4′-hydroxyl-4-nitroazobenzene | 81944-71-0

• 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: 4′-hydroxyl-4-nitroazobenzene
• 英文别名: 4-(4-nitrophenylazo)phenol；(E)-(4-hydroxyphenyl)(4-nitrophenyl)diazene；(E)-(2-(4-nitrophenyl)diazenyl)phenol；4-[(E)-(4-nitrophenyl)diazenyl]phenol；(E)-4-(4-nitrophenyl diazenyl)phenol；4-[(4-nitrophenyl)(azo)]phenol；4-nitro-4'-hydroxylazobenzene
• CAS: 81944-71-0
• 化学式: C₁₂H₉N₃O₃
• 分子量: 243.222
• InChiKey: NRJPVIOTANUINF-BUHFOSPRSA-N

物化性质

• 熔点：
  213 °C
• 沸点：
  467.3±30.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.09
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4′-hydroxyl-4-nitroazobenzene 在 sodium sulfide 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 4-[4-[3,4,5-tris(n-dodecan-1-yloxy)benzyloxy]phenylazo]aniline
  参考文献：
  名称：

  Phototriggered Self-Assembly of Hydrogen-Bonded Rosette

  摘要：

  Azobenzene-appended melamine M2 and barbiturate B2, both possessing bulky tridodecyloxyphenyl (TDP) wedge(s), were designed and synthesized to establish a photoresponsive hydrogen-bonded supramolecular assembly. The geometrical isomer EE-M2 bearing two E-azobenzene moieties easily complexed with 1132, affording a remarkably stable cyclic hexamer EE-M2(3)(.)B2(3) (rosette) in chloroform, toluene, and methyleyelohexane, as confirmed by size exclusion chromatography, dynamic light scattering, H-1 NMR, and UV-vis studies. The E-->Z photoisomerization of the azobenzene moieties upon irradiation with UV light was significantly suppressed in the rosette because of the steric crowding of the TDP wedges (total of nine TDP wedges in a rosette), whereas irradiation of the monomeric EE-M2 resulted in facile transformation into ZZ-M2 bearing two Z-azobenzene moieties. H-1 NMR studies of the complexation of the initially photogenerated ZZ-M2 with B2 revealed that it is hard for ZZ-M2 to form a rosette with B2 because of the intermolecular steric interaction between the TDP wedges. The photoregulatable complexation efficiency of M2 allowed us to accomplish the phototriggered formation of the rosette by irradiation of a monomeric mixture of ZZ-M2 and B2 using visible light.

  DOI：

  10.1021/ja047783z
• 作为产物：
  描述：

  (Z)-4-((4-nitrophenyl)diazenyl)phenol 以 乙醇 为溶剂， 生成 4′-hydroxyl-4-nitroazobenzene
  参考文献：
  名称：

  Photo-driven optical oscillators in the kHz range based on push–pull hydroxyazopyridines

  摘要：

  推拉偶氮苯酚是稳定光驱动光振荡器的重要目标分子。羟基氮吡啶甲基碘盐的振荡频率高达 10 kHz，连续工作时不会出现疲劳迹象。

  DOI：

  10.1039/c1cc10302d

文献信息

• Soluble Polymer-Supported Catalysts Containing Azo Dyes
  作者：David E. Bergbreiter、Philip L. Osburn、Chunmei Li

  DOI：10.1021/ol017198s

  日期：2002.3.1

  [structure: see text] Azo benzene derivatives were incorporated into soluble polymer-bound catalysts by two different approaches. The first was to attach the dye to the polymer-bound catalysts, using the dye as an innocent spectator to study the phase preference, concentration, and recoverability of a catalyst. The second approach used an azo dye as a ligand to form an effective soluble polymer-bound Pd(II)

  [结构：见正文]通过两种不同的方法将偶氮苯衍生物掺入可溶性聚合物结合的催化剂中。首先是将染料连接到与聚合物结合的催化剂上，使用该染料作为无辜的观察者来研究催化剂的相偏好，浓度和可回收性。第二种方法使用偶氮染料作为配体，以形成用于Heck反应的有效的可溶性聚合物结合Pd（II）催化剂。
• Monolayer and Bilayer Stability of Ammonium Amphiphiles Carrying an Azobenzene Unit – Effects of Substituents at the Azobenzene Unit
  作者：Marcel D. Everaars、Antonius T. M. Marcelis、Ernst J. R. Sudhölter

  DOI：10.1002/jlac.199719970106

  日期：1997.1

  double-chained ammonium amphiphiles carrying one azobenzene moiety (I) have been synthesized. The bilayer-stabilizing effect of different azobenzenes (ABs) has been investigated by measuring the “gel-to-liquid crystalline” phase transition temperatures of the formed bilayers in water using differential scanning calorimetry. It is found that the stabilizing effect of the azobenzenes strongly depends

