(R)-1-(4-ethoxyphenyl)ethyl acetate | 1352328-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-(4-ethoxyphenyl)ethyl acetate
• 英文别名: 1-(4-ethoxyphenyl)ethyl acetate；[(1R)-1-(4-ethoxyphenyl)ethyl] acetate
• CAS: 1352328-31-4
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: MLVJFXUUKIMHNC-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-(4-ethoxyphenyl)ethyl acetate 在 immobilized CALB lipase 、 氨 作用下， 以 异丙醚 为溶剂， 反应 12.0h， 生成 (R)-4-乙氧基-α-甲基苯乙醇
  参考文献：
  名称：

  A tandem and fully enzymatic procedure for the green resolution of chiral alcohols: acylation and deacylation in non-aqueous media

  摘要：

  A green and fully enzymatic procedure for the resolution of chiral alcohols through lipase/esterase-catalyzed acylation and subsequent lipase-catalyzed aminolysis using anhydrous ammonia was demonstrated. Both enantiomers can be obtained in high ee values (up to >99%) under ambient reaction conditions. The solvent and acyl donors can be recycled, and the enzyme can be reused for up to five times. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.05.022
• 作为产物：
  描述：

  1-(4-乙氧基苯基)乙醇 在 仲丁醇 作用下， 以 异丙醚 为溶剂， 反应 24.0h， 以19.5%的产率得到(R)-4-乙氧基-α-甲基苯乙醇
  参考文献：
  名称：

  在非水介质中通过醇解对某些乙酸苄酯衍生物进行 CAL-B 催化的对映选择性脱乙酰化

  摘要：

  摘要 描述了在温和条件下通过来自南极念珠菌 (CAL-B) 的脂肪酶 B 催化的醇解对一组苄基乙酸酯进行对映选择性脱乙酰化。系统研究可以确定合适的亲核试剂/有机溶剂组合，并解释这些参数对酶催化反应的影响。在所有情况下，在转化率 36 % < C < 48 %、选择性达到 E > 500 时，获得的 (R)-醇具有高 ee（高达 >99%）。酶促反应性受溶剂疏水性和亲核试剂的结构/性质。此外，CAL-B 允许在非水介质中的酯交换之间进行对映互补：醇解和乙酰化。图形摘要

  DOI：

  10.1007/s10562-014-1470-7

文献信息

• Escherichia coli BioH: a highly enantioselective and organic solvent tolerant esterase for kinetic resolution of sec-alcohols
  作者：Bo Wang、Xiaoling Tang、Ji Liu、Hongwei Yu

  DOI：10.1016/j.tetlet.2010.09.135

  日期：2010.12

  Escherichia coli BioH, which is obligatory for biotin synthesis, was found to be an organic solvent tolerant esterase with high enantioselectivity for the kinetic resolution of sec-alcohols using free enzyme powder. With this esterase, a variety of racemic sec-alcohols were efficiently resolved with ee values of up to 99%. (C) 2010 Elsevier Ltd. All rights reserved.
• Racemization of secondary alcohols catalyzed by ruthenium: application to chemoenzymatic dynamic resolution
  作者：Mounia Merabet-Khelassi、Nicolas Vriamont、Louisa Aribi-Zouioueche、Olivier Riant

  DOI：10.1016/j.tetasy.2011.10.007

  日期：2011.10

  In this paper, we have shown that the [RuCl2(p-cymene)](2) complex associated with simple hemisalen ligands is able to racemize (S)-1-phenylethanol. The influence on the racemization process of the ligand's structure as well as the nature of a co-catalyst have been evaluated and optimized. This [RuCl2(p-cymene)](2)/Ligand/TEMPO racemization system was then associated with the Candida Antarctica B lipase in order to carry out dynamic kinetic resolution experiments on rac-phenylethanol. This led us to identify the best conditions for effective DKR, which was then applied to various secondary benzylic and aliphatic alcohols. It was thus possible to obtain (R)-1-cyclohexylethyl acetate from rac-1-cyclohexylethanol in quantitative conversion and with high enantioselectivity (98%). (C) 2011 Elsevier Ltd. All rights reserved.