3-(4'-hydroxyphenyl)-(Z)-propenoic acid methyl ester | 61240-27-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(4'-hydroxyphenyl)-(Z)-propenoic acid methyl ester
• 英文别名: 4-hydroxy-cis-cinnamic acid methyl ester；cis-p-hydroxycinnamic acid methyl ester；methyl-3-(4-hydroxyphenyl)acrylate；cis-p-coumaric acid methyl ester；(Z)-methyl p-hydroxycinnamate；cis-methyl p-coumarate；methyl (2Z)-3-(4-hydroxyphenyl)acrylate；methyl (Z)-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 61240-27-5
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: NITWSHWHQAQBAW-DAXSKMNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  3-(4'-hydroxyphenyl)-(Z)-propenoic acid methyl ester 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以90%的产率得到对羟基苯丙酸甲酯
  参考文献：
  名称：

  普那普林的合成研究：普那普林类似物的全合成

  摘要：

  陶他普林1的合成类似物的合成已经完成。最终大环内酯的构建使用Keck大环内酯化反应完成。

  DOI：

  10.1016/j.tetlet.2005.06.145
• 作为产物：
  描述：

  4-香豆酸 在 硫酸 作用下， 以 乙腈 为溶剂， 反应 25.0h， 生成 3-(4'-hydroxyphenyl)-(Z)-propenoic acid methyl ester
  参考文献：
  名称：

  Mechanistic and stereochemical study of phenylpyruvate tautomerase

  摘要：

  A variety of substrates and potential enol/enolate mimics for the product/transition state of the enzyme phenylpyruvate tautomerase (E.C. 5.3.2.1) have been prepared and studied. Their stereostructures have been secured by a combination of NMR spectroscopy based on vicinal H-F and H-C coupling constants and X-ray crystallography. On the basis of the inhibition by stereoisomeric substituted cinnamates, it has been concluded that the enzyme produces the thermodynamically less stable (E) enol via a syn tautomerization transition state. Free energy profiles for the reaction suggest that vinyl fluorides act as product analogues. Because amide and dicarboxylate enolate mimics are relatively poor inhibitors of the enzyme, it is believed that an enolate is not involved in the tautomerization process.

  DOI：

  10.1021/ja00069a006

文献信息

• Synthesis of Phenols: Organophotoredox/Nickel Dual Catalytic Hydroxylation of Aryl Halides with Water
  作者：Liu Yang、Zhiyan Huang、Gang Li、Wei Zhang、Rui Cao、Chao Wang、Jianliang Xiao、Dong Xue

  DOI：10.1002/anie.201710698

  日期：2018.2.12

  A highly effective hydroxylation reaction of aryl halides with water under synergistic organophotoredox and nickel catalysis is reported. The OH group of the resulting phenols originates from water, following deprotonation facilitated by an intramolecular base group on the ligand. Significantly, aryl bromides as well as less reactive aryl chlorides served as effective substrates to afford phenols with

  报道了在协同的有机光氧化还原和镍催化下，芳基卤化物与水的高效羟基化反应。在配体上的分子内碱基促进去质子化之后，所得酚的OH基团起源于水。重要的是，芳基溴化物和反应性较低的芳基氯用作有效的底物，以提供具有广泛官能团的酚。不需要强大的无机碱或昂贵的贵金属催化剂，该方法可用于有效制备各种酚，并使多官能药学上相关的芳基卤化物羟基化。
• Wittig Reactions in Water Media Employing Stabilized Ylides with Aldehydes. Synthesis of α,β-Unsaturated Esters from Mixing Aldehydes, α-Bromoesters, and Ph₃P in Aqueous NaHCO₃
  作者：Amer El-Batta、Changchun Jiang、Wen Zhao、Robert Anness、Andrew L. Cooksy、Mikael Bergdahl

  DOI：10.1021/jo070665k

  日期：2007.7.1

  range of stabilized ylides and aldehydes. Despite sometimes poor solubility of the reactants, good chemical yields normally ranging from 80 to 98% and high E-selectivities (up to 99%) are achieved, and the rate of the reactions in water is unexpectedly accelerated. The efficiency of water as a medium in the Wittig reaction is compared to conventional organic solvents ranging from carbon tetrachloride

  事实证明，水是在多种稳定的乙炔和醛上进行维蒂希反应的有效介质。尽管有时反应物的溶解度较差，但通常可获得80-98 ％的良好化学收率和较高的E选择性（高达99％），并且在水中的反应速度出乎意料地加快了。将水作为Wittig反应介质的效率与常规有机溶剂（从四氯化碳到甲醇）进行了比较。当存在大量疏水性实体（例如芳香族，杂环芳香族甲醛和长链脂族醛与三苯基膦）时，维蒂希水溶液反应最有效。该Ë / ž维蒂希产物的β-异构体比例取决于电子接受/给体能力和存在于芳环中的取代基的位置。研究了添加剂（例如苯甲酸，LiCl和十二烷基硫酸钠（SDS））对Wittig反应的影响。Wittig反应也可以在酸性实体例如苯酚和羧酸的存在下进行。另外，脂族醛中的大α-取代基不会危害反应。还证明了醛的水合物可以直接在含水维蒂希反应中用作底物。Wittig水溶液的反应范围扩展到Ph 3的一锅混合物的24个例子碳酸氢钠溶液中的P
• Competing OH insertion and β-elimination in rhodium carbenoid reactions; synthesis of 2-alkoxy-3-arylpropanoates
  作者：Geoffrey G. Cox、David Haigh、Richard M. Hindley、David J. Miller、Christopher J. Moody

