(S)-1-(4-methoxyphenyl)ethyl acetate

• 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: (S)-1-(4-methoxyphenyl)ethyl acetate
• 英文别名: 1-(4-methoxyphenyl)ethyl acetate；[(1S)-1-(4-methoxyphenyl)ethyl] acetate
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: ULIOGACDIOOFPE-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (S)-1-(4-methoxyphenyl)ethyl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (S)-(-)-对甲氧基苯乙醇
  参考文献：
  名称：

  一种高选择性的酯水解酶从假单胞菌。用于酶法制备对映体纯的仲醇；有机合成中的手性助剂

  摘要：

  一系列有价值的手性助剂（R）-和（S）-（1）-（11），通过在假单胞菌属脂肪酶的脂肪酶存在下酶解其酯，以高化学和光学收率制备。

  DOI：

  10.1039/c39880000598
• 作为产物：
  描述：

  4-甲氧基-α-甲基苯甲醇 在 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 aq. phosphate buffer 、 乙醚 为溶剂， 反应 72.0h， 生成 (S)-1-(4-methoxyphenyl)ethyl acetate
  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

• Synthesis of Chiral Hydroxyl Phospholanes from <scp>d</scp>-mannitol and Their Use in Asymmetric Catalytic Reactions
  作者：Wenge Li、Zhaoguo Zhang、Dengming Xiao、Xumu Zhang

  DOI：10.1021/jo000066c

  日期：2000.6.1

  Strategies for protection and deprotection of OH-groups in the presence of phosphines have been explored. Rate acceleration in the Baylis-Hillman reaction was observed when a hydroxyl phosphine was used as the catalyst. Rhodium complexes with chiral bisphospholanes are highly enantioselective catalysts for the asymmetric hydrogenation of various kinds of functionalized olefins such as dehydroamino

  手性羟基一膦3 [（2S，3S，4S，5S）-3,4-二羟基-2，5-二甲基-1-苯基膦烷]和双膦酸酯5a [1,2-双[（2S，3S，4S，5S） -3,4-二羟基-2,5-二甲基磷杂环戊烷基]苯]和5b [1,2-双[（2S，3S，4S，5S）-2,5-二乙基-3,4-二羟基磷杂环戊基]苯]从现成的D-甘露醇中以高收率获得。已经研究了在膦存在下保护和脱保护OH-基团的策略。当使用羟基膦作为催化剂时，在Baylis-Hillman反应中观察到速率加速。铑与手性双膦酸酯的络合物是高度对映选择性的催化剂，用于各种官能化烯烃（如脱氢氨基酸衍生物，衣康酸衍生物和烯酰胺）的不对称氢化。
• DMSO-triggered enhancement of enantioselectivity in Novozyme[435]-catalyzed transesterification of chiral 1-phenylethanols
  作者：Amrit Goswami、Jonali Goswami

  DOI：10.1016/j.tetlet.2005.03.147

  日期：2005.6

  Dimethyl sulfoxide as cosolvent enhances the enantioselectivity of resolved products up to 100% in the Novozyme[435]-catalyzed transesterification of chiral 1-phenylethanols but not 1-phenyl-2-haloethanols in THF. The reaction does not proceed in lipophilic and water-miscible polar solvents.

  二甲基亚砜作为助溶剂，在Novozyme [435]催化的手性1-苯基乙醇（而非1-苯基-2-卤代乙醇）在THF中的酯交换反应中，可将拆分产物的对映选择性提高至100％。该反应不会在亲脂性和水混溶性极性溶剂中进行。
• Selection of Enantioselective Acyl Transfer Catalysts from a Pooled Peptide Library through a Fluorescence-Based Activity Assay:  An Approach to Kinetic Resolution of Secondary Alcohols of Broad Structural Scope
  作者：Gregory T. Copeland、Scott J. Miller

