3-羟基-3-[2-甲氧基苯基]丙酸乙酯 | 70200-18-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-羟基-3-[2-甲氧基苯基]丙酸乙酯
• 英文名称: ethyl 3-hydroxy-3-(2-methoxyphenyl)propanoate
• CAS: 70200-18-9
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: GZSFVEPHHPZXTL-UHFFFAOYSA-N

物化性质

• 沸点：
  150-154 °C(Press: 10 Torr)
• 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：

  3-羟基-3-[2-甲氧基苯基]丙酸乙酯 在 immobilised Candida parapsilosis ATCC 7330 whole cells 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 以75%的产率得到(S)-ethyl 3-hydroxy-3-(2-methoxyphenyl)propanoate
  参考文献：
  名称：

  Deracemisation of β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330: substrate specificity and mechanistic investigation

  摘要：

  Deracemisation of aryl substituted beta-hydroxy esters by immobilised whole cells of Candida parapsilosis ATCC 7330 gave > 99% ee and up to 75% yield of their corresponding (S)-enantiomers. Mechanistic investigation of the deracemisation reaction carried out using a deuterated substrate, ethyl 3-deutero-3-hydroxy-3-phenyl propanoate revealed that while the (S)-enantiomer remains unreacted the (R)enantiomer undergoes enantioselective oxidation to its corresponding ketoester, which on complementary enantiospecific reduction gives the (S)-enantiomer in high yield and % ee. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.045
• 作为产物：
  描述：

  (2-甲氧基苯甲酰)乙酸乙酯 在 sodium tetrahydroborate 作用下， 生成 3-羟基-3-[2-甲氧基苯基]丙酸乙酯
  参考文献：
  名称：

  Deracemisation of β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330: substrate specificity and mechanistic investigation

  摘要：

  Deracemisation of aryl substituted beta-hydroxy esters by immobilised whole cells of Candida parapsilosis ATCC 7330 gave > 99% ee and up to 75% yield of their corresponding (S)-enantiomers. Mechanistic investigation of the deracemisation reaction carried out using a deuterated substrate, ethyl 3-deutero-3-hydroxy-3-phenyl propanoate revealed that while the (S)-enantiomer remains unreacted the (R)enantiomer undergoes enantioselective oxidation to its corresponding ketoester, which on complementary enantiospecific reduction gives the (S)-enantiomer in high yield and % ee. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.045

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。
• P(<i>i</i>-PrNCH₂CH₂)₃N: Efficient Catalyst for Synthesizing β-Hydroxyesters and α,β-Unsaturated Esters using α-Trimethylsilylethylacetate (TMSEA)
  作者：Kuldeep Wadhwa、John G. Verkade

  DOI：10.1021/jo900477q

  日期：2009.6.5

  We present an efficient synthesis of β-hydroxyesters and α,β-unsaturated esters via activation of the silicon−carbon bond of α-trimethylsilylethylacetate using catalytic amounts of the commercially available P(i-PrNCH2CH2)3N 1a. Selectivity for either of these two products can be achieved simply by altering the catalyst loading and reaction temperature to afford addition or stereoselective condensation

  我们提出了通过使用催化量的市售P（i- PrNCH 2 CH 2）3 N 1a活化α-三甲基甲硅烷基乙酸乙酯的硅碳键来有效合成β-羟基酯和α，β-不饱和酯的方法。通过改变催化剂的加入量和反应温度以提供加成或立体选择性缩合，可以简单地实现对这两种产物中任一种的选择性。这种方法比较温和，可以耐受各种各样的官能团。
• Rate Enhancement in CAN-Promoted Pd(PPh₃)₂Cl₂-Catalyzed Oxidative Cyclization: Synthesis of 2-Ketofuran-4-carboxylate Esters
  作者：Sureeporn Ruengsangtongkul、Nattawadee Chaisan、Charnsak Thongsornkleeb、Jumreang Tummatorn、Somsak Ruchirawat

  DOI：10.1021/acs.orglett.9b00053

  日期：2019.4.19

  Stoichiometric ceric ammonium nitrate (CAN) and a catalytic amount of Pd(PPh3)2Cl2 (5 mol %) can rapidly produce multisubstituted 2-ketofuran-4-carboxylate esters from 2-propargylic 1,3-ketoesters via oxidative O-cyclization reaction. Pd(PPh3)2Cl2 was found to be the crucial catalyst as its inclusion greatly enhanced the rate of the reaction and cleanly afforded the products within minutes. Over 30

  化学计量的硝酸铈铵（CAN）和Pd（PPH催化量3）2氯2（5摩尔％）可以迅速产生通过氧化多取代2- ketofuran -4-羧酸酯由2-丙炔-1,3-酮酯ø -环化反应。发现Pd（PPh 3）2 Cl 2是关键催化剂，因为它的加入大大提高了反应速度，并在数分钟内干净地得到了产物。超过30种底物已成功转化为所需化合物，且收率大多为中度到良好。
• A Practical Method for the Reformatsky Reaction of Aldehydes
  作者：Angshuman Chattopadhyay、Avinash Salaskar

  DOI：10.1055/s-2000-6378

  日期：——

  Reformatsky reaction of aliphatic aldehydes has been performed successfully by the addition of BF3 · OEt2 to a stirred suspension of aldehyde, bromo ester and Zn dust in aqueous THF. For aromatic aldehydes, addition of benzoyl peroxide is also required to effect the reaction.

  通过向在水性四氢呋喃中搅拌的醛、溴酯和锌粉悬浮液中加入BF3·OEt2，成功实现了脂肪族醛的Reformatsky反应。对于芳香族醛，还需要加入过氧化苯甲酰以促使反应进行。
• 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。