(E)-3-(2,4-二羟基苯基)丙烯酸乙酯 | 149542-04-1

• 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
• 中文名称: (E)-3-(2,4-二羟基苯基)丙烯酸乙酯
• 英文名称: (E)-ethyl 3-(2,4-dihydroxyphenyl)acrylate
• 英文别名: Ethyl (2e)-3-(2,4-dihydroxyphenyl)prop-2-enoate；ethyl (E)-3-(2,4-dihydroxyphenyl)prop-2-enoate
• CAS: 149542-04-1
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: MCVGZLLRIJTTTE-GQCTYLIASA-N

物化性质

• 熔点：
  193-195 °C
• 沸点：
  390.1±11.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(2,4-二羟基苯基)丙烯酸乙酯 在 吡啶 、 四(三苯基膦)钯 、 苯硅烷 、 potassium carbonate 、 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 11.0h， 生成 (E)-2-((E)-1-(2-isonicotinoylhydrazono)ethyl)phenyl 3-(2,4-dihydroxyphenyl)acrylate
  参考文献：
  名称：

  A multifunctional, light-activated prochelator inhibits UVA-induced oxidative stress

  摘要：

  UVA radiation can damage cells and tissues by direct photodamage of biomolecules as well as by initiating metal-catalyzed oxidative stress. In order to alleviate both concerns simultaneously, we synthesized a multifunctional prochelator PC-HAPI (2-((E)-1-(2-isonicotinoylhydrazono) ethyl)phenyl(trans)-3-(2,4-dihydroxyphenyl)acrylate) that contains a trans-(o-hydroxy)cinnamate ester photocleavable protecting group that is cleaved upon UVA exposure to release a coumarin, umbelliferone, and an aroylhydrazone metal chelator, HAPI (N'-[1-(2-hydroxyphenyl)ethyliden]isonicotinoylhydrazide). While the prochelator PC-HAPI exhibits negligible affinity for iron, it responds rapidly to UVA irradiation and converts to an iron-binding chelator that inhibits iron-catalyzed formation of reactive oxygen species and protects cells from UVA damage. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.048
• 作为产物：
  描述：

  (Z)-3-(2,4-dihydroxyphenyl)acrylic acid ethyl ester 在 Tris buffer 作用下， 以 乙腈 为溶剂， 生成 (E)-3-(2,4-二羟基苯基)丙烯酸乙酯
  参考文献：
  名称：

  带有荧光报告的双光子解笼锁：theo-Hydroxycinnamic 平台的评估

  摘要：

  本文评估了 o-羟基肉桂酸平台，用于设计具有单光子和双光子激发荧光报告的高效笼罩基团。通过偶联商业或现成的合成子，模型肉桂酸酯很容易一步制备。它们表现出大的单光子吸收，可以在近紫外范围内进行调整。通过 1 H NMR、UV-vis 吸收和稳态荧光发射研究单光子激发后的解笼锁。在整个研究系列中，笼底物在光解时定量释放。同时，uncaging 会释放强荧光副产物，可用作定量底物递送的报告基因。单光子吸收后导致解笼锁的双键光异构化的量子产率大多在 10% 范围内。利用解笼锁副产物有利的光物理特性，我们使用一系列基于荧光发射的技术来测量本肉桂酸酯的双光子激发的解笼锁横截面。在 750 nm 处显示 1-10 GM 范围内的值，它们与迄今为止报道的最有效的笼养组相比令人满意。值得注意的是，正如在活斑马鱼胚胎中观察到的结果所暗示的那样，双光子激发的解笼锁行为在体内得以保留。从目前收集到的数据的分析中提

  DOI：

  10.1021/ja0722022

文献信息

• Synthesis of Coumarins and Neoflavones through Zinc Chloride Catalyzed Hydroarylation of Acetylenic Esters with Phenols
  作者：Paulo Costa、Raquel Leão、Paula de F. de Moraes、Marcella Pedro

  DOI：10.1055/s-0031-1289576

  日期：2011.11

  Acetylenic esters react with oxygenated phenols under solvent-free conditions in the presence of only 5 mol% of zinc chloride as a catalyst to give coumarins and neoflavones in reasonable-to-good yields. phenols - catalysis - arylations - heterocycles - alkynes - esters

  乙炔酸酯在无溶剂条件下，在仅5 mol％的氯化锌作为催化剂的情况下，与含氧酚反应，以合理至良好的收率得到香豆素和新黄酮。 酚-催化-芳基化-杂环-炔烃-酯
• 3-Trifluoromethylated Coumarins and Carbostyrils by Radical Trifluoromethylation of<i>ortho</i>-Functionalized Cinnamic Esters
  作者：Slim Chaabouni、Florent Simonet、Alison François、Souhir Abid、Chantal Galaup、Stefan Chassaing

