dimethyl 4,4'-azoxydibenzoate | 23663-92-5

• 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: dimethyl 4,4'-azoxydibenzoate
• 英文别名: 4,4'-azoxybenzoic acid dimethyl ester；Azoxybenzol-4,4'-dicarbonsaeure-dimethylester；Benzoic acid, 4,4'-azoxybis-, dimethyl ester；(4-methoxycarbonylphenyl)-(4-methoxycarbonylphenyl)imino-oxidoazanium
• CAS: 23663-92-5
• 化学式: C₁₆H₁₄N₂O₅
• 分子量: 314.298
• InChiKey: INGGHTRXJNSSLR-UHFFFAOYSA-N

物化性质

• 熔点：
  204-205 °C
• 沸点：
  480.5±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲基4-(羟基氨基)苯甲酸酯 在 sodium hydroxide 、 氧气 作用下， 反应 4.0h， 以88%的产率得到dimethyl 4,4'-azoxydibenzoate
  参考文献：
  名称：

  Synthesis Of N-Arylhydroxylamines by Antimony-Catalyzed Reduction of Nitroarenes

  摘要：

  Metallic antimony catalyzes the reduction of aromatic nitro compounds to the corresponding N-arylhydroxylamines in good yields with NaBH4 under mild conditions. The azoxybenzenes from autoxidation of N-arylhydroxylamines were also obtained in basic conditions.

  DOI：

  10.1080/00397919708006092

文献信息

• Highly selective conversion of nitrobenzenes using a simple reducing system combined with a trivalent indium salt and a hydrosilane
  作者：Norio Sakai、Kohji Fujii、Shinya Nabeshima、Reiko Ikeda、Takeo Konakahara

  DOI：10.1039/c000383b

  日期：——

  Controlling the type of indium salt and hydrosilane enables a highly selective reduction of aromatic nitro compounds into three coupling compounds, azoxybenzenes, azobenzenes and diphenylhydrazines, and one reductive compound, anilines.

  控制铟盐与氢硅烷类型，使得对芳香硝基化合物的高度选择性还原，转化为三种偶合产物：氧化偶氮苯、偶氮苯和二苯基肼，以及一种还原性产物：苯胺。
• Continuous Flow Synthesis of Azoxybenzenes by Reductive Dimerization of Nitrosobenzenes with Gel‐Bound Catalysts
  作者：Carsten J. Schmiegel、Patrik Berg、Franziska Obst、Roland Schoch、Dietmar Appelhans、Dirk Kuckling

  DOI：10.1002/ejoc.202100006

  日期：2021.3.19

  In search for a new synthetic pathway for azoxybenzenes with different substitution patterns, an approach using a microfluidic reactor with gel‐bound proline organocatalysts under continuous flow inside a microfluidic device is presented.

  为了寻找具有不同取代方式的乙氧基苯的新合成途径，提出了一种在微流体装置内连续流动下使用带有凝胶结合的脯氨酸有机催化剂的微流体反应器的方法。
• Oxidative benzoin reactions
  作者：J. Castells、F. Pujol、H. Llitjós、M. Moreno-Mañas

  DOI：10.1016/0040-4020(82)80170-1

  日期：1982.1

  A one-pot synthesis (yields over 50%) of methyl and ethyl esters from aldehydes (and the corresponding alcohol), using aromatic nitrocompounds as oxidizing agents under the catalytic action of cyanide ion or of a conjugate base of a thiazolium ion, is described. A variety of by-products (α-hydroxybenzylidenaniline) (16), α-methoxybenzylidenaniline (21), α-cyanobenzylidenaniline (27), N1-hydroxy-N1

  描述了在氰化物离子或噻唑鎓离子的共轭碱的催化作用下，使用芳香族硝基化合物作为氧化剂，由醛（和相应的醇）一锅法合成（收率超过50％）甲基和乙基酯的方法。 。已经产生了多种副产物（α-羟基苄基苯胺（16），α-甲氧基苄基苯胺（21），α-氰基苄基苯胺（27），N 1-羟基-N 1，N 2-二苯基苯甲m （28）等）。确定。
• Mild, selective and switchable transfer reduction of nitroarenes catalyzed by supported gold nanoparticles
  作者：Xiang Liu、Sen Ye、Hai-Qian Li、Yong-Mei Liu、Yong Cao、Kang-Nian Fan

  DOI：10.1039/c3cy00533j

  日期：——

  A highly versatile and flexible gold-based catalytic system has been developed for the controlled and selective transfer reduction of nitroarene using 2-propanol as a convenient hydrogen source under mild conditions. Depending on the specific reaction conditions, multiple products including azoxyarenes, symmetric or asymmetric azoarenes and anilines can be obtained respectively via a controlled reduction of the nitro aromatics with good to excellent yields in the presence of a reusable mesostructured ceria-supported gold (Au/meso-CeO2) catalyst. The overall operational simplicity, high chemoselectivity, functional-group tolerance and reusability of the catalyst make this approach an attractive and reliable tool for organic and process chemists.

  一种基于金的通用且灵活的催化体系已被开发用于在温和条件下，使用2-丙醇作为便捷的氢源，对硝基芳烃进行可控和选择性的转移还原。根据特定的反应条件，可通过在可重复使用的介孔氧化铈负载金（Au/meso-CeO2）催化剂存在下，对硝基芳烃进行可控还原，分别获得多种产物，包括氧化偶氮苯、对称或非对称偶氮苯以及苯胺，产率从良好到优异。该方法操作简便、化学选择性高、官能团容忍度好以及催化剂的可重复使用性，使其成为有机和过程化学家的一个有吸引力和可靠的工具。
• Au@zirconium-phosphonate nanoparticles as an effective catalytic system for the chemoselective and switchable reduction of nitroarenes
  作者：Francesco Ferlin、Matteo Cappelletti、Riccardo Vivani、Monica Pica、Oriana Piermatti、Luigi Vaccaro

  DOI：10.1039/c8gc03513j

  日期：——

  Zirconium phosphate bearing aminoethyl groups on the layer surface, ZP(AEP), was used to immobilize AuNPs. The gold-based catalyst proved its high efficiency for the chemoselective reduction of nitroarenes under both batch and flow conditions by using NaBH₄ as a reducing agent.

  带有层表面氨基乙基基团的磷酸锆，ZP(AEP)，被用于固定金纳米颗粒（AuNPs）。以NaBH4作为还原剂的条件下，金基催化剂在批量和流动条件下对硝基芳烃的化学选择性还原证明了其高效性。