1,2-bis(3,5-dimethoxyphenyl)diazene | 137720-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 1,2-bis(3,5-dimethoxyphenyl)diazene
• 英文别名: (E)-Bis(3,5-dimethoxyphenyl)diazene；bis(3,5-dimethoxyphenyl)diazene
• CAS: 137720-85-5
• 化学式: C₁₆H₁₈N₂O₄
• 分子量: 302.33
• InChiKey: NRCMMNVNZJXRCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  462.1±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-bis(3,5-dimethoxyphenyl)diazene 在 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 4.0h， 以89%的产率得到1,2-bis(3,5-dimethoxyphenyl)hydrazine
  参考文献：
  名称：

  Reaction of azoarenes with tributyltin hydride

  摘要：

  Tributyltin hydride when reacted with a series of substituted azoarenes afforded hydrazo compounds with high chemoselectivity and good to high yields. With ortho-substituted azoarenes, mixtures of hydrazo derivatives and N-heterocycles or cyclic products only were obtained. The kinetic law of the process was determined in the presence and in the absence of AIBN; with the radical initiator the reaction proceeds via a radical chain mechanism, whereas without AIBN the presence of stannyl free radicals could be discarded. The mechanism of the noninitiated reaction is discussed. EPR characterization of spin adducts obtained by reacting group IVB organometallic radicals with azo compounds is reported.

  DOI：

  10.1021/jo00028a038
• 作为产物：
  描述：

  3,5-二甲氧基苯胺 在 dipotassium peroxodisulfate 、 potassium carbonate 作用下， 反应 12.0h， 以80%的产率得到1,2-bis(3,5-dimethoxyphenyl)diazene
  参考文献：
  名称：

  室温下聚乙二醇中伯胺的无过渡金属氧化偶联：胺，偶氮苯，苯并噻唑和二硫化物的合成

  摘要：

  已开发出一种无过渡金属的方案，用于伯胺与亚胺和偶氮苯的氧化偶联，巯基与二硫化物的氧化偶联以及2-氨基硫酚与苯并噻唑的氧化偶联，具有优异的收率。当前环境友好方法的优势包括使用可生物相容的绿色反应条件，例如溶剂，室温反应，无过渡金属的方法。此外，它提供了更广阔的基板范围。

  DOI：

  10.1002/ejoc.201801610

文献信息

• Transition Metal-Free Oxidative Coupling of Primary Amines in Polyethylene Glycol at Room Temperature: Synthesis of Imines, Azobenzenes, Benzothiazoles, and Disulfides
  作者：Abhinandan D. Hudwekar、Praveen K. Verma、Jaspreet Kour、Shilpi Balgotra、Sanghapal D. Sawant

  DOI：10.1002/ejoc.201801610

  日期：2019.2.14

  A transition metal‐free protocol has been developed for the oxidative coupling of primary amines to imines and azobenzenes, thiols to disulfides, and 2‐aminothiophenols to benzothiazoles, offering excellent yields. The advantageous features of the present environmentally benign methodology include the usage of biocompatable and green reaction conditions such as solvent, room temperature reactions,

  已开发出一种无过渡金属的方案，用于伯胺与亚胺和偶氮苯的氧化偶联，巯基与二硫化物的氧化偶联以及2-氨基硫酚与苯并噻唑的氧化偶联，具有优异的收率。当前环境友好方法的优势包括使用可生物相容的绿色反应条件，例如溶剂，室温反应，无过渡金属的方法。此外，它提供了更广阔的基板范围。
• A General Method to Diverse Cinnolines and Cinnolinium Salts
  作者：Dongbing Zhao、Qian Wu、Xiaolei Huang、Feijie Song、Taiyong Lv、Jingsong You

  DOI：10.1002/chem.201300155

  日期：2013.5.10

  Rhodium catalysis: A highly efficient and general method has been established to prepare cinnolines, cinnolinium salts, and polycyclic cinnolinium salts through the rhodium(III)‐catalyzed oxidative CH activation/cyclization of azo compounds with alkynes (see scheme). Key features of this methodology include the unprecedented capacity to create both cinnoline and cinnolinium frameworks.

  铑催化：已经建立了一种高效且通用的方法，通过铑（III）催化的炔烃对偶氮化合物的氧化CH活化/环化反应来制备cinnoline，cinnolinium盐和多环cinnolinium盐（参见方案）。该方法的主要特点包括创建辛诺啉和cinnolinium框架的空前能力。
• Study on the Isomerization of Amphiphilic Azobenzene Cored Dendrimer and Its Molecular Environment
  作者：Michitaka Mamiya、Shun Fukushima、Tatsuo Arai

  DOI：10.1246/bcsj.20180089

  日期：2018.9.15

  3,3′,5,5′-tetramethoxy azobenzene (TMAB) and amphiphilic azobenzene dendrimers (AGn-azo) bearing triethylene glycol were synthesized and their isomerization behavior investigated. The solvation str...

  合成了带有三甘醇的3,3',5,5'-四甲氧基偶氮苯(TMAB)和两亲性偶氮苯树枝状聚合物(AGn-azo)，并研究了它们的异构化行为。溶解力...
• Rh(III)-Catalyzed Synthesis of Indazolo[2,3-<i>a</i>]quinolines: Vinylene Carbonate as C1 and C2 Building Blocks
  作者：Wei Hu、Chao Pi、Di Hu、Xiliang Han、Yangjie Wu、Xiuling Cui

  DOI：10.1021/acs.orglett.2c00580

  日期：2022.4.15

  rhodium-catalyzed cyclization of azobenzenes and vinylene carbonate via C–H bond activation to construct indazolo[2,3-a]quinolines has been developed. This protocol offers an efficient method for synthesis of the titled products in good yields with broad functional group tolerance. In this reaction, three C–C bonds and C–N bond are formed in one pot, and vinylene carbonate (VC) acts as C1 and C2 synthons as well as

  铑催化偶氮苯和碳酸亚乙烯酯通过C-H键活化环化制备吲唑并[2,3- a ]喹啉。该协议提供了一种有效的方法来合成具有广泛功能组耐受性的高产量的标题产品。在这个反应中，三个C-C键和C-N键在一锅中形成，并且碳酸亚乙烯酯（VC）作为C1和C2合成子以及“亚乙烯基转移”剂和酰化剂构建目标融合杂环。此外，这些产品表现出良好的荧光特性，表明它们具有作为荧光材料和生物传感器的潜在应用。
• Reaction of azoarenes with tributyltin hydride
  作者：Angelo Alberti、Nicola Bedogni、Massimo Benaglia、Rino Leardini、Daniele Nanni、Gian Franco Pedulli、Antonio Tundo、Giuseppe Zanardi

  DOI：10.1021/jo00028a038

  日期：1992.1

  Tributyltin hydride when reacted with a series of substituted azoarenes afforded hydrazo compounds with high chemoselectivity and good to high yields. With ortho-substituted azoarenes, mixtures of hydrazo derivatives and N-heterocycles or cyclic products only were obtained. The kinetic law of the process was determined in the presence and in the absence of AIBN; with the radical initiator the reaction proceeds via a radical chain mechanism, whereas without AIBN the presence of stannyl free radicals could be discarded. The mechanism of the noninitiated reaction is discussed. EPR characterization of spin adducts obtained by reacting group IVB organometallic radicals with azo compounds is reported.