(4-Chlorophenyl)-cyclohexyldiazene | 80228-00-8

• 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-Chlorophenyl)-cyclohexyldiazene
• CAS: 80228-00-8
• 化学式: C₁₂H₁₅ClN₂
• 分子量: 222.718
• InChiKey: UYCCMLXEZJGHST-UHFFFAOYSA-N

物化性质

• 沸点：
  310.2±25.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  碘环己烷 、 对氯苯胺 在 硫酸 、 双氧水 、 二甲基亚砜 、 sodium nitrite 作用下， 生成 (4-Chlorophenyl)-cyclohexyldiazene
  参考文献：
  名称：

  Polar effects in reactions of carbon-centered radicals with diazonium salts: free-radical diazo coupling

  摘要：

  Carbon-centered radicals react with diazonium salts by addition, leading under reductive conditions to azo derivatives (free-radical diazocoupling), or by electron-transfer in chain processes. The reaction is highly sensitive to polar effects and it has been investigated by three different processes: (i) alkyl radicals, generated from alkyl iodides, H2O2, Fe(II) salt, and DMSO, have been utilized to develop a new general synthesis of alkylarylazo compounds; (ii) the reaction of aryl radicals with diazonium salts in the presence of Ti(III) or Fe(II) salts has been investigated, also in relation to the fact that the reaction products (azoarenes and biaryls) are often detected as side products in classical organic reactions of diazonium salts, catalyzed by Cu(I) salts, such as the Sandmeyer, Meerwein, and Pschorr reactions; (iii) adducts from addition of aryl radicals to vinyl acetate or vinyl ether react with diazonium salts either by diazocoupling reaction or by electron-transfer; a general synthesis of [alpha-(acyl-oxy)alkyl]arylazo compounds has been developed.

  DOI：

  10.1021/jo00040a038

文献信息

• Copper-catalyzed direct carbodiazenylation of cycloalkanes with aryldiazonium salts under redox neutral conditions
  作者：Fengxiang Zhu、Jiajia Luo、Xiao-Feng Wu

  DOI：10.1016/j.jcat.2023.05.015

  日期：2023.8

  Diazenes are of particular importance in organic synthesis and routinely utilized as dyes, photoswitches, indicators, radical reaction initiators, food additives, and pharmaceuticals. In this work, a novel copper-catalyzed direct carbodiazenylation of cycloalkanes with aryldiazonium salts toward the synthesize of alkylarylazo compounds has been developed. The reaction can be carried out under redox

  二氮烯在有机合成中特别重要，通常用作染料、光开关、指示剂、自由基反应引发剂、食品添加剂和药物。在这项工作中，开发了一种新型铜催化的环烷烃与芳基重氮盐的直接碳二烯基化反应，用于合成烷基芳基偶氮化合物。该反应可以在氧化还原中性条件下进行，该条件允许使用高度功能化的底物，并且可以以中等到良好的收率生产各种二氮烯。值得注意的是，该过程在温和条件下运行，然后可以直接制备吲哚。
• Free-radical diazocoupling. A new general reaction of diazonium salts
  作者：Attilio Citterio、Francesco Minisci

  DOI：10.1021/jo00348a033

  日期：1982.4