(4-bromophenyl)-oxido-phenyliminoazanium | 16054-48-1

• 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: (4-bromophenyl)-oxido-phenyliminoazanium
• 英文别名: (Z)-1-phenyl-2-(4-bromophenyl)diazene 1-oxide；(Z)-2-(4-bromophenyl)-1-phenyldiazene 1-oxide；1-(4-bromophenyl)-2-phenyldiazene 2-oxide；trans-4-bromo-ONN-azoxybenzene；4-bromo-ONN-azoxybenzene；(Z)-N'-(4-bromo-phenyl)-N-phenyl-diazene-N-oxide；(Z)-N'-(4-Brom-phenyl)-N-phenyl-diazen-N-oxid
• CAS: 16054-48-1；81701-80-6；81701-81-7
• 化学式: C₁₂H₉BrN₂O
• 分子量: 277.12
• InChiKey: IJSMCPPOACMPAN-PFONDFGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.43
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4-bromophenyl)-oxido-phenyliminoazanium 以16%的产率得到
  参考文献：
  名称：

  SHIMAO ICHIRO; HASHIDZUME HIROKAZU, BULL. CHEM. SOC. JAP. , 1976, 49, NO 3, 754-757

  摘要：

  DOI：
• 作为产物：
  描述：

  azoxybenzene 在 溴 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以70%的产率得到(4-bromophenyl)-oxido-phenyliminoazanium
  参考文献：
  名称：

  trans-4-Bromo-ONN-azoxybenzene at 100 K

  摘要：

  The crystal structure of the alpha isomer of trans-4-bromoazoxybenzene [systematic name: trans-1-(bromophenyl)-2-phenyldiazene 2-oxide], C12H9BrN2O, has been determined by X-ray diffraction. The geometries of the two molecules in the asymmetric unit are slightly different and are within similar to0.02 Angstrom for bond lengths, similar to2degrees for angles and similar to3degrees for torsion angles. The azoxy bridges in both molecules have the typical geometry observed for trans-azoxybenzenes. The crystal network contains two types of planar molecules arranged in columns. The torsion angles along the Ar-N bonds are only 7 (2)degrees, on either side of the azoxy group.

  DOI：

  10.1107/s0108270104007103

文献信息

• Rh(III)-Catalyzed Regio- and Chemoselective [4 + 1]-Annulation of Azoxy Compounds with Diazoesters for the Synthesis of 2<i>H</i>-Indazoles: Roles of the Azoxy Oxygen Atom
  作者：Zhen Long、Zhigang Wang、Danni Zhou、Danyang Wan、Jingsong You

  DOI：10.1021/acs.orglett.7b00631

  日期：2017.6.2

  tandem C–H alkylation/intramolecular decarboxylative cyclization of azoxy compounds with diazoesters for the synthesis of 3-acyl-2H-indazoles is disclosed. The azoxy instead of the azo group enables a distinct approach for cyclative capture, leading to a [4 + 1]-annulation rather than a classic [4 + 2] manner. The azoxy oxygen atom is traceless after annulation, and further removal from the product is

  揭示了用Rh（III）催化的重氮化合物与重氮酸酯的串联C–H烷基化/分子内脱羧环化反应，可合成3-酰基-2 H-吲唑。取代偶氮基团的是偶氮氧基团，从而实现了一种独特的环化捕获方法，从而导致了[4 +1]环化，而不是经典的[4 + 2]方式。环氧化后，z氧基氧原子是无痕的，不需要进一步从产物中除去。该反应具有对不对称的乙氧基苯的完全区域选择性和单芳基二烯氧化物的相容性。
• Towards the Synthesis of Azoacetylenes
  作者：Frédéric Denonne、Paul Seiler、François Diederich

  DOI：10.1002/hlca.200390252

  日期：2003.9

  The synthesis of azoacetylenes (=dialkynyldiazenes) 1 and 2 has been investigated. They represent a still elusive class of chromophores with potentially very interesting applications as novel bistable photochemical molecular switches or as antitumor agents (Fig. 1). Our synthetic efforts have led us alongside three different approaches (Scheme 1). In a first route, it was envisioned to generate the

