4-[(6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]benzoic acid | 788-24-9

• 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-[(6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]benzoic acid
• 英文别名: 4-(2-hydroxybenzylideneamino)benzoic acid；N-(4-carboxyphenyl)salicylideneimine；N-salicylidene-p-carboxyaniline；HBBA；N-(p-Benzoesaeure)salicylaldimin
• CAS: 788-24-9
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: CZNXQJHAMQNIHB-OQLLNIDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 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：
  69.89
• 氢给体数：
  2.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  铁粉 、 4-[(6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]benzoic acid 以 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  基于席夫碱及其Hirshfeld表面和DFT研究开发用于检测Fe 3+离子的开关选择性荧光传感器

  摘要：

  在此，合成了席夫碱，4-（2-羟基亚苄基氨基）苯甲酸（HBBA），并通过FT-IR，1 H NMR和单晶X射线表征。使用DFT方法制备的结构计算出的几何参数与实验观察值非常吻合。Hirshfeld表面分析对晶体结构进行了研究，以探索分子中的各种分子内相互作用。为了支持电荷转移，使用DFT方法计算了带隙和分子静电势。使用NBO分析探索了供体（i）和受体（j）的超共轭相互作用和电子密度。光物理研究揭示了吸收曲线对p的依赖性。H的媒介。使用DFT方法计算的热力学性质显示出热容（C），熵（S）和焓变（H）与温度之间的相关性。该传感器对Fe 3+离子具有特异性，在添加EDTA后其荧光特性具有关断响应和可逆性。该方法成功应用于水样中Fe 3+的实时检测，具有较高的准确度。对于已开发的传感器，观察到的检出限低于饮用水的USEPA指南（5.37μM）。

  DOI：

  10.1016/j.molliq.2019.111814
• 作为产物：
  描述：

  水杨醛 、 对氨基苯甲酸 以 乙醇 为溶剂， 反应 5.0h， 生成 4-[(6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]benzoic acid
  参考文献：
  名称：

  固体氩气中N-水杨基-对羧基苯胺的结构和光化学

  摘要：

  红外矩阵隔离光谱法和DFT / B3LYP / 6-311 ++ G（d，p）计算已用于表征N-水杨基-对-羧基苯胺（SCA）的烯醇亚胺和酮胺互变异构体的构象空间以它们的E和Z异构形式存在。在氩气基质（15 K）中分离出SCA的单体，该基质显示仅包含该化合物的E-烯醇异构体的最稳定构象体。然后将基质分离的E-烯醇进行原位处理UV照射（由激光/ MOPO系统提供的λ= 335； 345 nm，或由Hg（Xe）宽带光源提供的λ> 235 nm），以及通过红外光谱探测的光诱导过程。观察到两个光反应通道，其分支比为〜1：1，分别对应于E-烯醇→ Z-烯醇异构化和E-烯醇→ E-酮互变异构。发现这两种方法都是相当有效的，仅在宽带照射1分钟后几乎完全消耗了反应物。在Z-烯醇构象的光生物质中的鉴定与仅由E- to- Z反应的反应物不同异构化表明该构象异构体的初始光产生，随后逐渐降解为最低能量的Z-烯醇构

  DOI：

  10.1021/acs.jpca.5b06516

文献信息

• Solid state photochromism and thermochromism of two related N-salicylidene anilines
  作者：Mihaela Avadanei、Vasile Cozan、Sergiu Shova、José António Paixão

  DOI：10.1016/j.chemphys.2014.10.007

  日期：2014.11

  The crystalline structure and optical properties of N-salicylidene-p-cyanoaniline and N-salicylidene-p-carboxyaniline were investigated in solid state (microcrystalline powder), with the purpose to connect the effects of substitution and crystal packing with their optical properties. Diffuse reflectance and fluorescence spectroscopy were used to study the absorption and emission properties upon photoirradiation and cooling down to the liquid nitrogen temperature. The Stokes-shifted fluorescence, with a quantum yield of about 10(-2)-10(-1), is given by the tautomeric cis-keto species formed as a result of the excited state intramolecular proton transfer from the initial enol structure. Despite their similar geometrical parameters, only SA-COOH is photochromic, which is in contradiction with literature. On the other side, the thermochromism is especially strong at SA-CN. The study shows the behavior of SA-CN similar to that of a classical anil, while SA-COOH presents interesting features that contradict the presumed behavior based only on its supramolecular structure. (c) 2014 Elsevier B.V. All rights reserved.
• Spectral regression and correlation coefficients of some benzaldimines and salicylaldimines in different solvents
  作者：Hassan H. Hammud、Amer Ghannoum、Mamdouh S. Masoud

  DOI：10.1016/j.saa.2005.04.020

  日期：2006.2

  Sixteen Schiff bases obtained from the condensation of benzaldehyde or salicylaldehyde with various amines (aniline, 4-carboxyaniline, phenlhydrazine, 2,4-dinitrophenylhydrazine, ethylenediamine, hydrazine, o-phenylenediamine and 2,6-pyridinediamine) are studied with UV-vis spectroscopy to observe the effect of solvents, substituents and other structural factors on the spectra. The bands involving different electronic transitions are interpreted. Computerized analysis and multiple regression techniques were applied to calculate the regression and correlation coefficients based on the equation that relates peak position to the solvent parameters that depend on the H-bonding ability, refractive index and dielectric constant of solvents. (c) 2005 Elsevier B.V. All rights reserved.
• SALTS OF PAROXETINE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1091958A1

  公开（公告）日：2001-04-18
• NEW 2-PYRIMIDINYLOXY-N-ARYL-BENZYLAMINE DERIVATIVES, THEIR PROCESSES AND USES
  申请人：SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY, CHINESE ACADEMY OF SCIENCES

  公开号：EP1327629B1

  公开（公告）日：2007-11-14
• METHODS AND COMPOSITIONS OF TRAIL-DEATH RECEPTOR AGONISTS/ACTIVATORS
  申请人：Srivastava Rakesh K.

  公开号：US20080214547A1

  公开（公告）日：2008-09-04

  This invention describes a series of methods and compositions for prevention and treatment of diseases such as cancer. One aspect of the invention describes small molecule-based drugs that can be used to bind to death receptors TRAIL-R1/DR4 and/or TRAIL-R2/DR5 and induce apoptosis in cancer cells, while sparing normal cells. The invention also describes TRAIL Death Receptor Agonists/Activators (DRAs) and their uses, such as the induction of apoptosis through caspase-8 and caspase-3 activation. The present invention also describes the methods of treating cancers, such as breast, prostate, colon, pancreatic, ovarian, lung, and brain cancers, leukemia, lymphoma, multiple myeloma, and mesothelioma, using DRAs either as single-agent treatments, or in combination with other therapies.