  已经合成了带有一个偶氮苯部分（I）的新型双链铵两亲物。通过使用差示扫描量热法测量水中形成的双层的“凝胶到液晶”相变温度，已经研究了不同偶氮苯（ABs）的双层稳定作用。发现偶氮苯的稳定作用强烈地取决于芳环上的取代基。稳定效果按以下顺序增加：F
• Novel Phenyldiazenyl Fibrate Analogues as PPAR α/γ/δ Pan-Agonists for the Amelioration of Metabolic Syndrome
  作者：Letizia Giampietro、Antonio Laghezza、Carmen Cerchia、Rosalba Florio、Lucia Recinella、Fabio Capone、Alessandra Ammazzalorso、Isabella Bruno、Barbara De Filippis、Marialuigia Fantacuzzi、Claudio Ferrante、Cristina Maccallini、Paolo Tortorella、Fabio Verginelli、Luigi Brunetti、Alessandro Cama、Rosa Amoroso、Fulvio Loiodice、Antonio Lavecchia

  DOI：10.1021/acsmedchemlett.8b00574

  日期：2019.4.11

  The development of PPARα/γ dual or PPARα/γ/δ pan-agonists could represent an efficacious approach for a simultaneous pharmacological intervention on carbohydrate and lipid metabolism. Two series of new phenyldiazenyl fibrate derivatives of GL479, a previously reported PPARα/γ dual agonist, were synthesized and tested. Compound 12a was identified as a PPAR pan-agonist with moderate and balanced activity

  PPARα/γ双重或PPARα/γ/δ泛激动剂的发展可能代表一种同时进行药理干预碳水化合物和脂质代谢的有效方法。合成并测试了两个系列的新的GL479苯基二氮烯基贝特酸酯衍生物（先前报道的PPARα/γ双激动剂）。化合物12a被鉴定为对三种PPAR亚型（α，γ，δ）具有中等且平衡活性的PPAR泛激动剂。此外，对接实验表明，与PPARα或PPARδ相比，12a在PPARγ中采用不同的结合方式，为进一步的PPAR泛激动剂结构指导设计提供了结构基础。在体外均评估了12a的有益作用，关于PPAR靶向关键代谢基因的表达，以及离体在两种大鼠组织炎症模型中的作用。所获得的结果使得可以认为该化合物是开发新型PPAR泛激动剂的有趣线索，所述PPAR泛激动剂具有可用于代谢综合症治疗的活化特性。
• A New Benzannulation Reaction of Azoaromatics
  作者：Peter Quayle、Omer Rasheed、James Raftery

  DOI：10.1055/s-0034-1380450

  日期：——

  The BHQ benzannulation reaction of azo-substituted (2-allyl­aryl)trichloracetates, leading to azo-naphthalenes, is described. The scope and limitations of this new synthesis of azoaromatics is discussed.

  描述了偶氮取代的（2-烯丙基芳基）三氯乙酸酯的 BHQ 苯并环化反应，导致偶氮萘。讨论了这种新的偶氮芳烃合成的范围和局限性。
• Synthesis and characterization of photoactive columnar liquid crystals containing azobenzene and quinoxaline moieties
  作者：Welisson P. Silva、Edivandro Girotto、Hugo Gallardo、Rodrigo Cristiano

  DOI：10.1016/j.molliq.2020.112944

  日期：2020.6

  we report the synthesis and characterization of thermal and optical properties of photoactive molecules containing both quinoxaline and azobenzene moieties. Two series of molecules in which the quinoxaline is connected to the azobenzene without a flexible alkyl chain were accessed via esterification reactions between the 4-(hydroxy)-4′-substituted-azobenzenes (substituents on azobenzene ring: -ODecyl

  在这项研究中，我们报告了同时包含喹喔啉和偶氮苯部分的光敏分子的热学性质和光学性质的合成和表征。通过4-（羟基）-4'-取代的偶氮苯（偶氮苯环上的取代基：-ODecyl，-NO 2， -Cl，-OMe和-O（2-Et-己基））和2,3-双（4-甲氧基苯基）喹喔啉-6-羧酸或2,3-双（3,4-双（十二烷氧基）苯基）喹喔啉-6-羧酸。通过O获得了在两个芳族系统之间含有六个碳原子的烷基间隔基的另外两个分子上述相同的喹喔啉酸与4-（6-溴己氧基）-4'-取代的偶氮苯的-烷基化反应。喹喔啉侧缺少长烷基链会导致产生玻璃状物质，其中一些表现出cal型中间相，大部分为单相性。另一方面，在喹喔啉环上含有长烷基链的化合物中，侧链密度的显着增加使材料具有六方柱状相（Col h）。在这些材料中，在偶氮苯系统上引入小的极性取代基（例如硝基或氯）可提高Col h的稳定性。烷基链间隔物的存在是负责降低熔点和室温山口ħ这些化合物中的某些观察到了相。Col