(R)-2-(benzo[b]thiophen-3-yl)-2-hydroxyacetic acid | 1370038-60-0

• 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: (R)-2-(benzo[b]thiophen-3-yl)-2-hydroxyacetic acid
• 英文别名: (2R)-2-(1-benzothiophen-3-yl)-2-hydroxyacetic acid
• CAS: 1370038-60-0
• 化学式: C₁₀H₈O₃S
• 分子量: 208.238
• InChiKey: PYTOKOXFWKLBDN-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  85.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-(benzo[b]thiophen-3-yl)-2-hydroxyacetic acid 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-1-(benzo[d]thiophen-3-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-(benzo[b]thiophen-3-yl)acetate 在 Rhizopus oryzae esterase F 、 水 作用下， 以 异丙醚 为溶剂， 反应 12.0h， 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

文献信息

• 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.