ethyl 2-(benzo[b]thiophen-3-yl)-2-hydroxyacetate

• 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: ethyl 2-(benzo[b]thiophen-3-yl)-2-hydroxyacetate
• 英文别名: Ethyl 2-(1-benzothiophen-3-yl)-2-hydroxyacetate
• 化学式: C₁₂H₁₂O₃S
• 分子量: 236.291
• InChiKey: DLPULMZKVNDHGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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 2-(benzo[b]thiophen-3-yl)-2-hydroxyacetate 在 Rhizopus oryzae esterase F 、 水 作用下， 以 异丙醚 为溶剂， 反应 14.0h， 生成 (R)-2-(benzo[b]thiophen-3-yl)-2-hydroxyacetic acid
  参考文献：
  名称：

  Sequential enzymatic procedure for the preparation of enantiomerically pure 2-heteroaryl-2-hydroxyacetic acids

  摘要：

  Starting from the racemic 2-benzofuranyl- and 2-benzo[b]thiophenyl-2-hydroxyacetic acid ethyl esters as substrates, a general method was developed for the efficient synthesis of the corresponding highly enantiomerically enriched (ee up to 99%) (R)- and (S)-2-heteroaryl-2-hydroxyacetic acids. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.019
• 作为产物：
  描述：

  2-(benzo[b]thiophen-3-yl)-2-hydroxyacetonitrile 在 盐酸 、 氯化亚砜 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 28.5h， 生成 ethyl 2-(benzo[b]thiophen-3-yl)-2-hydroxyacetate
  参考文献：
  名称：

  Sequential enzymatic procedure for the preparation of enantiomerically pure 2-heteroaryl-2-hydroxyacetic acids

  摘要：

  Starting from the racemic 2-benzofuranyl- and 2-benzo[b]thiophenyl-2-hydroxyacetic acid ethyl esters as substrates, a general method was developed for the efficient synthesis of the corresponding highly enantiomerically enriched (ee up to 99%) (R)- and (S)-2-heteroaryl-2-hydroxyacetic acids. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.019

文献信息

• Ytterbium(III) Trifluoromethanesulfonate Catalyzed Electrophilic Aromatic Substitution with Glyoxalate and Lipase-Mediated Product Resolution:  A Convenient Route to Optically Active Aromatic α-Hydroxy Esters
  作者：Wei Zhang、Peng George Wang

  DOI：10.1021/jo991916v

  日期：2000.7.1
• US7767811B2
  申请人：——

  公开号：US7767811B2

  公开（公告）日：2010-08-03
• [EN] HALLUCINOGENIC AND NON-HALLUCINOGENIC SEROTONIN RECEPTOR AGONISTS AND METHODS OF MAKING AND USING THE SAME<br/>[FR] AGONISTES HALLUCINOGÈNES ET NON HALLUCINOGÈNES DU RÉCEPTEUR DE LA SÉROTONINE ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：[en]PSILOSTERICS, LLC

  公开号：WO2023018864A1

  公开（公告）日：2023-02-16

  Hallucinogenic and non-hallucinogenic serotonin receptor agonists are disclosed herein in addition to methods of making and using the same.
• Sequential enzymatic procedure for the preparation of enantiomerically pure 2-heteroaryl-2-hydroxyacetic acids
  作者：Mara Ana Naghi、László Csaba Bencze、Jürgen Brem、Csaba Paizs、Florin Dan Irimie、Monica Ioana Toşa

  DOI：10.1016/j.tetasy.2012.01.019

  日期：2012.1

  Starting from the racemic 2-benzofuranyl- and 2-benzo[b]thiophenyl-2-hydroxyacetic acid ethyl esters as substrates, a general method was developed for the efficient synthesis of the corresponding highly enantiomerically enriched (ee up to 99%) (R)- and (S)-2-heteroaryl-2-hydroxyacetic acids. (C) 2012 Elsevier Ltd. All rights reserved.