4,4'-diacetyl azoxybenzene | 24122-72-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4'-diacetyl azoxybenzene
• 英文别名: (Z)-1,2-bis(4-acetylphenyl)diazene 1-oxide；4,4'-diacetylazoxybenzene；bis-(4-acetyl-phenyl)-diazene-N-oxide；Bis-(4-acetyl-phenyl)-diazen-N-oxid；4.4'-Diacetyl-azoxybenzol；p.p'-Azoxyacetophenon
• CAS: 24122-72-3
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: MNNVAGPAUHKHNU-ZCXUNETKSA-N

物化性质

• 熔点：
  190-191 °C(Solv: methanol (67-56-1))
• 沸点：
  488.6±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.57
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,4'-diacetyl azoxybenzene 、 硫酸 以2%的产率得到
  参考文献：
  名称：

  SHIMAO, ICHIRO;OAE, SHIGERU, BULL. CHEM. SOC. JAP., 1983, 56, N 2, 643-644

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氨基苯乙酮 在 双氧水 、 sodium 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 10.0h， 生成 4,4'-diacetyl azoxybenzene
  参考文献：
  名称：

  邻位取代的乙氧基苯的新转变

  摘要：

  DOI：

  10.1007/bf00514470

文献信息

• Convergent Paired Electrochemical Synthesis of Azoxy and Azo Compounds: An Insight into the Reaction Mechanism
  作者：Ali Sadatnabi、Niloofar Mohamadighader、Davood Nematollahi

  DOI：10.1021/acs.orglett.1c02304

  日期：2021.8.20

  convergent paired electrochemical method was developed for the synthesis of azoxy and azo compounds starting from the corresponding nitroarenes. We propose a unique mechanism for electrosynthesis of azoxy and azo compounds. We find that both anodic and cathodic reactions are responsible for the synthesis of these compounds. The synthesis of azoxy and azo derivatives have been successfully performed in an undivided

  开发了一种收敛配对电化学方法，用于从相应的硝基芳烃开始合成偶氮和偶氮化合物。我们提出了一种独特的偶氮和偶氮化合物电合成机制。我们发现阳极和阴极反应都负责这些化合物的合成。偶氮和偶氮衍生物的合成已在未分隔的电池中成功进行，使用碳棒电极，在室温下通过恒流电解。
• REDUCTION OF AROMATIC AND ALIPHATIC NITRO COMPOUNDS BY SODIUM HYDROGEN TELLURIDE
  作者：Atsuhiro Osuka、Hirohito Shimizu、Hitomi Suzuki

  DOI：10.1246/cl.1983.1373

  日期：1983.9.5

  Various nitro compounds were effectively reduced by sodium hydrogen telluride in good yields. Thus, reductive conversion of unhindered nitrobenzenes to azoxybenzenes, sterically hindered nitrobenzenes to anilines, nitroalkanes to dimer of nitrosoalkanes, and vicinal-dinitroalkane to olefin was achieved.

  各种硝基化合物被碲化氢钠以良好的收率有效还原。因此，实现了不受阻碍的硝基苯还原转化为偶氮苯，空间位阻硝基苯还原转化为苯胺，硝基烷烃还原转化为亚硝基烷烃的二聚体，以及连位二硝基烷烃还原转化为烯烃。
• Cadmium Chloride-Zinc Catalysed Selective Reduction of Nitro Aromatics to Azoxy Compounds
  作者：Bipul Baruah、Anima Boruah、Dipak Prajapati、Jagir S. Sandhu

  DOI：10.1246/cl.1996.351

  日期：1996.5

  Treatment of aromatic nitro compounds with cadmium chloride-metallic zinc combination systems has been shown to display a good reaction selectivity in the formation of symmetrical azoxy compounds in high yields.

  用氯化镉-金属锌组合系统处理芳香硝基化合物已显示出在高产率形成对称偶氮化合物方面的良好反应选择性。
• Selective reduction of aromatic nitroso compounds with baker's yeast under neutral condition
  作者：Woonphil Baik、Jong Uk Rhee、Sang Hwi Lee、Nam Ho Lee、Byeong Hyo Kim、Kyung Soon Kim

  DOI：10.1016/0040-4039(95)00398-v

  日期：1995.4

  Aromatic nitroso compounds containing halogen and other labile substituents were selectively and rapidly reduced to their corresponding amino derivatives in good yields using Bakers' Yeast at 80 °C.

  使用贝克斯酵母，在80°C下，将含有卤素和其他不稳定取代基的芳香亚硝基化合物有选择地快速还原为相应的氨基衍生物。
• Photochemistry of<i>p</i>-Nitroacetophenone in 2-Propanol
  作者：Yuh-Nong Lin、Guang-Yan Jeng、Tung-Tan Chan、Giann-Feng Yen、Yin-Gang Wong

  DOI：10.1002/jccs.199800050

  日期：1998.4

  AbstractUpon irradiation in 2‐propanol, p‐nitroacetophenone 1 was reduced via the triplet state to p‐hydroxyaminoacetophenone 5 which was further reduced to p‐aminoacelophenone 2 and 4,4′‐diacetylazobenzene 4. Similar irradiation of 5 also gave 2 and 4, and its oxidation by oxygen gave 4,4′‐diacetylazoxybenzene 3. Photolysis of monomeric p‐nitrosoacetophenone 6 afforded acetophenone and 3 that were not produced during the irradiation of 1. Possible photoreaction pathways were discussed on the basis of published mechanisms.