  DOI：10.1002/ejoc.201601181

  日期：2017.1.10

  regioselective synthesis of 3-trifluoromethylated coumarins. The reaction was performed by using the Togni reagent as the CF3 source under mild conditions and showed good functional- group tolerance. The scope of this copper-mediated method was further expanded to the synthesis of 3-trifluoromethylated carbostyrils starting from ortho-aminocinnamic derivatives. Interestingly, a sequential one-pot synthesis of

  开发了一种邻羟基肉桂酸酯的三氟甲基化方法，以实现 3-三氟甲基化香豆素的区域选择性合成。该反应采用 Togni 试剂作为 CF3 源，在温和条件下进行，显示出良好的官能团耐受性。这种铜介导的方法的范围进一步扩展到从邻氨基肉桂衍生物开始合成 3-三氟甲基化喹诺酮。有趣的是，进一步开发了从水杨醛开始的 3-三氟甲基化香豆素的连续一锅合成。探索了这种级联反应的机制，发现自由基途径与所得结果一致。
• Photoconversion of o-hydroxycinnamates to coumarins and its application to fluorescence imaging
  作者：Sung-Youl Cho、Young-Kyu Song、Joong-Gon Kim、Se-Young Oh、Chan-Moon Chung

  DOI：10.1016/j.tetlet.2009.06.031

  日期：2009.8

  (E)-o-Hydroxycinnamates were synthesized and their photochemical behavior was investigated in liquid and solid states. It was confirmed by H-1 NMR spectroscopy that the (E)-o-hydroxycinnamates converted into the corresponding coumarins via (Z)-o-hydroxycinnamate intermediates. The photoconversion was greatly accelerated in the presence of p-toluenesulfonic acid. The optical properties of the cinnamates were compared with those of the corresponding coumarins. Fluorescence imaging was successfully accomplished by photoirradiation of PMMA films containing the cinnamates. (C) 2009 Elsevier Ltd. All rights reserved.

  （E）-o-水煤气产物通过合成并研究了它们的光化学行为在液态和固态中。通过¹H核磁共振光谱分析法（H-1 NMR spectroscopy）确认，（E）-o-水煤气产物通过（Z）-o-水煤气中间体转化为相应的对调quaresin。在p-toluenesulfonic acid的存在下，光转变被大大加速。比较了与对应对调quaresin的光学性质。通过光照射聚甲基丙烯酸甲酯薄膜中的甲酰苯，成功实现了荧光成像。 （C）2009 Elsevier Ltd. All rights reserved.
• Amide compounds their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0339927A2

  公开（公告）日：1989-11-02

  New amide compounds of the general formula [I]: wherein R is a hydrogen atom or an acyl group, m is an integer of 1 to 3, n is an integer of 1 to 4, p is an integer of 1 or 2, q is an integer of 1 to 6, x is an integer of 2 to 6 and y is an integer of 1 to 3, with the proviso that, when (ii) n is 1, (iii) p is 1, (iv) q is 5 and (v) R is hydrogen atom, [(CH2)x-NH]y is neither (CH2)2NH(CH2)sNH-(CH2)3NH nor (CH2)2NH-(CH2)4NH(CH2)3NH, and salts thereof have excellent glutamate receptor-inhibiting activities, and they can be produced by the following reaction scheme: or wherein the symbols are as defined above except that the hydroxyl, imino or/and amino group or groups may be protected.

  通式[I]的新酰胺化合物： 其中 R 是氢原子或酰基，m 是 1 至 3 的整数，n 是 1 至 4 的整数，p 是 1 或 2 的整数，q 是 1 至 6 的整数，x 是 2 至 6 的整数，y 是 1 至 3 的整数，但条件是，当 (ii)n为1，(iii)p为1，(iv)q为5，(v)R为氢原子时，[(CH2)x-NH]y既不是(CH2)2NH(CH2)sNH-(CH2)3NH，也不是(CH2)2NH-(CH2)4NH(CH2)3NH： 或 其中符号如上定义，但羟基、亚氨基或/和氨基可被保护。
• Rh-Catalyzed Deformylative Coupling of Salicylaldehydes with Acrylates and Acrylamides
  作者：Maddali L. N. Rao、Boddu S. Ramakrishna

  DOI：10.1021/acs.joc.9b00602

  日期：2019.5.3

  An unprecedented deformylative coupling of salicylaldehydes to acrylates and acrylamides under Rh-catalyzed conditions is reported. These deformylative couplings afforded o-hydroxycinnamates and o-hydroxycinnamamides with broad functional group tolerance and high chemoselectivity under milder reaction conditions.