4-[4-(cyanophenyl)azo]phenol | 26029-68-5

• 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-[4-(cyanophenyl)azo]phenol
• 英文别名: 4-hydroxy-4'-cyanoazobenzene；4-cyano-4'-hydroxyazobenzene；4-(4-hydroxyphenylazo)benzonitrile；4-((4-hydroxyphenyl)diazenyl)benzonitrile；4-Cyano-4'-hydroxy-azobenzol；4-(4-Cyanophenylazo)phenol；4-[(4-hydroxyphenyl)diazenyl]benzonitrile
• CAS: 26029-68-5
• 化学式: C₁₃H₉N₃O
• 分子量: 223.234
• InChiKey: HKRIZVYPOGYCLC-UHFFFAOYSA-N

物化性质

• 熔点：
  194-196 °C(Solv: isopropanol (67-63-0))
• 沸点：
  457.4±30.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[4-(cyanophenyl)azo]phenol 在 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.5h， 生成 4-(10-acryloyloxydecyloxy)-4'-phenylazobenzonitrile
  参考文献：
  名称：

  Self-assembly of azobenzene based side-chain liquid crystalline polymer and n-alkyloxybenzoic acids

  摘要：

  通过超分子组装两种介晶成分，即聚[4-（10-丙烯酰氧基癸氧基）-4′-苯基偶氮苯甲腈]（P10）和4-烷氧基苯甲酸（A7-A12），制备了液晶吊坠聚合物复合物。羧酸和氰基之间的氢键起到了分子桥的作用。这些聚合物复合物表现出了稳定且外消旋的液晶态。通过对前体、单体和聚合物的1H-NMR和13C-NMR光谱分析进行了分析。通过FT-IR光谱学研究了聚合物复合物（P10-A7到P10-A12）中的氢键相互作用。通过差示扫描量热法和偏振光学显微镜分别研究了热行为和纹理分析。

  DOI：

  10.1007/s12039-011-0083-6
• 作为产物：
  描述：

  对氨基苯腈 在 Oxone 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 4-[4-(cyanophenyl)azo]phenol
  参考文献：
  名称：

  Structure requirements for anaerobe processing of azo compounds: Implications for prodrug design

  摘要：

  This Letter generalizes the metabolism of the azo class of compounds by Clostridium perfringens, an anaerobe found in the human colon. A recently reported 5-aminosalicylic acid-based prednisolone prodrug was shown to release the drug when incubated with the bacteria, while the para-aminobenzoic acid (PABA) based analogue did not. Instead, it showed a new HPLC peak with a relatively close retention time to the parent which was identified by LCMS as the partially reduced hydrazine product. This Letter investigates azoreduction across a panel of substrates with varying degrees of electronic and steric similarity to the PABA-based compound. Azo compounds with an electron donating group on the azo-containing aromatic ring showed immediate disproportionation to their parent amines without any detection of hydrazine intermediates by HPLC. Compounds containing only electron withdrawing groups are partially and reversibly reduced to produce a stable detectable hydrazine. They do not disproportionate to their parent amines, but regenerate the parent azo compound. This incomplete reduction is relevant to the design of azo-based prodrugs and the toxicology of azo-based dyes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.014

文献信息

• Fluorine-substituted azobenzene destabilizes polar form of optically switchable fulgimide unit in copolymer system
  作者：Saravanan Chinnusamy、Kannan Palaninathan

  DOI：10.1002/pola.23926

  日期：2010.4.1

  substituted azobenzene copolymers. Similarly, fluorescence pattern of F‐co‐FL by UV irradiation exhibited emission intensity slowly increased to certain level then decreases with two new emissions at 430 and 480 nm attributed to terminal position of fluorine atom on azobenzene destabilizes polar form (C‐form) fulgimide unit in the copolymer. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 1565–1578

  合成了氟甲酰亚胺和侧基均聚/共聚甲基丙烯酸酯中偶氮苯末端位置的取代基的各种尺寸和电子性质。差示扫描量热分析表明该均聚物具有Ç -形式俘精酰亚胺单元表现出更高的Ť米比的Ë -形式的均聚物和揭示Ç -形式是高度有序的。热稳定性表明，具有给电子取代基的偶氮苯均聚物比吸电子取代基具有更高的热稳定性。偏振光学显微镜观察揭示了均聚物，即NI，CY，FL，ME和T-ME在它们的T m和T i之间表现出液晶中间相。通过紫外可见光谱和荧光光谱研究了均聚物/共聚物的光学性质。紫外-可见光谱显示在F- co- FL中C形符ful酰亚胺的吸收约为482 nm，比取代的偶氮苯共聚物的C形要小40 nm 。同样，通过紫外线辐照的F- co- FL的荧光模式显示出发射强度缓慢增加到一定水平，然后随着430和480 nm处的两个新发射而降低，这归因于偶氮苯上氟原子的末端位置使极性形式不稳定（C共聚物中的形式）fulgimide单元。©2010
• Optimization of the Azobenzene Scaffold for Reductive Cleavage by Dithionite; Development of an Azobenzene Cleavable Linker for Proteomic Applications
  作者：Geoffray Leriche、Ghyslain Budin、Laurent Brino、Alain Wagner

