：Soumen Payra、Navin Yadav、Jarugu Narasimha Moorthy

  DOI：10.1039/d1nj04892a

  日期：——

  The reaction between aryl olefins and thiols in the presence of Oxone in toluene–water (9 : 1, v/v) affords β-hydroxy-2-arylethyl aryl sulfides smoothly by the interception of intermediary thiyl radicals with aryl olefins; the former are generated by the oxidation of thiols with Oxone in a biphasic medium. However, the change of the solvent system to acetonitrile–water facilitates a nonradical and

  芳基烯烃和硫醇在 Oxone 存在下在甲苯-水 (9 : 1, v/v) 中的反应通过拦截中间硫基自由基与芳基烯烃顺利地提供 β-羟基-2-芳基乙基芳基硫化物；前者是通过在双相介质中用 Oxone 氧化硫醇产生的。然而，将溶剂系统改为乙腈 - 水促进了非自由基和协同途径，仅通过串联点击反应，然后氧化。本质上，在甲苯-水介质中促进了“氧化加成”，而在乙腈-水介质中促进了“加成-氧化”。鉴于 Oxone 易于获得、环境友好且价格低廉，溶剂介导的转换构成了对两种不同产品的轻松直接访问，即 β-羟基-2-芳基乙基芳基硫化物和 2-芳基乙基芳基砜。
• Air Oxidative Radical Hydroxysulfurization of Styrenes Leading to β-Hydroxysulfides
  作者：Shao-Fang Zhou、Xiangqiang Pan、Zhi-Hao Zhou、Adedamola Shoberu、Jian-Ping Zou

  DOI：10.1021/acs.joc.5b00123

  日期：2015.4.3

  Air oxidative radical hydroxysulfurization of styrenes initiated by 0.5 mol % of tert-butyl hydroperoxide with arylthiols is described, and a new type of difunctionalization of alkenes was achieved.
• HOSOMI, AKIRA;OGATA, KOICHIRO;HOASHI, KOICHIRO;KOHRA, SHINYA;TOMINAGA, YO+, CHEM. AND PHARM. BULL., 36,(1988) N 9, C. 3736-3738
  作者：HOSOMI, AKIRA、OGATA, KOICHIRO、HOASHI, KOICHIRO、KOHRA, SHINYA、TOMINAGA, YO+

  DOI：——

  日期：——