  DOI：10.1016/s0040-4039(00)76851-1

  日期：1994.5

  Rhodium(II) carboxylate catalysed decomposition of diazo esters 3 and 4 in the presence of alcohols or water results in formation of 2-alkoxy- or 2-hydroxy-3-arylpropanoates respectively by OH insertion in competition with cinnamates by elimination; the ratio of insertion to elimination is dramatically affected by the carboxylate ligand on rhodium. Use of methanol-d as the alcohol confirms that the

  在醇或水存在下，羧酸铑（II）催化重氮酯3和4分解，分别通过OH插入形成2-烷氧基-或2-羟基-3-芳基丙酸酯，并与肉桂酸酯竞争消除。铑上的羧酸盐配体极大地影响了插入与消除的比率。甲醇-d作为醇的使用证实了通过从初始烷氧基酯产物中消除而不会产生烯烃。
• Unravelling the Structural and Molecular Basis Responsible for the Anti-Biofilm Activity of Zosteric Acid
  作者：Cristina Cattò、Silvia Dell’Orto、Federica Villa、Stefania Villa、Arianna Gelain、Alberto Vitali、Valeria Marzano、Sara Baroni、Fabio Forlani、Francesca Cappitelli

  DOI：10.1371/journal.pone.0131519

  日期：——

  The natural compound zosteric acid, or p-(sulfoxy)cinnamic acid (ZA), is proposed as an alternative biocide-free agent suitable for preventive or integrative anti-biofilm approaches. Despite its potential, the lack of information concerning the structural and molecular mechanism of action involved in its anti-biofilm activity has limited efforts to generate more potent anti-biofilm strategies. In this study a 43-member library of small molecules based on ZA scaffold diversity was designed and screened against Escherichia coli to understand the structural requirements necessary for biofilm inhibition at sub-lethal concentrations. Considerations concerning the relationship between structure and anti-biofilm activity revealed that i) the para-sulfoxy ester group is not needed to exploit the anti-biofilm activity of the molecule, it is the cinnamic acid scaffold that is responsible for anti-biofilm performance; ii) the anti-biofilm activity of ZA derivatives depends on the presence of a carboxylate anion and, consequently, on its hydrogen-donating ability; iii) the conjugated aromatic system is instrumental to the anti-biofilm activities of ZA and its analogues. Using a protein pull-down approach, combined with mass spectrometry, the herein-defined active structure of ZA was matrix-immobilized, and was proved to interact with the E. coli NADH:quinone reductase, WrbA, suggesting a possible role of this protein in the biofilm formation process.

  天然化合物带状疱疹酸或对-（硫氧）肉桂酸（ZA）被认为是一种不含生物杀灭剂的替代药剂，适用于预防性或综合性抗生物膜方法。尽管ZA具有潜力，但由于缺乏有关其抗生物膜活性的结构和分子作用机制的信息，因此限制了开发更有效的抗生物膜策略的努力。在这项研究中，我们设计了一个由 43 个成员组成的基于ZA 支架多样性的小分子化合物库，并针对大肠杆菌进行了筛选，以了解在亚致死浓度下抑制生物膜所需的结构要求。对结构与抗生物膜活性之间关系的考虑表明：i) 利用分子的抗生物膜活性并不需要对位硫氧酯基团，肉桂酸支架才是抗生物膜性能的关键；ii) ZA 衍生物的抗生物膜活性取决于羧酸阴离子的存在，因此也取决于其供氢能力；iii) 共轭芳香系统对 ZA 及其类似物的抗生物膜活性至关重要。通过蛋白质牵引法和质谱法，ZA 的活性结构被基质固定，并被证明与大肠杆菌 NADH：醌还原酶 WrbA 相互作用，这表明该蛋白质可能在生物膜形成过程中发挥作用。
• Quinic acid derivatives from Pimpinella brachycarpa exert anti-neuroinflammatory activity in lipopolysaccharide-induced microglia
  作者：Seung Young Lee、Eunjung Moon、Sun Yeou Kim、Kang Ro Lee

  DOI：10.1016/j.bmcl.2013.01.115

  日期：2013.4

  Five new quinic acid derivatives (1-5), together with 10 known quinic acid derivatives (6-15), were isolated from the MeOH extract of Pimpinella brachycarpa (Umbelliferae). Their structures were established on the basis of spectroscopic analyses including extensive 2D NMR studies (COSY, HMQC and HMBC). Isolated compounds 1-15 were evaluated for their inhibitory activities on nitric oxide (NO) production in an activated murine microglial cell line. Compounds 2, 3, 8 and 11 significantly inhibited NO production without high cell toxicity in lipopolysaccharide (LPS)-activated BV-2 cells, a microglia cell line (IC50 = 4.66, 12.52, 9.04 and 12.11 mu M, respectively). (C) 2013 Elsevier Ltd. All rights reserved.