4-(p'-methoxyphenylazo)pyridine | 20815-67-2

• 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-(p'-methoxyphenylazo)pyridine
• 英文别名: 4-(4'-methoxyphenylazo)pyridine；NoName_3894；(4-methoxyphenyl)-pyridin-4-yldiazene
• CAS: 20815-67-2
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: QAHXMHRIMFMINN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(p'-methoxyphenylazo)pyridine 在 硫酸 作用下， 以 水 为溶剂， 生成 4-(4-hydroxyphenylazo)pyridine
  参考文献：
  名称：

  Buncel, Erwin; Onyido, Ikenna, Canadian Journal of Chemistry, 1986, vol. 64, p. 2115 - 2126

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(4-hydroxyphenylazo)pyridine 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以81%的产率得到4-(p'-methoxyphenylazo)pyridine
  参考文献：
  名称：

  A photoswitchable bis-azo derivative with a high temporal resolution

  摘要：

  本文报道的新型光开关双偶氮衍生物表现出高达2×10⁸倍的时间分辨率，其两个构成光致变色团的热弛豫速率之间。

  DOI：

  10.1039/c4cc05331a

文献信息

• Studies of azo and azoxy dyestuffs-16
  作者：Erwin Buncel、Sam-Rok Keum

  DOI：10.1016/s0040-4020(01)91871-x

  日期：1983.1

  of pH, which provides clues to interpretation of the equilibria involved in this series. Further consideration of possible protolytic and tautomeric equilibria (Schemes 1–3) has allowed the various microscopic equilibrium constants to be assigned, the first instance in the hydroxyphenylazopyridine series. It is concluded that hydrazone tautomeric forms are not important in these systems. The equilibrium

  用分光光度法对标题化合物1和相关底物2-4所经历的蛋白水解平衡进行了研究。化合物1与两个宏观质子化的平衡常数（PK相关联一个1 = 7.73，PK一个1而化合物= 4.65）2，3和4是在每种情况下（单质子化的平衡的pK相关联一个2，= 6.31，pK值一3 = 6.31，pK a 4= 4.53）。化合物2和3表现出与pH相同的光谱行为，这为解释该系列中的平衡提供了线索。进一步考虑可能的蛋白水解和互变异构平衡（方案1-3），可以分配各种微观平衡常数，这是羟苯基偶氮吡啶系列中的第一个实例。结论是互变异构形式在这些系统中并不重要。中性（HA）和两性离子（AH±）形式之间的平衡1主要是对前侧，而4-羟基吡啶和4-吡啶酮之间的平衡有利于大大后者形式。根据结构和电子效应，对各种平衡常数进行了讨论。
• Three different mechanisms for azo-ether hydrolyses in aqueous acid
  作者：Robin A. Cox、Erwin Buncel

  DOI：10.1139/v2012-076

  日期：2012.10

  It has been shown recently that most ethers hydrolyze in aqueous acid media not by the traditional A1 or A2 process, but by a mechanism involving rate-determining proton transfer to the substrate, concerted with C–O bond cleavage. The reactions of azoethers are more complicated, because the azo group can be protonated in the acid reaction medium as well. This protonation has to be accounted for in the kinetic analysis. Often it simply ties up the substrate in an unreactive form; the hydrolysis reaction slows down as a result of the azo-protonated compound not being the reactant in the hydrolysis. However, there are other possibilities. If the ether group is suitably located in the substrate the azo-protonated compound can react with three water molecules (a “water wire”) in a fast reaction, and the alkoxy group is lost as a result. Depending on the acidity, in this mechanism either the initial three-water attack, or the breakup of the resulting intermediate, can be rate-determining, and both of these were observed. A third possibility is that ring protonation of suitable substrates can occur, giving delocalized carbocations that can form a hydrolysis product in subsequent fast reactions. Thus, three different hydrolysis mechanisms for azoethers in acidic media can be observed. Six azoethers were studied, one of which contained two methoxy groups. Both of these hydrolyzed, but by different mechanisms.

