ethyl 3-hydroxy-3-(3-methoxyphenyl)propanoate | 51699-39-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 3-hydroxy-3-(3-methoxyphenyl)propanoate
• CAS: 51699-39-9
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: XWYOLMUIQADPAE-UHFFFAOYSA-N

物化性质

• 沸点：
  354.7±32.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-hydroxy-3-(3-methoxyphenyl)propanoate 在 氢氧化钾 、 正丁基锂 、 三氯化铝 、 氯化亚砜 、 四丁基氟化铵 、 仲丁基锂 、 sodium hydride 、 三乙胺 、 N,N-二甲基甲酰胺 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 143.0h， 生成 5,7,8-triphenyl-2-naphtol
  参考文献：
  名称：

  Photochemistry of some extended .pi.-systems: type A and aryl rearrangements of systems with extended conjugation related to cyclohexadienones and cyclohexenones. Mechanistic and exploratory organic photochemistry

  摘要：

  DOI：

  10.1021/jo00285a028
• 作为产物：
  描述：

  3-甲氧基苯乙酮 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 甲苯 、 mineral oil 为溶剂， 反应 17.0h， 生成 ethyl 3-hydroxy-3-(3-methoxyphenyl)propanoate
  参考文献：
  名称：

  Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: the influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications

  摘要：

  Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.06.004

文献信息

• N-Heterocyclic carbene mediated Reformatsky reaction of aldehydes with α-trimethylsilylcarbonyl compounds
  作者：Xiao-Lei Zou、Guang-Fen Du、Wan-Fu Sun、Lin He、Xiao-Wei Ma、Cheng-Zhi Gu、Bin Dai

  DOI：10.1016/j.tet.2012.11.015

  日期：2013.1

  N-Heterocyclic carbenes have been employed as highly efficient organocatalysts to mediate silyl-Reformatsky type reaction. In the presence of only 0.5 mol % nucleophilic carbene 1, various aldehydes coupled with α-trimethylsilylethylacetate very smoothly in DMF at room temperature to provide the corresponding β-hydroxyesters in moderate to high yields. α-Trimethylsilylketone and α-trimethylsilylamide

  N-杂环卡宾已被用作高效的有机催化剂，以介导甲硅烷基-Reformatsky型反应。在仅0.5mol％亲核卡宾1的存在下，各种醛与α-三甲基甲硅烷基乙基乙酸乙酯在室温下在DMF中非常平滑地偶联，以中等至高产率提供相应的β-羟基酯。α-三甲基甲硅烷基酮和α-三甲基甲硅烷基酰胺也可以进行加成反应，以中等收率得到β-羟基酮和β-羟基酰胺。
• Synthesis, molecular docking and kinetic properties of β-hydroxy-β-phenylpropionyl-hydroxamic acids as Helicobacter pylori urease inhibitors
  作者：Zhu-Ping Xiao、Zhi-Yun Peng、Jing-Jun Dong、Rui-Cheng Deng、Xu-Dong Wang、Hui Ouyang、Pan Yang、Juan He、Yuan-Feng Wang、Man Zhu、Xiao-Chun Peng、Wan-Xi Peng、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2013.07.047

  日期：2013.10

  Inhibition of urease results in Helicobacter pylori growth arrest in the stomach, promoting urease as promising targets for gastrointestinal ulcer therapy. Twenty hybrid derivatives of flavonoid scaffold and hydroxamic acid, β-hydroxy-β-phenylpropionylhydroxamic acids, were therefore synthesized and evaluated against H. pylori urease. Biological evaluation of these compounds showed improved urease

  尿素酶的抑制导致幽门螺杆菌在胃中的生长停滞，从而促进尿素酶成为胃肠道溃疡治疗的有希望的靶标。因此，合成了黄酮类支架和异羟肟酸的二十种杂合衍生物，β-羟基-β-苯基丙酰基异羟肟酸，并针对幽门螺杆菌脲酶进行了评估。这些化合物的生物学评估表明，尿素酶抑制作用得到改善，表现出微摩尔至中纳摩尔级的IC 50值。最重要的是，3-（3-氯苯基）-3-羟基丙酰基-异羟肟酸（6g）表现出高效能，IC 50为0.083±0.004μM，K i为0.014±0.003μM，表明6g是开发新型抗溃疡药的优秀候选者。为了首次了解晶体学和动力学研究之间的矛盾，提出了一种竞争机制和非竞争机制的混合物，这是我们的分子对接研究所支持的。
• A Simple and Efficient Procedure of Low Valent Iron- or Copper-Mediated Reformatsky Reaction of Aldehydes
  作者：Angshuman Chattopadhyay、Akhil Kr. Dubey

  DOI：10.1021/jo0710984

  日期：2007.11.1

  An operationally simple and very efficient procedure of Reformatsky reaction of aldehydes has been carried out in THF in the presence of low valent iron or copper which were prepared in situ employing a bimetal redox strategy through reduction of FeCl3 or CuCl2−2H2O with magnesium.

  在低价铁或铜的存在下，已在四氢呋喃中进行了操作简单且非常有效的醛重整反应程序，该过程使用双金属氧化还原策略通过将FeCl 3或CuCl 2 -2H 2 O还原为低价铁或铜而现场制得。镁。
• Bu4N+-Controlled Addition and Olefination with Ethyl 2-(Trimethylsilyl)acetate via Silicon Activation
  作者：Donal O’Shea、Manas Das、Atul Manvar、Ian Fox、Dilwyn Roberts

  DOI：10.1055/s-0036-1588805

  日期：2017.11

  β-hydroxy esters, whereas employing catalytic Bu4NOTMS gave α,β-unsaturated esters. The established reaction conditions were applicable to a diverse range of aromatic, heteroaromatic, aliphatic aldehydes and ketones. Reactions were achieved at room temperature without taking any of the specialized precautions that are in place for other organometallics. A stepwise olefination pathway via silylated

  催化 Bu4NOAc 作为 2-（三甲基甲硅烷基）乙酸乙酯的硅活化剂，在 THF 中，用于合成 β-羟基酯，而使用催化 Bu4NOTMS 产生 α,β-不饱和酯。既定的反应条件适用于各种芳香族、杂芳香族、脂肪族醛和酮。反应是在室温下完成的，没有采取任何其他有机金属的专门预防措施。已经证明了通过甲硅烷基化 β-羟基酯随后消除形成 α,β-不饱和酯的逐步烯化途径。选择性产物形成的关键在于使用较弱的乙酸盐活化剂，它抑制随后的消除，而较强的 TMSO– 活化剂（和碱）促进添加和消除步骤。
• A Facile One-Pot Synthesis of Chiral β-Amino Esters
  作者：Tanasri Bunlaksananusorn、Florian Rampf

  DOI：10.1055/s-2005-917108

  日期：——

  We report a facile one-pot synthesis of chiral β-amino ­esters via direct reductive amination of β-keto esters with ­ammonium acetate (NH4OAc) and H2 in the presence of chiral Ru-ClMeOBIPHEP catalysts using 2,2,2-trifluoroethanol (TFE) as a solvent, leading to β-amino esters in high yields with high ­enantioselectivities (up to 99% ee).

  我们报道了一种简便的一锅法合成手性β-氨基酯的方法，利用β-酮酯与醋酸铵（NH4OAc）和氢气的直接还原胺化反应，采用手性Ru-ClMeOBIPHEP催化剂，溶剂为2,2,2-三氟乙醇（TFE），最终得到高产率且高对映体选择性（高达99% ee）的β-氨基酯。