(+/-)-1-(3-methoxyphenyl)ethyl acetate | 93351-40-7

• 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: (+/-)-1-(3-methoxyphenyl)ethyl acetate
• 英文别名: 1-(3-methoxyphenyl)ethyl acetate
• CAS: 93351-40-7
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: CXOKJNFDHYCTAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  257.0±23.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

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：

  (+/-)-1-(3-methoxyphenyl)ethyl acetate 在 水 作用下， 反应 72.0h， 生成 (S)-1-(3-甲氧基苯基)乙醇 、 (1R)-1-(3-甲氧基苯基)乙醇
  参考文献：
  名称：

  阿魏根霉的生物转化：1-苯基乙醇与1-（fo-，m-和对-甲氧基苯基）乙醇的对映体的制备

  摘要：

  真菌少根根霉已经用于苯乙酮的还原和其ö - ，米-和p -甲氧基衍生物1A-d到相应的（小号） - （ - ） -醇。它们的外消旋乙酸酯也水解为（R）-（+）-醇。产品的分析表明可以使用以下获得的对映体选择性最大（78-88％ee）的米-甲氧基苯乙酮作为底物。

  DOI：

  10.1016/0957-4166(95)00304-8
• 作为产物：
  描述：

  3-(3-methoxyphenyl)butan-2-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 (+/-)-1-(3-methoxyphenyl)ethyl acetate
  参考文献：
  名称：

  Baeyer–Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters

  摘要：

  The application of three BVMOs for the enantioselective oxidation of 3-phenylbutan-2-ones with different substituents in the aromatic moiety is described. By choosing the appropriate biocatalyst and substrate combination, chiral ketones and esters can be obtained with excellent enantiopurities. This methodology could also be applied to the resolution of racemic alpha-alkyl benzylketones with longer alkyl chains as well as with two substituted alpha-substituted benzylacetones. A kinetic analysis revealed that the BVMOs studied effectively convert all tested compounds showing that the enzymes are tolerant towards the substrate structure while being highly enantioselective. These properties render BVMOs as valuable biocatalysts for the preparation of compounds with high interest in organic synthesis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.018

文献信息

• Concerted bimolecular substitution reactions of 1-phenylethyl derivatives
  作者：John P. Richard、William P. Jencks

  DOI：10.1021/ja00317a033

  日期：1984.3

  Etude des proprietes des reactions de substitution bimoleculaire des derives aryl-1 ethyles avec l'azoture et d'autres reactifs nucleophiles

  Etude des proprietes des反应去取代双分子衍生芳基-1 乙基酯 avec l'azoture et d'autres reactifs 亲核试剂
• Chemoenzymatic Synthesis of Rivastigmine Based on Lipase-Catalyzed Processes
  作者：Juan Mangas-Sánchez、María Rodríguez-Mata、Eduardo Busto、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1021/jo900784g

  日期：2009.8.7

  straightforward chemoenzymatic synthesis of enantiomerically pure rivastigmine has been efficiently carried out under mild reaction conditions, with Candida antarctica lipase B responsible for the stereoselective acetylation of the corresponding (R)-alcohol or amine. An exhaustive enzymatic study has been developed exploring the possibilities of carry out enzyme recycling, scaling up the enzymatic process and

  对映体纯的利凡斯的明的简单化学化学合成已经在温和的反应条件下有效地进行，南极假丝酵母脂肪酶B负责相应的（R）-醇或胺的立体选择性乙酰化。已经进行了详尽的酶学研究，探索了进行酶循环利用，扩大酶促工艺和开发动态动力学拆分程序以生产足够的对映体纯的利凡斯的明前体的可能性。从可商购的3-甲氧基苯乙酮以良好的总产率进行了该药物的总化学酶促合成。
• Separation of enantiopure m-substituted 1-phenylethanols in high space-time yield using Bacillus subtilis esterase
  作者：Gao-Wei Zheng、Xu-Yun Liu、Zhi-Jun Zhang、Ping Tian、Guo-Qiang Lin、Jian-He Xu

  DOI：10.1039/c3ra41999a

  日期：——

  A recombinant Bacillus subtilis esterase (BsE) expressed in E. coli was found to exhibit excellent enantioselectivity (E was always greater than 100) towards m-substituted 1-phenylethanol acetates in the enantioselective hydrolysis reaction. An explanation for the high enantioselectivity observed towards these substrates was provided by molecular modeling. Moreover, the BsE also showed strong tolerance towards a high concentration of m-substituted 1-phenylethanol acetates (up to 1 M). Based on these excellent catalytic properties of BsE, a kind of m-substituted 1-phenylethanols, (R)-1-(3-chlorophenyl)ethanol, was efficiently synthesized in space-time yield of 920 g per L per day and 97% ee, indicating that the BsE was considered as a potentially ideal and promising biocatalyst for large-scale production of optically active m-substituted 1-phenylethanols.

  研究发现，在大肠杆菌中表达的重组枯草芽孢杆菌酯酶（BsE）在对映选择性水解反应中对 m-取代的 1-苯基乙醇乙酸酯表现出极好的对映选择性（E 始终大于 100）。分子模型为观察到的对这些底物的高对映选择性提供了解释。此外，BsE 还对高浓度的间取代 1-苯基乙醇乙酸酯（高达 1 M）表现出很强的耐受性。基于 BsE 的这些优异催化特性，一种间代 1-苯基乙醇--(R)-1-(3-氯苯基)乙醇被高效合成，时空产率为 920 克/升/天，ee 为 97%，这表明 BsE 被认为是大规模生产具有光学活性的间代 1-苯基乙醇的一种潜在的理想和有前途的生物催化剂。
• Immobilized Manihot esculenta preparation as a novel biocatalyst in the enantioselective acetylation of racemic alcohols
  作者：Luciana L. Machado、Telma L.G. Lemos、Marcos Carlos de Mattos、Maria da Conceicão F. de Oliveira、Gonzalo de Gonzalo、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1016/j.tetasy.2008.05.018

  日期：2008.6

  The enzymatic preparation obtained from a discard of Manihot esculenta roots has been successfully immobilized on calcium alginate hydrogels. This preparation has been tested as a chiral biocatalyst in the enzymatic acylation of a set of racemic aromatic alcohols. Depending on the reaction conditions, excellent enantioselectivities can be achieved. Some parameters that can alter the biocatalytic properties of the enzyme, such as solvent, temperature, acyl donor and substrate structure have been studied exhaustively in order to establish a deeper knowledge of this novel biocatalyst. (C) 2008 Elsevier Ltd. All rights reserved.
• Asymmetric transesterification of secondary alcohols catalyzed by feruloyl esterase from Humicola insolens
  作者：Nikos S. Hatzakis、Ioulia Smonou

  DOI：10.1016/j.bioorg.2005.05.002

  日期：2005.8

  A new asymmetric transesterification of secondary alcohols catalyzed by feruloyl esterase from Humicola insolens has been found. Although alcohols are not the natural substrates for this enzyme, a high R enantioselectivity was observed. Stereochemical studies showed that variations in substrate structure lead to strong variations in enantioselectivity. The highest enantioselectivities are obtained when the beta-carbon of the secondary alcohol is tertiary or quaternary. (c) 2005 Elsevier Inc. All rights reserved.