  最近的研究表明，大多数醚类化合物在水酸性介质中水解的机理不是传统的A1或A2过程，而是涉及速率决定性质子转移到底物，同时与C-O键裂解协同的机制。偶氮醚的反应更加复杂，因为偶氮基团在酸性反应介质中也可以质子化。这种质子化必须在动力学分析中加以考虑。通常情况下，它只是将底物束缚在不反应的形式中；由于偶氮质子化化合物不是水解反应的反应物，水解反应因此而减慢。然而，还有其他可能性。如果醚基团在底物中位置适当，偶氮质子化化合物可以与三个水分子（“水线”）快速反应，从而失去烷氧基团。在这种机制中，取决于酸度，初始的三水攻击或所得中间体的分解可以是速率决定性的，这两种情况都被观察到。第三种可能性是，适当底物的环质子化可以发生，产生可以在随后的快速反应中形成水解产物的离域碳阳离子。因此，在酸性介质中可以观察到偶氮醚的三种不同的水解机制。研究了六种偶氮醚，其中一种含有两个甲氧基团。这两种都被水解了，但是通过不同的机制。
• Heteroaromatic Azo-activated Nucleophilic Substitutions. The Reaction of 4-(p-Methoxyphenylazo)pyridinium Methiodide with Piperidine in Dimethyl Sulphoxide
  作者：Ikenna Onyido、Collins I. Ubochi

  DOI：10.3987/r-1987-02-0313

  日期：——
• Cytotoxicity of η-areneruthenium-based molecules to glioblastoma cells and their recognition by multidrug ABC transporters
  作者：Jaqueline Pazinato、Otávio M. Cruz、Karine P. Naidek、Amanda R.A. Pires、Eduard Westphal、Hugo Gallardo、Hélène Baubichon-Cortay、Maria E.M. Rocha、Glaucia R. Martinez、Sheila M.B. Winnischofer、Attilio Di Pietro、Herbert Winnischofer

  DOI：10.1016/j.ejmech.2018.02.026

  日期：2018.3

  A new series of amphiphilic eta(6)-areneruthenium(II) compounds containing phenylazo ligands (group I: compounds la, 1b, 2a and 2b) and phenyloxadiazole ligands (group II: compounds 3a, 3b, 4a and 4b) were synthesized and characterized for their anti-glioblastoma activity. The effects of the amphiphilic eta(6)-areneruthenium(II) complexes on the viability of three human glioblastoma cell lines, U251, U87MG and T98G, were evaluated. The azo-derivative ruthenium complexes (group I) showed high cytotoxicity to all cell lines, whilst most oxadiazole-derivative complexes (group II) were less cytotoxic, except for compound 4a. The cationic complexes 2a, 2b and 4b were more cytotoxic than the neutral complexes. Compounds 2a and 2b caused a significant reduction in the percentage of cells in the G0/G1 phase, with concomitant increases in the G2/M phase and fragmented DNA in the T98G cell line. The eta(6)-areneruthenium(11) compounds were also tested in cell lines that overexpress the multidrug ABC transporters P-gp, MRP1 and ABCG2. Compounds 2b and 4a were substrates for the P-gp protein, with resistance indexes of 8.6 and 1.9, respectively. Compound 2b was also a substrate for ABCG2 and MRP1 proteins, with lower resistance indexes (1.8 and 1.6, respectively). The contribution of multidrug ABC transporters to the cytotoxicity of compound 2b in T98G cells was evidenced, since verapamil (a characteristic inhibitor of MRP1) increased the cytotoxicity of compound 2b at concentrations up to 20 mu mol L-1, whilst GP120918 and Ko143 (specific inhibitors of P-gp and ABCG2, respectively) had no significant effect. In addition, we showed that compound 2b interacts with glutathione (GSH), which could explain its cellular efflux by MRP1. Our results showed that the amphiphilic eta(6)-areneruthenium(II) complexes are promising anti-glioblastoma compounds, especially compound 2b, which was cytotoxic for all three cell lines, although it is transported by the three main multidrug ABC transporters. (C) 2018 Elsevier Masson SAS. All rights reserved.
• SEALANT, METHOD FOR PRODUCING BEZEL-LESS LIQUID CRYSTAL DISPLAY, AND BEZEL-LESS LIQUID CRYSTAL DISPLAY PRODUCED BY THE SAME
  申请人：BOE TECHNOLOGY GROUP CO., LTD.

  公开号：US20180113338A1

  公开（公告）日：2018-04-26

  A sealant ( 9 ), a method for producing bezel-less liquid crystal display, and a bezel-less liquid crystal display produced by the same. The sealant ( 9 ) comprises: an azopyridine derivative represented by the structural formula (1); one or more of polyvinyl alcohol and ethylene-vinyl acetate copolymer; and a solvent, wherein m in the structural formula (1) is an integer of 8-20; and a mass ratio of the azopyridine derivative to the one or more of polyvinyl alcohol and ethylene-vinyl acetate copolymer is 1/99-15/85. A color filter substrate ( 6 ) and an array substrate ( 7 ) of a liquid crystal display are bound under the irradiation of ultraviolet light by using the photothermal effect and the binding property of a mixture of an azopyridine derivative and one or more of polyvinyl alcohol and ethylene-vinyl acetate copolymer, while the bezel of the liquid crystal display panel is not occupied, so as to obtain a bezel-less liquid crystal display.