4-((3,5-dimethoxyphenyl)diazenyl)phenol | 1393556-44-9

• 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-((3,5-dimethoxyphenyl)diazenyl)phenol
• CAS: 1393556-44-9
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: OBNOEIMWOLWCPS-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  63.41
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-((3,5-dimethoxyphenyl)diazenyl)phenol 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 14.05h， 生成 4-((3,5-dimethoxyphenyl)diazenyl)phenol
  参考文献：
  名称：

  使用光开关抑制剂对 F1 Fo -ATP 合酶进行可逆光学控制

  摘要：

  F1Fo-ATP 合酶是自然界中研究最好的大分子机器之一。它可以被一系列小分子抑制，其中包括多酚、白藜芦醇和 piceatannol。在这里，我们介绍了 ATP 合酶的光开关抑制剂，称为 PIAS，它们是从这些多酚合成衍生而来的。它们可用于通过光可逆地控制纯化酵母解脂耶氏酵母 ATP 合酶的酶活性。我们的实验表明，PIAS 与 ATP 合酶 F1 复合体中的反式多酚结合到相同的位点，但它们不以顺式形式结合。PIAS 可以成为在各种生化和生物技术应用中对 ATP 合酶进行光学精确控制的有用工具。

  DOI：

  10.1002/1873-3468.12958
• 作为产物：
  描述：

  3,5-二羟基苯甲酸甲酯 在 盐酸 、 叠氮磷酸二苯酯 、 potassium carbonate 、 三乙胺 、 苯甲酸 、 sodium hydroxide 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 6.5h， 生成 4-((3,5-dimethoxyphenyl)diazenyl)phenol
  参考文献：
  名称：

  Synthesis of novel azo-resveratrol, azo-oxyresveratrol and their derivatives as potent tyrosinase inhibitors

  摘要：

  Ten azo compounds including azo-resveratrol (5) and azo-oxyresveratrol (9) were synthesized using a modified Curtius rearrangement and diazotization followed by coupling reactions with various phenolic analogs. All synthesized compounds were evaluated for their mushroom tyrosinase inhibitory activity. Compounds 4 and 5 exhibited high tyrosinase inhibitory activity (56.25% and 72.75% at 50 mu M, respectively). The results of mushroom tyrosinase inhibition assays indicate that the 4-hydroxyphenyl moiety is essential for high inhibition and that 3,5-dihydroxyphenyl and 3,5-dimethoxyphenyl derivatives are better for tyrosinase inhibition than 2,5-dimethoxyphenyl derivatives. Particularly, introduction of hydroxyl or methoxy group into the 4-hydroxyphenyl moiety diminished or significantly reduced mushroom tryosinase inhibition. Among the synthesized azo compounds, azo-resveratrol (5) showed the most potent mushroom tyrosinase inhibition with an IC50 value of IC50 = 36.28 +/- 0.72 mu M, comparable to that of resveratrol, a well-known tyrosinase inhibitor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.050

文献信息

• Synthesis and switching properties of new derivatives of azoresveratrol
  作者：Jérôme Berthet、Laurence Agouridas、Siyao Chen、Hassan Allouchi、Patricia Melnyk、Benoît Champagne、Stéphanie Delbaere

  DOI：10.1016/j.dyepig.2019.107666

  日期：2019.12

  The synthesis and response upon light irradiation of azoresveratrol and six derivatives are reported. While UV irradiation of para-hydroxy trans compounds leads to thermally unstable cis isomers, the para-methoxy and the para-phosphoric ester substituents result in reaching a high conversion and increasing the thermal stability. In addition, the phosphoric ester azo derivative presents similar properties

  报道了偶氮白藜芦醇和六种衍生物的合成和光照射后的响应。虽然紫外线照射对羟基反式化合物会导致热不稳定的顺式异构体，但是对甲氧基和对磷酸酯取代基会导致高转化率并提高热稳定性。另外，磷酸酯偶氮衍生物在有机和水溶液中具有相似的性能，为生物学应用开辟了道路。
• Meta-Substituted Asymmetric Azobenzenes: Insights into Structure–Property Relationship
  作者：Anna Laura Sanna、Tatiana Pachova、Alessandra Catellani、Arrigo Calzolari、Giuseppe Sforazzini

  DOI：10.3390/molecules29091929

  日期：——

  This article presents a comprehensive investigation into the functionalization of methoxyphenylazobenzene using electron-directing groups located at the meta position relative to the azo group. Spectroscopic analysis of meta-functionalized azobenzenes reveals that the incorporation of electron-withdrawing units significantly influences the absorption spectra of both E and Z isomers, while electron-donating functionalities lead to more subtle changes. The thermal relaxation process from Z to E result in almost twice as prolonged for electron-withdrawing functionalized azobenzenes compared to their electron-rich counterparts. Computational analysis contributes a theoretical understanding of the electronic structure and properties of meta-substituted azobenzenes. This combined approach, integrating experimental and computational techniques, yields significant insights into the structure–property relationship of meta-substituted asymmetrical phenolazobenzenes.