(R)-α-(benzofuran-2-yl)-α-hydroxyacetic acid | 1370038-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (R)-α-(benzofuran-2-yl)-α-hydroxyacetic acid
• 英文别名: (R)-2-(benzofuran-2-yl)-2-hydroxyacetic acid；(2R)-2-(1-benzofuran-2-yl)-2-hydroxyacetic acid
• CAS: 1370038-54-2
• 化学式: C₁₀H₈O₄
• 分子量: 192.171
• InChiKey: STTPAMXAKVGQLD-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-α-(benzofuran-2-yl)-α-hydroxyacetic acid 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-1-(benzofuran-2-yl)ethane-1,2-diol
  参考文献：
  名称：

  Synthesis of enantiomerically enriched (R)- and (S)-benzofuranyl- and benzo[b]thiophenyl-1,2-ethanediols via enantiopure cyanohydrins as intermediates

  摘要：

  The chemoenzymatic synthesis of highly enantiopure (R)- and (S)-benzofuranyl- and benzo[b]thio-phenyl-cyanohydrins and their chemical transformation into the corresponding heteroaryl-1,2-ethanediols is described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.018
• 作为产物：
  描述：

  ethyl (R)-2-acetoxy-2-(benzofuran-2-yl)acetate 在 Pseudomonas cepacia lipase 、 Rhizopus oryzae esterase F 、 水 作用下， 以 异丙醚 为溶剂， 反应 22.0h， 生成 (R)-α-(benzofuran-2-yl)-α-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

文献信息

• Enzymatic Enantioselective Decarboxylative Protonation of Heteroaryl Malonates
  作者：Ross Lewin、Mark Goodall、Mark L. Thompson、James Leigh、Michael Breuer、Kai Baldenius、Jason Micklefield

  DOI：10.1002/chem.201406014

  日期：2015.4.20

  α‐hydroxycarboxylic acids, including pharmaceutical precursors, from readily accessible α‐hydroxymalonates. The enzymatic method described here represents an improvement upon existing synthetic chemistry methods that have been used to produce similar compounds. The relationship between the structural features of these new substrates and the kinetics associated with their enzymatic decarboxylation is explored

  芳基/烯基丙二酸酯脱羧酶（AMDase）催化一系列双取代丙二酸的对映选择性脱羧质子化（EDP），以提供作为有价值的合成中间体的高手性羧酸。与迄今为止开发的非酶促EDP方法相比，AMDase具有许多优势，包括更高的对映选择性和更环境友好的反应条件。在本报告中，AMDase及其工程变体已用于从易于获得的α-羟基丙二酸酯生产一系列对映体富集的杂芳族α-羟基羧酸，包括药物前体。本文所述的酶促方法代表了已用于生产相似化合物的现有合成化学方法的改进。
• 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.
• Synthesis of enantiomerically enriched (R)- and (S)-benzofuranyl- and benzo[b]thiophenyl-1,2-ethanediols via enantiopure cyanohydrins as intermediates
  作者：László Csaba Bencze、Csaba Paizs、Monica Ioana Toşa、Elemér Vass、Florin Dan Irimie

  DOI：10.1016/j.tetasy.2010.01.018

  日期：2010.3

  The chemoenzymatic synthesis of highly enantiopure (R)- and (S)-benzofuranyl- and benzo[b]thio-phenyl-cyanohydrins and their chemical transformation into the corresponding heteroaryl-1,2-ethanediols is described. (C) 2010 Elsevier Ltd. All rights reserved.