Cyclohexyl-(4-methoxy-phenyl)-diazene | 141320-13-0

• 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: Cyclohexyl-(4-methoxy-phenyl)-diazene
• 英文别名: Cyclohexyl-(4-methoxyphenyl)diazene
• CAS: 141320-13-0
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: UMYXUWCXHRMHEL-UHFFFAOYSA-N

物化性质

• 沸点：
  322.6±25.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  34
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Cyclohexyl-(4-methoxy-phenyl)-diazene 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 以63 %的产率得到1,2,3,4-四氢-7-甲氧基咔唑
  参考文献：
  名称：

  在氧化还原中性条件下，铜催化环烷烃与芳基重氮盐的直接碳二烯基化反应

  摘要：

  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。

  DOI：

  10.1016/j.jcat.2023.05.015
• 作为产物：
  描述：

  碘环己烷 、 甲氧苯胺 在 硫酸 、 双氧水 、 二甲基亚砜 、 sodium nitrite 作用下， 生成 Cyclohexyl-(4-methoxy-phenyl)-diazene
  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

• Rhodium(III)-Catalyzed Synthesis of Cinnolinium Salts from Azobenzenes and Diazo Compounds
  作者：Xiaohong Chen、Guangfan Zheng、Guoyong Song、Xingwei Li

  DOI：10.1002/adsc.201800326

  日期：2018.8.6

  A Rh(III)‐catalyzed C−H activation of azobenzenes in the coupling with diazo compounds has been realized, providing a straightforward strategy to access functionalized cinnolinium triflates in high yields. This protocol features silver free mild reaction conditions and compatibility with diverse functional groups. The coupling proceeds via initial Rh(III)‐catalyzed C−H alkylation, followed by zinc

  与重氮化合物偶合后，已实现了Rh（III）催化的偶氮苯的CH活化，从而提供了一种直接的方法来以高收率获得官能化的三氟甲烷磺酸。该协议的特点是无银温和的反应条件以及与各种官能团的相容性。偶联过程通过最初的Rh（III）催化的CH烷基化反应进行，随后是三氟甲磺酸锌介导的环化反应，其中三氟甲磺酸锌既充当路易斯酸又是三氟甲磺酸来源。
• Co-SAC catalyzed utilization of methanol and ethanol in the transfer hydrogenation of azo bonds: experimental and theoretical studies
  作者：Dibyajyoti Panja、Sadhan Dey、Rohini Saha、Rajib Sahu、Gourab Kanti Das、Preeti Bhobe、Sabuj Kundu

  DOI：10.1039/d3gc02725b

  日期：——

  Selective TH of amine surrogates to their corresponding primary amines using methanol or ethanol is difficult as mono/di-alkylated amines are produced as the major products. Notably, the TH of azo bonds to amines has not been reported yet. Herein, using Co-SAC, various azo compounds including commercially used dyes were effectively transfer hydrogenated to the corresponding primary amines, using ethanol

  使用甲醇和乙醇作为氢源的非极性键的转移氢化（TH）是一个巨大的挑战，而开发高效的3d金属基催化剂来完成此类反应是一个令人兴奋的探索领域。使用甲醇或乙醇将胺替代物选择性 TH 为其相应的伯胺是困难的，因为生产的主要产品是单/二烷基化胺。值得注意的是，偶氮键与胺的 TH 尚未有报道。在此，使用Co-SAC，使用乙醇和甲醇作为氢源，将包括市售染料在内的各种偶氮化合物有效地转移氢化为相应的伯胺。进行了几个对照实验来了解这一催化过程。哈米特研究表明，具有供电子取代基的底物更适合转移氢化。为了更深入地了解该机制，我们进行了 DFT 计算，揭示了醇脱氢和 -N N- 键氢化分别通过 β-氢化物消除和 Co-氢化物插入途径发生。
• Polar effects in reactions of carbon-centered radicals with diazonium salts: free-radical diazo coupling
  作者：Francesco Minisci、Fausta Coppa、Francesca Fontana、Giuseppe Pianese、Lihua Zhao

  DOI：10.1021/jo00040a038

  日期：1992.7

  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.
• 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。