(E)-4-((4-methoxyphenyl)diazenyl)benzoic acid | 174023-08-6

• 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: (E)-4-((4-methoxyphenyl)diazenyl)benzoic acid
• 英文别名: 4-((4-methoxyphenyl)diazenyl)benzoic acid；4-((4-methoxyphenyl)azo)benzoic acid
• CAS: 174023-08-6
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: OVFHIXQDBHHUDN-FOCLMDBBSA-N

物化性质

• 沸点：
  458.2±25.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 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：
  0.07
• 拓扑面积：
  71.25
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-4-((4-methoxyphenyl)diazenyl)benzoic acid 在 lithium aluminium tetrahydride 、 草酰氯 、 硫酸 、 二甲基亚砜 作用下， 以 乙醚 为溶剂， 生成 (E)-4-(4-methoxyphenyldiazenyl)benzaldehyde
  参考文献：
  名称：

  偶氮苯卟啉

  摘要：

  已经合成了一系列共价连接的偶氮苯-卟啉衍生物，并研究了它们的光化学性质。卟啉组分的光化学基本不变，但是偶氮苯组分的光化学异构化不能被检测到。

  DOI：

  10.1016/0040-4039(95)02246-5
• 作为产物：
  描述：

  对氨基苯甲酸 在 盐酸 、 sodium hydride 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-4-((4-methoxyphenyl)diazenyl)benzoic acid
  参考文献：
  名称：

  偶氮苯卟啉

  摘要：

  已经合成了一系列共价连接的偶氮苯-卟啉衍生物，并研究了它们的光化学性质。卟啉组分的光化学基本不变，但是偶氮苯组分的光化学异构化不能被检测到。

  DOI：

  10.1016/0040-4039(95)02246-5

文献信息

• Mechanism of Alkaline Hydrolysis of Some HO-π-COOAr Acyl Derivatives
  作者：Giorgio Cevasco、Sergio Thea

  DOI：10.1021/jo990151o

  日期：1999.7.1

  To gain knowledge on the role played by the nature of the bridge interposed between hydroxyl and carbonyl groups in esters of the title type, in principle able to hydrolyze through dissociative pathways via the conjugate base of the substrate (E1cB mechanism), we have studied the alkaline hydrolyses of 2,4-dinitrophenyl esters in which the pi-system is a biphenyl, azobenzene, benzylideneaniline, or

  为了了解标题类型的酯中羟基和羰基之间插入的桥的本质所起的作用，原则上能够通过底物的共轭碱基通过解离途径进行水解（E1cB机理），我们研究了碱性水解2，4-二硝基苯酯，其中pi系统是联苯，偶氮苯，亚苄基苯胺或二苯乙烯骨架。动力学数据，例如反应性比较和Arrhenius参数，表明这些底物通过通常的缔合B（Ac）2机理发生反应。从结构和精力的角度讨论和解释了这一结果。数据表明，对于亚苄基氨基取代基（C（6）H（5）CH = N-），最合适的sigma（p）（）值是0.0。
• Structure–property relationships of photoresponsive inhibitors of the kinesin motor
  作者：Ammathnadu S. Amrutha、K. R. Sunil Kumar、Kazuya Matsuo、Nobuyuki Tamaoki

  DOI：10.1039/c6ob00951d

  日期：——

  A new, more efficient photoresponsive inhibitor (key) of kinesin (lock), for the complete ON/OFF switching of kinesin motor activity was developed.

  开发了一种新的、更高效的光响应性抑制剂（钥匙），用于完全打开/关闭肌动蛋白机动活动的抑制剂（锁）。
• Visible-Light-Controlled Histone Deacetylase Inhibitors for Targeted Cancer Therapy
  作者：Laia Josa-Culleré、Amadeu Llebaria

  DOI：10.1021/acs.jmedchem.2c01713

  日期：2023.2.9

  light by introducing o-halogen atoms into the azobenzene. Selected compounds decreased cell viability only under illumination in four different cancer cell lines. Overall, we present photoswitchable HDACis with optimized activation wavelengths, which inhibit enzyme activity and cell viability only upon illumination with visible light, contributing to the still limited toolbox of photoswitchable anticancer

