(S)-1-acetoxy-1-(benzo[d]thiazol-2-yl)ethane | 1059697-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (S)-1-acetoxy-1-(benzo[d]thiazol-2-yl)ethane
• 英文别名: [(1S)-1-(1,3-benzothiazol-2-yl)ethyl] acetate
• CAS: 1059697-95-8
• 化学式: C₁₁H₁₁NO₂S
• 分子量: 221.28
• InChiKey: LRSZTTWRBNFVPO-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-乙酰氧基-1-(苯并[d]噻唑-2-基)乙烷 在 Candida antarctica lipase B 、 乙醇 作用下， 反应 28.0h， 生成 (R)-1-(benzo[d]thiazol-2-yl)ethanol 、 (S)-1-acetoxy-1-(benzo[d]thiazol-2-yl)ethane
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of racemic 1-heteroarylethanols—experimental and QM/MM study

  摘要：

  The kinetic resolution of racemic 1-(benzothiazol-2-yl)ethanol rac-2a, 1-(benzo[b]thiophen-2-yl)ethanol rac-2b, 1 -(benzo[b]furan-3-yl)ethanol rac-2c and 1-(benzo[b]thiophen-3-yl)ethanol rac-2d was studied by enantiomer selective acylation catalyzed by a selection of commercially available and in house produced lipases. Alcoholysis of the Corresponding racemic acetates rac-3a-d catalyzed by Candida antarctica lipase B (CaLB) was also investigated. Two racemic 1-heteroarylethanols rac-2a,b were prepared by addition of the corresponding lithiated heteroarylic compounds la,b to acetaldehyde, whereas two others, rac-2c,d were synthesized by the addition of MeMgl onto the corresponding heteroaryl-carbaldehydes 1c,d. The high enantiomer selectivities of CaLB in the acylation of racemic 1-heteroarylethanols rac-2a-d allowed the determination of the enantiomeric preference of these enzymatic acetylation reactions by QM/MM [pm3/uff or hf(3-21+g**)/uff] calculations. For acetylation of each of the racemic alcohols rac-2a-d, four possible tetrahedral intermediate states were Compared and analyzed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.004

文献信息

• Chemoenzymatic synthesis of (R)- and (S)-1-heteroarylethanols
  作者：Monica Ioana Toşa、Paula Veronica Podea、Csaba Paizs、Florin Dan Irimie

  DOI：10.1016/j.tetasy.2008.08.023

  日期：2008.9

  A chemoenzymatic methodology for the synthesis of highly enantiomerically enriched (S)- and (R)-1-heteroarylethanols by enantioselective bioreduction with baker's yeast of the Corresponding 1-heteroarylethanones followed by three racemization free chemical steps including a Mitsunobu reaction was developed. (C) 2008 Elsevier Ltd. All rights reserved.