  DOI：10.1021/ja0108584

  日期：2001.7.1

  new class of octapeptide catalysts for the kinetic resolution of secondary alcohols. A highly diverse library of peptide-based catalysts was synthesized on solid-phase synthesis beads such that each individual bead was co-functionalized with (i) a uniform loading of a pH-sensitive fluorophore and (ii) a unique peptide-based catalyst. The library was then screened for activity in acylation reactions employing

  使用荧光标记的分裂和池肽库的分析已被应用于发现一类新的八肽催化剂，用于二级醇的动力学分辨率。在固相合成珠上合成了高度多样化的基于肽的催化剂库，使每个单独的珠与 (i) 均匀负载 pH 敏感荧光团和 (ii) 独特的基于肽的催化剂共功能化。然后在使用(+/-)-sec-苯基乙醇作为底物和乙酸酐作为酰化剂的酰化反应中筛选文库的活性。从最活跃的催化剂中，鉴定出一种铅肽 (4)，在均质条件下进行再合成和评估时，其提供的选择性因子 (k(rel)) 为 8.2。一个“定向” 合成了第二代分裂和合并肽库，使得库中的新肽序列偏向于先导结构。第二代文库的随机样本在单珠分析中进行了筛选，揭示了几种新的基于肽的催化剂，这些催化剂在动力学分辨率方面提供了改进的选择性。肽催化剂 13 证明对 sec-苯基乙醇 (k(rel) = 20) 以及广泛底物范围 (k(rel) = 4 至 > 50) 的其他八种二级醇的动力学分辨率有效。
• <b>PQXdpap</b>: Helical Poly(quinoxaline-2,3-diyl)s Bearing 4-(Dipropylamino)pyridin-3-yl Pendants as Chirality-Switchable Nucleophilic Catalysts for the Kinetic Resolution of Secondary Alcohols
  作者：Takeshi Yamamoto、Ryo Murakami、Michinori Suginome

  DOI：10.1021/acs.orglett.1c03134

  日期：2021.11.19

  Helically chiral poly(quinoxaline-2,3-diyl)s bearing 4-(dipropylamino)pyridin-3-yl pendants at the 5-position of the quinoxaline ring (PQXdpap) exhibited high catalytic activities and moderate to high selectivities (up to s = 87) in the acylative kinetic resolution of secondary alcohols. The solvent-dependent helical chirality switching of PQXdpap between pure toluene and a 1:1 mixture of toluene and

  在喹喔啉环 ( PQXdpap )的 5 位带有 4-(二丙氨基) 吡啶-3-基侧链的螺旋手性聚 (quinoxaline-2,3-diyl)s表现出高催化活性和中到高选择性（高达s = 87) 在仲醇的酰化动力学拆分中。PQXdpap在纯甲苯和 1:1 的甲苯和 1,1,2-三氯乙烷混合物之间的溶剂依赖性螺旋手性转换能够从单一催化剂。
• Practical P-Chiral Phosphane Ligand for Rh-Catalyzed Asymmetric Hydrogenation
  作者：Duan Liu、Xumu Zhang

  DOI：10.1002/ejoc.200400690

  日期：2005.2

  conformationally rigid P-chiral bis(trialkylphospholane) ligand 2 (DuanPhos) has been prepared in both enantiomeric forms through a concise syn-thesis. Rh-2 complex has exhibited remarkably high enantio-selectivities (up to >99% ee) and reactivities (up to 10,000 TON) for the hydrogenation of a wide variety of functionalized prochiral alkenes (5 different types), which provides a very practical catalytic system

  已经通过简洁的合成以两种对映体形式制备了高度供电子和构象刚性 P-手性双（三烷基磷烷）配体 2 (DuanPhos)。Rh-2 络合物对多种官能化前手性烯烃（5 种不同类型）的氢化表现出非常高的对映选择性（高达 99% ee）和反应性（高达 10,000 吨），提供了一种非常实用的催化用于制备各种合成有用的手性化合物的系统。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)