(S)-ethyl 3-(benzo[b]thiophen-3-yl)-3-hydroxypropanoate | 1159407-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (S)-ethyl 3-(benzo[b]thiophen-3-yl)-3-hydroxypropanoate
• 英文别名: ethyl (S)-3-(benzo[b]thiophen-3-yl)-3-hydroxypropanoate；ethyl (3S)-3-(1-benzothiophen-3-yl)-3-hydroxypropanoate
• CAS: 1159407-34-7
• 化学式: C₁₃H₁₄O₃S
• 分子量: 250.318
• InChiKey: SMXNFNYECBSEEN-NSHDSACASA-N

物化性质

• 沸点：
  415.6±30.0 °C(predicted)
• 密度：
  1.269±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (S)-ethyl 3-(benzo[b]thiophen-3-yl)-3-hydroxypropanoate 在 pig liver esterase 、 水 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 生成 (S)-3-(benzo[b]thiophen-3-yl)-3-hydroxypropanoic acid
  参考文献：
  名称：

  Enzyme-catalyzed synthesis of (R)- and (S)-3-heteroaryl-3-hydroxy-propanoic acids and their derivatives

  摘要：

  Starting from the racemic 3-benzofuranyl- and 3-benzo[b]thiophenyl-3-hydroxypropanoic acid ethyl esters as substrates, various multistep enzymatic procedures were developed for the efficient synthesis of the corresponding highly enantiomerically enriched (R)- and (S)-3-heteroaryl-3-hydroxypropanoic acids. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.001
• 作为产物：
  描述：

  (S)-2-(ethoxycarbonyl)-1-(benzo[b]thiophen-3-yl)ethyl butyrate 在 Burkholderia cepacia lipase 、 水 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 生成 (S)-ethyl 3-(benzo[b]thiophen-3-yl)-3-hydroxypropanoate
  参考文献：
  名称：

  Enzyme-catalyzed synthesis of (R)- and (S)-3-heteroaryl-3-hydroxy-propanoic acids and their derivatives

  摘要：

  Starting from the racemic 3-benzofuranyl- and 3-benzo[b]thiophenyl-3-hydroxypropanoic acid ethyl esters as substrates, various multistep enzymatic procedures were developed for the efficient synthesis of the corresponding highly enantiomerically enriched (R)- and (S)-3-heteroaryl-3-hydroxypropanoic acids. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.001

文献信息

• Lipase mediated sequential resolution of aromatic β-hydroxy esters using fatty acid derivatives
  作者：Jürgen Brem、Mara Naghi、Monica-Ioana Toşa、Zoltán Boros、László Poppe、Florin-Dan Irimie、Csaba Paizs

  DOI：10.1016/j.tetasy.2011.09.005

  日期：2011.9

  The lipase-catalyzed kinetic resolution of a series of aromatic β-hydroxy esters in organic media has been investigated. Decanoic acid and its esters were successfully used as acyl donors for selective O-acylation. The regio- and enantioselective enzymatic hydrolysis of the decanoate moiety of the diesters was also investigated. The effects of water, reaction temperature, and solvent type, and also

  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。