ethyl 3-hydroxy-3-(thiophen-3-yl)propanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl 3-hydroxy-3-(thiophen-3-yl)propanoate
• 英文别名: ethyl 3-hydroxy-3-(3-thienyl)-propanoate；3-hydroxy-3-[3]thienyl-propionic acid ethyl ester；3-Hydroxy-3-[3]thienyl-propionsaeure-aethylester；Ethyl 3-hydroxy-3-(3-thienyl)propanoate；ethyl 3-hydroxy-3-thiophen-3-ylpropanoate
• 化学式: C₉H₁₂O₃S
• 分子量: 200.258
• InChiKey: FHRGPSQBWFCLEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  74.8
• 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-(thiophen-3-yl)propanoate 在 吡啶 、 4-二甲氨基吡啶 、 Candida rugose type VII lipase 、 水 作用下， 以 二氯甲烷 、 异丙醚 为溶剂， 生成 (R)-ethyl 3-hydroxy-3-(thiophen-3-yl)propanoate
  参考文献：
  名称：

  脂肪酶介导的使用脂肪酸衍生物的芳香族β-羟基酯的顺序拆分

  摘要：

  研究了在有机介质中脂肪酶催化的一系列芳香族β-羟基酯的动力学拆分。癸酸及其酯已成功地用作酰基供体，用于选择性的O-酰化。还研究了二酯的癸酸酯部分的区域和对映选择性酶促水解。研究了水，反应温度和溶剂类型的影响，以及底物结构对潜在的商用脂肪酶催化行为的影响。为了有效和高度立体选择性地合成新的和已知的目标化合物的两种对映异构体，开发了一种新的方法。

  DOI：

  10.1016/j.tetasy.2011.09.005
• 作为产物：
  描述：

  3-噻吩甲醛 、 碘代醋酸乙酯 在 air 、 Dimethylzinc 、 三苯基氧化膦 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 0.5h， 以92%的产率得到ethyl 3-hydroxy-3-(thiophen-3-yl)propanoate
  参考文献：
  名称：

  二甲基锌介导的碘乙酸乙酯与醛和酮的氧化促进的Reformatsky反应

  摘要：

  描述了一种由氧化剂促进并由二甲基锌介导的实用且通用的Reformatsky反应。该反应快速，可在温和的反应条件下于0°C与醛和酮一起运行。对映体选择性形式获得的初步结果表明，廉价的手性氨基醇可用于富挑战性地形成对映体富集的季立体异构中心。

  DOI：

  10.1002/adsc.200700572

文献信息

• Process for preparing 3-heteroaryl-3-hydroxypropanoic acid derivatives
  申请人：Berendes Frank

  公开号：US20060264641A1

  公开（公告）日：2006-11-23

  The invention relates to a process for preparing enantiomer-enriched 3-heteroaryl-3-hydroxypropanoic acid derivatives and 3-heteroaryl-1-aminopropan-3-ols, and to their use.

  本发明涉及一种制备对映富集的3-杂环基-3-羟基丙酸衍生物和3-杂环基-1-氨基丙醇的方法，以及它们的应用。
• A rapid and diverse construction of 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through double Reformatsky reaction
  作者：Masahiro Mineno、Yasuhiro Sawai、Kazuaki Kanno、Naotaka Sawada、Hideya Mizufune

  DOI：10.1016/j.tet.2013.10.079

  日期：2013.12

  A rapid and diverse synthesis of biologically important 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through a double Reformatsky reaction of aldehydes to delta-hydroxy-beta-ketoesters followed by lactonization is described. Due to the high functional group tolerance and reaction site discrimination between aldehyde, nitrile, and ester groups in the substrate, the protocol can provide the dihydropyrones with bromo, nitro, carboxylic acid, and beta-ketoester groups, which are suitable for the further derivatizations. Furthermore, the protocol has been successfully applied to the rapid total synthesis of naturally occurring Yangonin. (C) 2013 Elsevier Ltd. All rights reserved.
• Lipases A and B from Candida antarctica in the enantioselective acylation of ethyl 3-heteroaryl-3-hydroxypropanoates: aspects on the preparation and enantiopreference
  作者：Jürgen Brem、Arto Liljeblad、Csaba Paizs、Monica Ioana Toşa、Florin-Dan Irimie、Liisa T. Kanerva

  DOI：10.1016/j.tetasy.2011.01.027

  日期：2011.2

  The preparative scale kinetic resolution of racemic ethyl 2- and 3-furyl- and 2- and 3-thienyl-3-hydroxypropanoates has been performed by Candida antarctica lipases A and B with vinyl esters. A study based on the present work together with the literature has been carried out in terms of lipase enantiopreference and substrate structure. We also discuss the excellent behavior of the lipase A in O-acylations of secondary alcohols with respect to enantiopreference. (C) 2011 Elsevier Ltd. All rights reserved.
• Carbonyl Derivatives of Thiophene. I. The Reformatsky Reaction with α-Bromoesters
  作者：Robert D. Schuetz、Wm. H. Houff

  DOI：10.1021/ja01612a036

  日期：1955.4
• Pradefovir: A Prodrug That Targets Adefovir to the Liver for the Treatment of Hepatitis B
  作者：K. Raja Reddy、Michael C. Matelich、Bheemarao G. Ugarkar、Jorge E. Gómez-Galeno、Jay DaRe、Kristin Ollis、Zhili Sun、William Craigo、Timothy J. Colby、James M. Fujitaki、Serge H. Boyer、Paul D. van Poelje、Mark D. Erion

  DOI：10.1021/jm7012216

  日期：2008.2.1

  Adefovir dipivoxil, a marketed drug for the treatment of hepatitis B, is dosed at submaximally efficacious doses because of renal toxicity. In an effort to improve the therapeutic index of adefovir, 1-aryl-1,3-propanyl prodrugs were synthesized with the rationale that this selectively liver-activated prodrug class would enhance liver levels of the active metabolite adefovir diphosphate (ADV-DP) and/or decrease kidney exposure. The lead prodrug (14, MB06866, pradefovir), identified from a variety of in vitro and in vivo assays, exhibited good oral bioavailability (F = 42%, mesylate salt, rat) and rate of prodrug conversion to ADV-DP. Tissue distribution studies in the rat using radiolabeled materials showed that cyclic 1-aryl-1,3-propanyl prodrugs enhance the delivery of adefovir and its metabolites to the liver, with pradefovir exhibiting a 12-fold improvement in the liver/kidney ratio over adefovir dipivoxil.