(+/-)-1-(3-methylphenyl)ethyl acetate | 19759-22-9

• 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-methylphenyl)ethyl acetate
• 英文别名: Essigsaeure-1-(m-tolyl)-ethylester；1-(3-Methyl-phenyl)-ethyl-acetat；1-(3-Methylphenyl)ethyl-acetat；1-(3-Methylphenyl)ethyl acetate
• CAS: 19759-22-9
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: OJQQEFVVFXXONI-UHFFFAOYSA-N

物化性质

• 沸点：
  231.1±9.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(3-methylphenyl)ethyl acetate 生成 (S)-1-(3-methylphenyl)ethyl acetate
  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：

  (+/-)-3-(3-methylphenyl)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-methylphenyl)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

• Copper(II) Triflate as a Double Catalyst for the One-Pot Click Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Benzylic Acetates
  作者：Shin-ichi Fukuzawa、Eiji Shimizu、Satoshi Kikuchi

  DOI：10.1055/s-2007-986638

  日期：2007.9

  Copper(II) triflate doubly catalyzed the substitution of benzylic acetates by TMSN3 and the subsequent 1,3-dipolar addition with an alkyne in one pot. This procedure afforded the preparation of 1,4-disubstituted 1,2,3-triazoles in good yields starting from the easily accessible acetates without isolating an organic azide ­using a single catalyst.

  铜(II)三氟甲磺酸盐双重催化苄基乙酸酯与TMSN3的取代反应，以及随后与炔烃的一锅法1,3-偶极加成反应。该过程以良好产率制备了易于获得的乙酸酯为起始物，无需分离有机叠氮化合物，仅使用单一催化剂即可合成1,4-二取代的1,2,3-三唑。
• Fungal mediated kinetic resolution of racemic acetates to ( R )-alcohols using Fusarium proliferatum
  作者：Dipesh D. Jadhav、Harshal S. Patil、Patil S. Chaya、Hirekodathakallu V. Thulasiram

  DOI：10.1016/j.tetlet.2016.08.084

  日期：2016.10

  Fungal mediated kinetic resolution of seven acyclic/aromatic acetates was achieved using Fusarium proliferatum to furnish (R)-alcohols in high enantiomeric excess (>95%). The kinetic resolution was established as one-pot two-step de-esterification/oxidation biocatalytic process. Further, the preparative scale synthesis of (R)-(+)-1-phenylethanol was accomplished through de-esterification/oxidation

  使用枯萎镰刀菌（Fusarium proliferatum）提供对映体过量（> 95％）的（R）醇可达到真菌介导的七个无环/芳族乙酸酯的动力学拆分。动力学拆分被确定为一锅两步脱酯/氧化生物催化过程。此外，（的制备规模合成- [R ）- （+） - 1-苯基乙醇通过（±）脱酯化/氧化反应完成使用的全细胞-1-苯乙基乙酸酯F. proliferatum NCIM 1105。
• Entrapment of Pseudomonas cepacia lipase with peracetylated β-cyclodextrin in sol–gel: application to the kinetic resolution of secondary alcohols
  作者：Ashraf Ghanem、Volker Schurig

  DOI：10.1016/s0957-4166(03)00550-0

  日期：2003.9

  cepacia lipase with peracetylated β-cyclodextrin was immobilized by the sol–gel process. The gel-entrapped lipase/cyclodextrin was prepared by the hydrolysis of methyltrimethoxysilane (MTMS) in the presence of the co-lyophilized lipase with peracetylated β-cyclodextrin prepared with different weight ratios (enzyme to CD). This type of enzyme preparation was subsequently used in the kinetic resolution

  共冻干洋葱假单胞菌过乙酰化β-环糊精的脂肪酶通过溶胶-凝胶法固定化。凝胶包裹的脂肪酶/环糊精是在共冻干脂肪酶与过乙酰化的β-环糊精共存的条件下，通过甲基三甲氧基硅烷（MTMS）的水解而制得的，所述过乙酰化的β-环糊精以不同的重量比（酶与CD）制备。这种类型的酶制剂随后用于动力学拆分一组仲醇，其中乙酸异丙烯酯作为甲苯中无害的酰基供体，作为有机介质。使用气相色谱法在新的手性固定相（CSP）Chirasil-β-Dex上含有十一碳亚甲基间隔基（C11-Chirasil-Dex）的情况下，在不进行衍生化的情况下，将分析中得到的手性醇（底物）和相应的乙酸盐（产物）进行基线分离。 。
• BVMO-catalysed dynamic kinetic resolution of racemic benzyl ketones in the presence of anion exchange resins
  作者：Cristina Rodríguez、Gonzalo de Gonzalo、Ana Rioz-Martínez、Daniel E. Torres Pazmiño、Marco W. Fraaije、Vicente Gotor

  DOI：10.1039/b922693a

  日期：——

  fluorescens ACB was employed in the presence of a weak anion exchange resin to perform dynamic kinetic resolutions of racemic benzyl ketones with high conversions and good optical purities. Different parameters that affect to the efficiency of the enzymatic Baeyer–Villiger oxidation and racemisation were analyzed in order to optimize the activity and selectivity of the biocatalytic system.

  4-羟基苯乙酮来自荧光假单胞菌ACB的单加氧酶在弱阴离子交换树脂的存在下用于以高转化率和良好的光学纯度进行外消旋苄基酮的动态动力学拆分。为了优化生物催化系统的活性和选择性，分析了影响酶催化的拜耳-维利格氧化和外消旋化效率的不同参数。
• 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。