di-1-naphthalenyl-diazene, 1-oxide | 104124-90-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: di-1-naphthalenyl-diazene, 1-oxide
• 英文别名: di-[1]naphthyl-diazene-N-oxide；Di-[1]naphthyl-diazen-N-oxid；[1.1']Azoxynaphthalin；α.α'-Azoxynaphthalin；Diazene, dinaphthalenyl-, 1-oxide；naphthalen-1-yl-naphthalen-1-ylimino-oxidoazanium
• CAS: 104124-90-5
• 化学式: C₂₀H₁₄N₂O
• 分子量: 298.344
• InChiKey: MMKPTFVTUANMAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  di-1-naphthalenyl-diazene, 1-oxide 在 sodium hydroxide 、 锌 作用下， 生成 [2,2']binaphthyl-1,1'-diyldiamine
  参考文献：
  名称：

  41.一些二萘基。第二部分。1：1'-偶氮-萘和1：1'-偶氮-萘的还原。1：1'-肼基萘的分离

  摘要：

  DOI：

  10.1039/jr9330000133
• 作为产物：
  描述：

  1-萘胺 在 双氧水 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 生成 di-1-naphthalenyl-diazene, 1-oxide
  参考文献：
  名称：

  二氧化硅包封的磁性纳米颗粒负载的Zn（II）纳米催化剂：通用的综合性，具有出色的反应性和选择性，可合成乙氧基芳烃，并具有简便的催化剂回收和可回收性

  摘要：

  通过将2-乙酰基吡啶共价接枝到胺官能化的[受电子邮件保护的]纳米颗粒上，然后用乙酸锌金属化，已经合成了新型的高效锌基纳米催化剂。发现所得的纳米复合材料对于各种芳族胺的氧化以产生氮氧杂芳烃是高度有效的。制备的纳米催化剂通过电子显微镜技术（具有EDS的SEM和TEM），X射线衍射（XRD），振动采样磁力计（VSM），傅里叶变换红外光谱（FT-IR）和原子吸收光谱（AAS）技术进行表征。与其他非磁性非均相催化体系相比，高转化率（TON），温和的反应条件和对具有持续催化活性的偶氮芳烃的高选择性使得本方案值得并高度顺应。

  DOI：

  10.1016/j.apcata.2012.12.046

文献信息

• Organocatalytic oxidation of substituted anilines to azoxybenzenes and nitro compounds: mechanistic studies excluding the involvement of a dioxirane intermediate
  作者：Errika Voutyritsa、Alexis Theodorou、Maroula G. Kokotou、Christoforos G. Kokotos

  DOI：10.1039/c6gc03174a

  日期：——

  An organocatalytic and environmentally friendly approach for the selective oxidation of substituted anilines was developed. Utilizing a 2,2,2-trifluoroacetophenone-mediated oxidation process, substituted anilines can be transformed to azoxybenzenes, while simple treatment...

  开发了有机催化和环境友好的方法来选择性氧化取代的苯胺。利用2,2,2-三氟苯乙酮介导的氧化过程，可以将取代的苯胺转化为a氧基苯，同时进行简单的处理...
• Ultrasound-accelerated selective oxidation of primary aromatic amines to azoxy derivatives with trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane catalyzed by Preyssler acid-mediated nano-TiO2
  作者：Davood Azarifar、Seyed-Mola Khatami、Zohreh Najminejad

  DOI：10.1007/s13738-013-0328-z

  日期：2014.4

  Preyssler-type heteropolyacid supported on TiO2 nanoparticles has been explored as an efficient catalyst in selective oxidation of primary aromatic amines to azoxy derivatives using trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane as oxidant. The reactions proceeded smoothly under mild and green ultrasound-accelerated conditions to afford the products in high yields. The catalyst recovered from the reaction mixture exhibits long-term stability with no significant drop in its catalytic activity. .

  以TiO2纳米粒子为载体的Preyssler型杂多酸已被探索作为高效催化剂，用于在温和且环保的超声加速条件下，使用反式3,5-二氢过氧-3,5-二甲基-1,2-二恶烷作为氧化剂，将伯芳香胺选择性氧化为偶氮氧衍生物。反应在温和条件下顺利进行，产率极高。从反应混合物中回收的催化剂显示出长期的稳定性，其催化活性没有显著下降。
• An Easy Access to Aromatic Azo Compounds under Ultrasound/Microwave Irradiation
  作者：Giancarlo Cravotto、Luisa Boffa、Marco Bia、Werner Bonrath、Massimo Curini、Georgios Heropoulos

  DOI：10.1055/s-2006-951481

  日期：2006.9

  Chemoselective reduction of nitroarenes to azo and azoxy compounds was easily achieved using zinc powder and ­ammonium chloride in DMF or DMF-water (95:5) under high intensity ultrasound (US) or microwave (MW) irradiation, separately or combined. When carried out under conventional heating the reaction required much higher temperatures and gave lower yields. The addition of a small amount of water caused a dramatic increase in the reactivity, permitting the reduction of hindered nitroarenes at the expense of selectivity. A novel reactor for combined US/MW ­irradiation was employed which demonstrated additional beneficial effects.

  利用锌粉和氯化铵在DMF或DMF-水（95:5）中，在高强度超声（US）或微波（MW）辐照下，分别或结合地很容易实现对硝基芳烃的化学选择性还原成偶氮和偶氮氧化物。当在常规加热下进行反应时，需要更高的温度且产率较低。添加少量水显著提高了反应性，使得在牺牲选择性的情况下可以还原受阻的硝基芳烃。采用了一种新型反应器用于联合US/MW辐照，显示出额外的有益效果。
• Catalytic selective oxidation of amines with hydroperoxides over molecular sieves: Investigations into the reaction of alkylamines, arylamines, allylamines and benzylamines with H2O2 and TBHP over TS-1 and CrS-2 as the new catalyst
  作者：S. Suresh、Reni Joseph、B. Jayachandran、A.V. Pol、M.P. Vinod、A. Sudalai、H.R. Sonawane、T. Ravindranathan

  DOI：10.1016/0040-4020(95)00692-2

  日期：1995.10

  The liquid phase oxidation of various substituted amines with dil H2O2 and tert-butyl hydroperoxide (TBHP) has been investigated over titanium and chromium silicates respectively. While TS-1/H2O2 combination exhibits a remarkable activity and selectivity in the oxidation of arylamines to produce the symmetrical azoxybenzenes, CrS-2 catalyzes the selective oxidation of various substituted amines to the corresponding nitro compounds by oxidation with 70% TBHP. The nature of the reactive intermediates during the oxidation of anilines to nitrobenzenes has been established using cyclic voltammetry experiments. Further, amines possessing a C-H bonds are selectively oxidized to either oximes or the carbonyl compounds on reaction with H2O2 catalyzed by TS-1.
• Cumming; Ferrier, Journal of the Chemical Society, 1925, vol. 127, p. 2375
  作者：Cumming、Ferrier

  DOI：——

  日期：——