  抗癌药物缺乏选择性限制了目前的化疗。光激活药物的活性可以通过外部光精确控制，可以使药物在肿瘤中发挥更局部的作用，从而减少副作用并提高疗效。在此，我们介绍了一系列光开关偶氮苯组蛋白脱乙酰酶抑制剂 (HDACis)，其活性可通过外部可见光控制。最初的 HDACis 在紫外光下异构化，在酶测定中，光照下的活性比黑暗中高 50 倍以上。然后通过引入o将这些化合物优化为对更具渗透性和危害性更小的绿光作出反应的化合物-卤素原子变成偶氮苯。选定的化合物仅在四种不同癌细胞系的光照下降低细胞活力。总的来说，我们提出了具有优化激活波长的光开关 HDACis，它仅在用可见光照射时才抑制酶活性和细胞活力，这有助于光开关抗癌药物的工具箱仍然有限。
• Thermal and Light Control of the Sol-Gel Phase Transition in Cholesterol-Based Organic Gels. Novel Helical Aggregation Modes As Detected by Circular Dichroism and Electron Microscopic Observation
  作者：Kazutaka Murata、Masayoshi Aoki、Tsuyoshi Suzuki、Takaaki Harada、Hirosuke Kawabata、Takashi Komori、Fumio Ohseto、Keiko Ueda、Seiji Shinkai

  DOI：10.1021/ja00094a023

  日期：1994.7

  Nineteen cholesterol derivatives containing a variety of azobenzene moieties coupled to C-3 of a steroidal moiety through an ester linkage were synthesized. We employed two different esterification methods by which cholesterol derivatives with the natural (S)-configuration at C-3 and those with the inverted (R)-configuration at C-3 were obtained (the latter derivatives are indicated by a prime). Among them, cholesterol derivatives bearing a p-alkoxyazobenzene moiety (2R and 2R') acted as excellent thermally-reversible gelators of various organic fluids, but the gelation ability is fairly different between 2R and 2R': 2R could gelatinize hydrocarbons such as n-hexane, n-octane, and toluene, halogen solvents such as 1,2-dichloroethane and dichloromethane, ether solvents such as diethyl ether and THF, and alcohols such as ethanol and I-butanol whereas 2R' could gelatinize ketones, methanol, and polysiloxanes. In general, the solubility of 2R' in apolar solvents is superior to that of 2R, so 2R is useful for gelation of apolar solvents whereas 2R' is useful for gelation of polar solvents. We found that the sol-gel phase transition is sensitively ''read-out'' by a change in the circular dichroism (CD) spectrum: the gel phase is CD-active whereas the sol phase is totally CD-silent. For example, the 2Me-1-butanol gel gave a positive exciton coupling band with (R)-chirality whereas the 2Et'-methanol gel gave a negative exciton coupling band with (S)-chirality. These results mean that dipoles in the azobenzene moiety are oriented in a clockwise (in (R)-chirality) or anticlockwise (in (S)-chirality) direction when they interact in the excited state. Strangely, we accidentally found that the CD sign of the gels prepared from 2Pr, 2Bu, and 3Me' (azobenzene-linked cholesterol derivative with p-NMe(2)) is frequently inverted. After careful examination of the gel preparation conditions, we found that inversion takes place only when the cooling speed is fast. The scanning electron microscopic studies established that gelators form three-dimensional networks with helical fibrils. Interestingly, we found that in the 3Me' gel prepared from cyclohexane the gel with (R)-chirality in CD possesses a right- handed helix whereas the gel with (S)-chirality in the CD possesses a left-handed helix. The sol-gel phase transition was also induced by photoresponsive cis-trans isomerism of the azobenzene moiety: the gel formed from the trans-isomer was efficiently converted to the sol when trans-to-cis isomerization was photochemically induced, and this process can be repeated reversibly. The photoinduced sol-gel phase transition was also ''read-out'' as a change in CD spectroscopy.
• A Redox Isomerization Strategy for Accessing Modular Azobenzene Photoswitches with Near Quantitative Bidirectional Photoconversion
  作者：Jie S. Zhu、Julio M. Larach、Robert J. Tombari、Phillip W. Gingrich、Stanley R. Bode、Jeremy R. Tuck、Hunter T. Warren、Jung-Ho Son、Whitney C. Duim、James C. Fettinger、Makhluf J. Haddadin、Dean J. Tantillo、Mark J. Kurth、David E. Olson

  DOI：10.1021/acs.orglett.9b03387

  日期：2019.11.1

  Photoswitches capable of accessing two geometric states are highly desirable, especially if their design is modular and incorporates a pharmacophore tethering site. We describe a redox isomerization strategy for synthesizing p-formylazobenzenes from p-nitrobenzyl alcohol. The resulting azo-aldehydes can be readily converted to photoswitchable compounds with excellent photophysical properties using simple hydrazide click chemistry. As a proof of principle, we synthesized a photoswitchable surfactant enabling the photocontrol of an emulsion with exceptionally high spatiotemporal precision.