(S)-(-)-1-(4-乙氧基苯基)乙酸乙酯 | 1260074-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-(-)-1-(4-乙氧基苯基)乙酸乙酯
• 英文名称: (S)-(-)-1-(4-ethoxyphenyl)ethyl acetate
• 英文别名: 1-(4-ethoxyphenyl)ethyl acetate；[(1S)-1-(4-ethoxyphenyl)ethyl] acetate
• CAS: 1260074-16-5
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: MLVJFXUUKIMHNC-VIFPVBQESA-N

物化性质

• 沸点：
  279.6±23.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

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

• 作为产物：
  描述：

  咪唑并[2,1-b]喹唑啉-2(3H)-酮,1,5-二氢-7,8-二甲基- 在 偶氮二甲酸二异丙酯 、 sodium carbonate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 96.0h， 生成 (S)-(-)-1-(4-乙氧基苯基)乙酸乙酯
  参考文献：
  名称：

  A green route to enantioenriched (S)-arylalkyl carbinols by deracemization via combined lipase alkaline-hydrolysis/Mitsunobu esterification

  摘要：

  Herein we report results of the chemoenzymatic deracemization of a range of secondary benzylic acetates 1a-9a via a sequence of hydrolysis with CAL-B lipase in non-conventional media, combined with esterification of the recovered alcohol according to the Mitsunobu protocol following an enzymatic kinetic resolution (KR). The KR of racemic acetates 1a-9a via an enzymatic hydrolysis, with CAL-B lipase and Na2CO3, in non-aqueous media was optimized and gave high selectivities (E >> 200) at good conversions (C >49%) for all of the substrates studied. This method competes well with the traditional one performed in a phosphate buffer solution. The deracemization using Mitsunobu inversion gave the (S)-acetates in moderate to excellent enantiomeric excess 75% < ee < 99%, in acceptable isolated yields 70% < yield < 89%, and with some variations according to the acetate structure. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.01.020

文献信息

• CAL-B-Catalyzed Enantioselective Deacetylation of Some Benzylic Acetate Derivatives Via Alcoholysis in Non-aqueous Media
  作者：Amna Zaïdi、Mounia Merabet-Khelassi、Louisa Aribi-Zouioueche

  DOI：10.1007/s10562-014-1470-7

  日期：2015.4

  Abstract Enantioselective deacetylation of a set of benzylic acetates via alcoholysis catalyzed by Lipase B from Candida antarctica (CAL-B), under mild conditions is described. A systematic study allows to determine the appropriate combination nucleophile/organic solvent and also to explain the influence of these parameters on the enzymatic catalytic reaction. In all cases, (R)-alcohols are obtained

  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
• Green methodology for enzymatic hydrolysis of acetates in non-aqueous media via carbonate salts
  作者：Mounia Merabet-Khelassi、Zahia Houiene、Louisa Aribi-Zouioueche、Olivier Riant

  DOI：10.1016/j.tetasy.2012.06.001

  日期：2012.6

  Herein we report a new approach to enantiomerically enriched acetates using a lipase-catalyzed hydrolysis in non-aqueous media by alkaline carbonate salts. The use of sodium carbonate in the enzymatic hydrolysis with Candida antarctica lipase B (CAL-B) of racemic acetates shows a large enhancement of the reactivity and selectivity of this lipase. The role of the carbonate salts, the amount and the

  本文中，我们报告了一种新方法，可利用脂肪酶催化的非水介质中碱性碳酸盐在对映体上富集乙酸盐。在外消旋乙酸的南极假丝酵母脂肪酶B（CAL-B）的酶促水解中使用碳酸钠显示出该脂肪酶的反应性和选择性大大提高。研究了碳酸盐的作用，碱土金属的数量和性质对这种新途径的效率的影响。描述了在温和条件下通过酶促碳酸酯水解产生的乙酸酯1a – 9a的酶促动力学拆分。在所有情况下，所得到的醇和残留的乙酸盐都具有较高的ee值（高达> 99％），而选择性达到E。 > 500。
• 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.