methyl-2-hydroxy-3-phenylacrylate | 80540-55-2

• 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: methyl-2-hydroxy-3-phenylacrylate
• 英文别名: Methyl 2-hydroxy-3-phenylprop-2-enoate
• CAS: 80540-55-2
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: KIHSYCSFCHJUQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：

  methyl-2-hydroxy-3-phenylacrylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以71%的产率得到甲基2-羟基-3-苯丙酸酯
  参考文献：
  名称：

  Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols

  摘要：

  alpha-hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic alpha-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00154-8
• 作为产物：
  描述：

  2-甲基-4-(苯基亚甲基)噁唑-5(4h)-酮 在 盐酸 、 乙酰氯 作用下， 生成 methyl-2-hydroxy-3-phenylacrylate
  参考文献：
  名称：

  Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols

  摘要：

  alpha-hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic alpha-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00154-8

文献信息

• 3-Hydroxy-1,5-dihydro-2H-pyrrol-2-ones as novel antibacterial scaffolds against methicillin-resistant Staphylococcus aureus
  作者：Alexander Q. Cusumano、Joshua G. Pierce

  DOI：10.1016/j.bmcl.2018.02.047

  日期：2018.9

  antibacterial agents against methicillin-resistant S. aureus (MRSA) and methicillin-resistant S. epidermidis (MRSE). Lead compound 38 showed minimum inhibitory concentrations (MICs) of 8 and 4 μg/mL against MRSA and MRSE, respectively. Furthermore, compound 38 displayed a MIC of 8–16 μg/mL against linezolid-resistant MRSA. These molecules, previously underexplored as antibacterial agents, serve as a

  在此，我们报告了3-羟基-1,5-二氢-2H-吡咯-2-酮作为抗甲氧西林耐药金黄色葡萄球菌（MRSA）和耐甲氧西林表皮葡萄球菌（MRSE）的抗菌剂的合成和评估。铅化合物38对MRSA和MRSE的最小抑菌浓度（MIC）分别为8和4μg/ mL。此外，化合物38对耐利奈唑胺的MRSA的MIC为8-16μg/ mL。这些以前未被开发为抗菌剂的分子，可作为抗菌素开发的新支架。
• Stereoselective, Multicomponent Approach to Quaternary Substituted Hydroindole Scaffolds
  作者：Nicholas P. Massaro、Joshua G. Pierce

  DOI：10.1021/acs.orglett.0c01650

  日期：2020.7.2

  Amaryllidaceae alkaloids have been a target of synthesis for decades due to their complex architectures and biological activity. A central feature of these natural product cores is a quaternary substituted hydroindole heterocycle. Building off the foundation of our previous multicomponent approach to highly functionalized pyrrolidinones, herein we report a highly convergent, diastereoselective, multicomponent

  数十年来，金莲花科生物碱一直是合成的目标，因为它们复杂的结构和生物活性。这些天然产物核心的主要特征是季取代的氢吲哚杂环。在我们先前对高度官能化的吡咯烷酮的多组分方法的基础之上，本文报道了一种高度收敛，非对映选择性的多组分方法，可用于获得存在于可丽宁，甘露糖胺，普他他汀和各种其他生物活性生物碱中的氢化吲哚核。这些支架还可用作药物样分子和天然产物（如文库生成）的构建基块。
• Direct Access to Highly Functionalized Heterocycles through the Condensation of Cyclic Imines and α-Oxoesters
  作者：Alexander Q. Cusumano、Matthew W. Boudreau、Joshua G. Pierce

  DOI：10.1021/acs.joc.7b02572

  日期：2017.12.15

  preparation of 2-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-3-ones and 2-hydroxy-6,7,8,8a-tetrahydroindolizin-3(5H)-ones from a condensation cyclization of α-oxoesters with five- and six-membered cyclic imines, respectively, is reported. This transformation enables a concise, three-step synthesis of the natural products phenopyrrozin and p-hydroxyphenopyrrozin. Further, biologically relevant scaffolds

  2-羟基-5,6,7,7a-四氢-3 H-吡咯烷酮-3-酮和2-羟基-6,7,8,8a-四氢吲哚-3（5 H）的克级制备方法。据报道，α-氧代酸酯分别与五元和六元环状亚胺的缩合环化反应得到的α-酮。该转化使得天然产物苯并吡嗪和对羟基苯并吡嗪的简明的三步合成成为可能。此外，生物相关的支架，如α-β季-HOMO脯氨酸和β内酰胺类，也在两准备从三步骤多功能-2-羟基-5,6,7,7a-四氢3 ħ -吡咯烷-3-一核。
• Molecular structure of methyl phenylpyruvates studied by 1H NMR and IR spectroscopies and quantum mechanical calculations
  作者：H.-H. Lee、T. Takai、H. Senda、A. Kuwae、K. Hanai

  DOI：10.1016/s0022-2860(98)00374-3

  日期：1998.8

  Abstract Molecular structure of methyl phenylpyruvate (MPP) and its p -substituted derivatives has been investigated by 1 H NMR and IR spectroscopies. The spectral data point out that MPPs take the enol form both in solution and in the solid state. The ab initio calculations were carried out in order to get information on the configurational and conformational preferences in the enol form. It is suggested

  摘要 通过 1 H NMR 和红外光谱研究了苯基丙酮酸甲酯 (MPP) 及其对位取代衍生物的分子结构。光谱数据指出 MPP 在溶液和固态中均采用烯醇形式。进行 ab initio 计算是为了获得有关烯醇形式的构型和构象偏好的信息。计算表明，烯醇OH基团和酯CO基团之间的分子间和分子内氢键对构象异构体的稳定很重要。
• Asymmetric transfer hydrogenation of α-azido acrylates
  作者：Yang Ji、Ping Xue、Dan-Dan Ma、Xue-Qiang Li、Peiming Gu、Rui Li

  DOI：10.1016/j.tetlet.2014.11.072

  日期：2015.1

  The asymmetric transfer hydrogenation of alpha-azido acrylates has been explored, a range of alpha-hydroxy esters are produced with good enantioselectivities (80-90% ee). The reaction was conducted in the wet HCO2H/NEt3 with Ru-TsDPEN A. (C) 2014 Elsevier Ltd. All rights reserved.