(R)-1-(3-chlorophenyl)ethyl acetate | 136705-69-6

• 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-(3-chlorophenyl)ethyl acetate
• 英文别名: [(1R)-1-(3-chlorophenyl)ethyl] acetate
• CAS: 136705-69-6
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: MHPGGMAHRYXWQV-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙酸异丙烯酯 、 1-(3-氯苯基)乙醇 在 [(η5-1-methoxy-2,4-di-tert-butyl-3-neopentylcyclopentadienyl)Ru(CO)2(CO2Me)] 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以93%的产率得到(R)-1-(3-chlorophenyl)ethyl acetate
  参考文献：
  名称：

  带有钌-脂肪酶对的仲醇的无碱动态动力学拆分。

  摘要：

  我们通过钌催化剂和阴离子表面活性剂激活的脂蛋白脂肪酶的组合报告了各种仲醇的动态动力学拆分（DKR）。在室温下在完全无碱的条件下进行的DKR反应可提供高收率（92-99％）的优异对映体纯度（91-99％ee或更高）的产物。更重要的是，首次以高收率（87-91％）获得了α-芳基烯丙基醇的DKR。

  DOI：

  10.1021/acs.joc.9b02510

文献信息

• Highly efficient dynamic kinetic resolution of secondary aromatic alcohols with low-cost and easily available acid resins as racemization catalysts
  作者：Yongmei Cheng、Gang Xu、Jianping Wu、Chensheng Zhang、Lirong Yang

  DOI：10.1016/j.tetlet.2010.02.152

  日期：2010.4

  A new and efficient dynamic kinetic resolution (DKR) process of secondary aromatic alcohols was developed with acid resins as racemization catalysts. Acid resin CD8604 was shown to have excellent racemization activity and good biocompatibility. When employing CD8604 and complex acyl donors as racemization catalyst and acyl donor, respectively, enantiomerically pure aromatic acetate was obtained with

  以酸性树脂为外消旋催化剂，开发了一种新型高效的仲芳族醇动力学动力学拆分方法。酸性树脂CD8604被证明具有出色的外消旋活性和良好的生物相容性。当分别使用CD8604和复杂的酰基给体作为外消旋催化剂和酰基给体时，通过DKR工艺可获得对映体纯的芳族乙酸酯，且收率和ee值极佳。值得注意的是，该系统可以重复使用10次以上，而产量和ee值的损失很小。
• A Cationic Ruthenium Complex for the Dynamic Kinetic Resolution of Secondary Alcohols
  作者：José A. Fernández-Salas、Simone Manzini、Steven P. Nolan

  DOI：10.1002/chem.201404096

  日期：2014.10.6

  A synthetic protocol making use of a well‐defined cationic ruthenium complex 2 enabling the racemization of enantiomerically pure secondary alcohols in the presence of a weak base (K2CO3) is described. The compatibility of 2 with Candida Antarctica lipase B (Novozym 435) allows the development of an efficient dynamic kinetic resolution of sec‐alcohols in the absence of an additional strong base. This

  描述了利用定义明确的阳离子钌络合物2的合成方案，该阳离子络合物可使对映体纯的仲醇在弱碱（K 2 CO 3）存在下外消旋。2与南极假丝酵母脂肪酶B（Novozym 435）的相容性可在不存在其他强碱的情况下，开发出仲醇的有效动态动力学拆分方法。该方法涉及在阳离子钌催化剂存在下醇的动态动力学拆分的第一个实例。此外，我们描述了单锅反应中酮向富含对映体的乙酸酯的转化，探讨了复合物2的多功能性。
• Stereochemistry and Mechanism of Enzymatic and Non-Enzymatic Hydrolysis of Benzylic<i>sec</i>-Sulfate Esters
  作者：Michael Toesch、Markus Schober、Rolf Breinbauer、Kurt Faber

  DOI：10.1002/ejoc.201402211

  日期：2014.6

  The substrate scope of inverting alkylsulfatase Pisa1 was extended towards benzylic sec-sulfate esters by suppression of competing non-enzymatic autohydrolysis by addition of dimethyl sulfoxide as co-solvent. Detailed investigation of the mechanism of autohydrolysis in 18O-labeled buffer by using an enantiopure sec-benzylic sulfate ester as substrate revealed that from the three possible pathways (i)

  通过添加二甲基亚砜作为助溶剂，抑制竞争性非酶自水解作用，将烷基硫酸酯酶Pisa1转化的底物范围扩展至苄基仲硫酸酯。以对映体纯的仲苄基硫酸酯为底物，在18O标记的缓冲液中自动水解机理的详细研究表明，从三个可能的途径（i）[SN-] [OH-]的SN2型亲核攻击在苄基碳上的转化代表：主要途径，（ii）导致消旋化的平面苄基碳正离子的SN1型形成是次要事件，并且（iii）在检测极限处发生了对硫的SN2型亲核攻击的保留。通过分析间位取代基的哈米特常数解释所获得的数据。
• 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.
• Baeyer–Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters
  作者：Cristina Rodríguez、Gonzalo de Gonzalo、Daniel E. Torres Pazmiño、Marco W. Fraaije、Vicente Gotor

  DOI：10.1016/j.tetasy.2009.03.018

  日期：2009.6

  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.