4'-methoxy-trans-stilbene-4-carboxylic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4'-methoxy-trans-stilbene-4-carboxylic acid
• 英文别名: 4-((E)-4-methoxystyryl)benzoic acid；4-[(E)-2-(4-methoxyphenyl)ethenyl]benzoic acid
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: NZVNHHANLDHTKQ-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4'-methoxy-trans-stilbene-4-carboxylic acid 在 甲基磺酰氯 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (E)-2-(4-(4-methoxystyryl)phenyl)-5-phenyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Small-Molecule Inhibitors of 25-Hydroxyvitamin D-24-Hydroxylase (CYP24A1): Synthesis and Biological Evaluation

  摘要：

  The synthesis of imidazole styrylbenzamide, tert-butyl styryl-imidazole, and tert-butyl styrylsulfonate derivatives is described. Evaluation of binding affinity and inhibitory activity against CYP24A1 identified the imidazole styrylbenzamides as potent inhibitors of CYP24A1, having selectivity with respect to CYP27B1 comparable with or greater than that of the standard ketoconazole. Further evaluation of the 3,5-dimethoxy and 3,4,5-trimethoxy derivatives in chronic lymphocytic leukemia cells revealed that co-treatment of 1 alpha,25-dihydroxyvitamin D-3 plus inhibitor coordinately upregulated GADD45 alpha and CDKN1A. Docking experiments on the inhibitors in the CYP24A1 enzyme active site suggest the compounds reach the active site through the vitamin D access tunnel and are exposed to multiple hydrophobic residues. The imidazole styrylbenzamides are optimally positioned to allow interaction of the imidazole with the heme, and, in the case of the methoxy derivatives, a hydrogen bond between the 3-methoxy group and Gln82 stabilizes the molecule in a favorable active conformation.

  DOI：

  10.1021/jm5009314
• 作为产物：
  描述：

  对甲基苯甲酸甲酯 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 二氯甲烷 、 xylene 为溶剂， 反应 0.08h， 生成 4'-methoxy-trans-stilbene-4-carboxylic acid
  参考文献：
  名称：

  Structure of Aggregates of trans-4-Alkoxy-4‘-carboxystilbenes in the Solid State and in Microheterogeneous Media. A Link between the “Unit Aggregate” and Extended Arrays

  摘要：

  Crystals of three 4-alkoxy-4'-carboxy trans-stilbene (ACS) derivatives and a crystal of 4-methoxy-4'-methanoate trans-stilbene have been shown to have structures in which the amphiphilic aromatics are arranged in layers remarkably similar to deposited Langmuir-Blodgett multilayer assemblies. Within each layer there is either a glide or pseudoglide (or herringbone) arrangement of the chromophores very similar to that deduced from physical properties and simulations for structurally related stilbene, azobenzene, and tolan amphiphiles in microheterogeneous media, solution, and Langmuir-Blodgett (LB) films. The fluorescence of the crystals is very similar to that associated with LB films of a water-insoluble amphiphilic ACS that is associated with the aggregate. An analysis of the crystal structure indicates that energetically favorable aromatic-aromatic (edge-face) interaction determines the packing within a layer.

  DOI：

  10.1021/jp962440b

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。
• Luminescent supramolecular assemblies based on hydrogen­bonded complexes of stilbenecarboxylic acids and dithieno[3,2­b:2′,3′­d]thiophene­2­carboxylic acids with a tris(imidazoline) base
  作者：Frank Osterod、Lars Peters、Arno Kraft、Takeshi Sano、John J. Morrison、Neil Feeder、Andrew B. Holmes

  DOI：10.1039/b009406o

  日期：——

  The synthesis of a number of stilbenecarboxylic acids, tetrazolylstilbenes and dithieno[3,2-b:2′,3′-d]thiophene-2-carboxylic acids is reported. These organic acids form non-covalent complexes with an imidazoline base, 1,3,5-tris(4,5-dihydroimidazol-2-yl)benzene 13. Two X-ray crystal structures confirm hydrogen bonds between carboxylate ligands and meta-positioned protonated imidazoline groups. The complexes possess a surprisingly flat disk-like shape with various close contacts between adjacent molecules. Most stilbene and dithieno[3,2-b:2′,3′-d]thiophene derivatives show strong blue or blue–green photoluminescence in solution, whereas fluorescence in the solid state is almost completely quenched.

  报道了一系列芪类羧酸、四唑基芪类化合物以及二噻吩[3,2-b:2′,3′-d]噻吩-2-羧酸的合成。这些有机酸与咪唑啉碱基，即1,3,5-三(4,5-二氢咪唑-2-基)苯13形成了非共价复合物。两个X射线晶体结构证实了羧酸盐配体与间位质子化的咪唑啉基团之间存在氢键。这些复合物具有出乎意料的扁平盘状形态，相邻分子之间存在多种紧密接触。大多数芪类和二噻吩[3,2-b:2′,3′-d]噻吩衍生物在溶液中表现出强烈的蓝色或蓝绿色光致发光，而在固态下荧光几乎完全淬灭。
• Liquid crystalline polyesters, their composition, and their uses
  申请人：NIPPON OIL CO., LTD.

  公开号：EP0905164A2

  公开（公告）日：1999-03-31

  There are provided liquid crystalline polyesters comprising 4'-hydroxy-4-stilbenecarboxylic acid type units, dicarboxylic acid units acting as a mesogen such as 4,4'-stilbenecarboxylic acid and catechol units as essential ingredients, and a liquid crystalline polyester composition comprising said polyesters and optically active liquid crystalline polyesters consisting essentially of 4,4'-stilbenedicarboxylic acid type units and aliphatic diol units having asymmetric carbons.

  提供了由 4'-羟基-4-二苯甲酸型单元、作为中间体的二羧酸单元（如 4,4'-二苯甲酸和邻苯二酚单元）作为基本成分组成的液晶聚酯，以及由上述聚酯和主要由 4,4'-二苯甲酸型单元和具有不对称碳原子的脂肪族二元醇单元组成的光学活性液晶聚酯组成的液晶聚酯组合物。
• Alkoxy/halostyryl benzoic acids: Synthesis, crystal structure, and study of mesomorphic and photophysical properties
  作者：Khushi Muhammad、M. Khawar Rauf、M. Nawaz Tahir、Shahid Hameed

  DOI：10.1080/15421406.2017.1328215

  日期：2017.6.13

  Alkoxy/halostyrylbenzoic acids were synthesized and evaluated for their mesomorphic and photophysical properties. The trans geometry of the molecules was established by the presence of large coupling constants in H-1-NMR spectra and confirmed further by X-ray diffraction (XRD) analysis of two of the compounds. The straight-chain acids were found fairly stable showing first sign of decomposition above 290 degrees C. The enantiotropic mesophases could only be studied in acids with seven or more methylene groups in the alkoxy chain. Textures of nematic and smectic phases were exhibited by these acids under polarizing optical microscope. Photophysical behavior of the compounds in solution was also investigated.
• Liquid crystalline polyester compositions and their uses
  申请人：Nippon Mitsubishi Oil Corporation

  公开号：EP0905164B1

  公开（公告）日：2006-05-03