  DOI：10.1002/ejoc.201000546

  日期：——

  henylazo)benzoic acid (HAZA) scaffold, the orthogonally protected difunctional azo–arene cleavable linker 26 was designed and synthesized. Selective linker deprotection and derivatization was performed by introducing an alkyne reactive group and a biotin affinity tag. This optimized azo–arene cleavable linker led to a total cleavage in less than 10 s with only 1 mM dithionite. Similar results were

  在本文中，我们进行了广泛的反应性研究，以确定有利于连二亚硫酸盐引发的偶氮芳烃基团还原裂解的关键结构特征。我们的逐步研究允许鉴定在缺电子芳烃的邻位带有羧酸的高反应性偶氮芳烃结构 25 和作为富电子芳烃的邻位-O-烷基间苯二酚。基于这种 2-(2'-烷氧基-4'-羟基苯基偶氮)苯甲酸 (HAZA) 支架，设计并合成了正交保护的双功能偶氮芳烃可裂解接头 26。通过引入炔反应基团和生物素亲和标签来进行选择性接头脱保护和衍生化。这种优化的偶氮芳烃可裂解接头导致在不到 10 秒内完全裂解，仅含 1 mM 连二亚硫酸盐。
• Photoresponsive polymers and block copolymers by molecular recognition based on multiple hydrogen bonds
  作者：Alberto Concellón、Eva Blasco、Milagros Piñol、Luis Oriol、Isabel Díez、Cristina Berges、Carlos Sánchez-Somolinos、Rafael Alcalá

  DOI：10.1002/pola.27373

  日期：2014.11.15

  group was synthesized and polymerized via RAFT polymerization to prepare homopolymethacrylates (PDAP) and diblock copolymers combined with a poly(methyl methacrylate) block (PMMA‐b‐PDAP). These polymers can be easily complexed with azobenzene chromophores having thymine (tAZO) or carboxylic groups with a dendritic structure (dAZO), which can form either three or two hydrogen bonds with the DAP groups, respectively

  合成了一种新的含2,6-二酰基氨基吡啶（DAP）基团的甲基丙烯酸酯，并通过RAFT聚合进行了聚合，以制备均聚甲基丙烯酸酯（PDAP）和与聚甲基丙烯酸甲酯嵌段（PMMA- b‐PDAP）。这些聚合物可以容易地与具有胸腺嘧啶（tAZO）或具有树突结构的羧基（dAZO）的偶氮苯生色团络合，后者可以分别与DAP基团形成三个或两个氢键。超分子聚合物通过光谱技术，光学显微镜，TGA和DSC进行表征。具有dAZO的超分子聚合物和嵌段共聚物表现出介晶性能，而具有tAZO的超分子聚合物和嵌段共聚物是非晶态材料。还研究了超分子聚合物对线偏振光照射的响应，发现尽管在包含树枝状发色团dAZO的聚合物中获得了更高的双折射和二向色性值，但在所有材料中均可以光诱导出稳定的光学各向异性。©2014 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学2014，52，3173-3184
• Synthesis, characterization, and photoresponsive behavior of a series of azobenzene-containing side-chain poly(ether sulfone)s with various lengths of flexible spacers
  作者：Yuxuan Zhang、Songhao Pei、Yongpeng Wang、Zengduo Cui、Na Li、Ye Zhu、Haibo Zhang、Zhenhua Jiang

  DOI：10.1016/j.dyepig.2013.08.004

  日期：2013.12

  A series of azobenzene-containing side-chain poly(ether sulfone)s (azo-PES) with various spacer lengths (2, 6 or 12 methylene units) were successfully synthesized via a nucleophilic substitution grafting reaction between poly(ether sulfone)s with hydroxylphenyl side groups and azobenzene monomers. Their chemical structures and properties were characterized by means of IR, UV–vis and 1H NMR. These azo-polymers

  通过聚（醚砜）与聚（醚砜）之间的亲核取代接枝反应成功地合成了一系列具有不同间隔长度（2个，6个或12个亚甲基单元）的含偶氮侧链聚（醚砜）（偶氮PES）。羟苯基侧基和偶氮苯单体。通过IR，UV-vis和1对它们的化学结构和性质进行了表征。1 H NMR。这些偶氮聚合物在玻璃化转变温度和119°C和347°C以上的5％失重温度下表现出良好的热稳定性。光异构化实验的结果表明，具有更长间隔基的偶氮-PES聚合物对应于更高的光异构化速率。在用532 nm掺钕钇铝石榴石（Nd：YAG）激光束照射时，它们呈现出的双折射残余值大于双折射饱和值的82％，表明光诱导取向的良好稳定性。在几次刻写-擦除-刻写序列循环之后，未观察到疲劳现象。
• Light-controllable reflection wavelength of blue phase liquid crystals doped with azobenzene-dimers
  作者：Xingwu Chen、Ling Wang、Chenyue Li、Jiumei Xiao、Hangjun Ding、Xin Liu、Xiaoguang Zhang、Wanli He、Huai Yang

  DOI：10.1039/c3cc46117c

  日期：——

  A new series of azobenzene-dimers were synthesized and doped into the blue phase liquid crystals to broaden the temperature range of BPs. It is found that not only can the reflection wavelength of BPI be reversibly controlled but BPI can also be transformed into the cholesteric phase owing to isomerization of azobenzene induced by light.

  新合成的一系列偶氮苯二聚体被掺入蓝相液晶中，以扩展BPs的温度范围。研究发现，不仅可以可逆地控制BPI的反射波长，而且由于光诱导的偶氮苯异构化作用，BPI还可以转变为胆甾相。