  已研究了偶氮乙炔（=二炔基二氮烯）1和2的合成。它们代表了仍难以捉摸的发色团，具有潜在的非常有趣的应用，如新型双稳态光化学分子开关或抗肿瘤剂（图1）。我们的综合努力使我们与三种不同的方法（方案1）并驾齐驱。在第一种途径中，设想通过光解N，N'-二乙炔基化的1,3,4-噻二唑烷-2,5-二酮（本身是具有挑战性的靶标）来产生偶氮（=二氮烯）键（方案2）。描述了通过将母体杂环与取代的炔基碘化铵盐进行炔基化来获得后者的尝试。在概念上类似的方法中，无少挑战性dialkynylated 9,10-二氢-9,10- diazanoanthracene（29）是由未取代的肼的炔基化而产生28（方案6）。在第二种途径中，尝试以涉及氮杂双（磷烷）36和（三异丙基甲硅烷基）烯酮37之间的氮杂-维蒂希反应的合成方案，尝试从Br-取代的二亚乙烯基肼（酮-嗪）35生成NN键（方案7）。）。最后，探索了第三种方法，该方
• Rh(III)-Catalyzed [4 + 1]-Annulation of Azoxy Compounds with Alkynes: A Regioselective Approach to 2<i>H</i>-Indazoles
  作者：Zhen Long、Yudong Yang、Jingsong You

  DOI：10.1021/acs.orglett.7b00982

  日期：2017.6.2

  A rhodium-catalyzed regioselective C–H activation/cyclization of azoxy compounds with alkynes has been disclosed to construct a variety of 2H-indazoles. A [4 + 1]-cycloaddition rather than a normal [4 + 2] mode is observed in the process of cyclative capture along with an oxygen-atom transfer and a C≡C triple bond cleavage. This protocol features a broad substrate scope, a good functional group tolerance

  铑催化炔烃对偶氮化合物的区域选择性C–H活化/环化反应已被证实可构建多种2 H-吲唑。在循环捕获的过程中观察到[4 +1]-环加成而不是正常的[4 +1]模式，以及氧原子转移和C≡C三键裂解。该协议具有广泛的底物范围，良好的官能团耐受性和独特的区域选择性。
• Synthesis of Unsymmetrical Azoxyarenes via Copper‐Catalyzed Aerobic Oxidative Dehydrogenative Coupling of Anilines with Nitrosoarenes
  作者：Chongyang Shi、Boxia Xu、Xiaolan Fang、Xiaochun Yu、Huile Jin、Shun Wang

  DOI：10.1002/adsc.202001526

  日期：2021.3.29

  A copper‐catalyzed oxidative dehydrogenative coupling of nitrosobenzenes with anilines for the synthesis of unsymmetrical azoxybenzenes was developed. This approach uses O2 as the oxidant. The reaction products are diverse unsymmetrical azoxybenzenes rather than azobenzenes, which are obtained in the Mills reaction. The use of an inexpensive copper catalyst, a broad substrate scope, and mild reaction

  开发了铜催化的亚硝基苯与苯胺的氧化脱氢偶联反应，用于合成不对称的乙氧基苯。该方法使用O 2作为氧化剂。反应产物是多种不对称的乙氧基苯而不是在米尔斯反应中获得的偶氮苯。廉价铜催化剂的使用，广泛的底物范围和温和的反应条件使该方案成为制备不对称氮氧基化合物的原子经济和分步骤经济的方法。
• Arylazostilbene und -tolane durch Heck-Reaktion
  作者：Cheung-Bok Jeoung、Oliver Haak、Walter Grahn、Peter Boldt

  DOI：10.1002/prac.19933350605

  日期：——

  The palladium-catalysed coupling of p-bromo azo dyes 4 with styrenes 6 and arylacetylenes 9 provides arylazostilbenes 7 and -tolanes 10, respectively, in fair-to-good yields. Likewise, coupling of azoxy compound 5 with styrenes 6 forms the arylazoxystilbenes 8 in high yields. The influence of substituentes on light absorption of the new dyes as well as on the the C-13-NMR shifts of the azotolanes 10 are discussed.