butyric acid-((S)-1-methyl-2-phenyl-ethyl ester) | 221911-67-7

• 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: butyric acid-((S)-1-methyl-2-phenyl-ethyl ester)
• 英文别名: Buttersaeure-((S)-1-methyl-2-phenyl-aethylester)；[(2S)-1-phenylpropan-2-yl] butanoate
• CAS: 221911-67-7
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: ANJRGSHRMWLHFZ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  正丁酸2,2,2-三氟乙酯 、 1-苯基-2-丙醇 在 aminocyclopentadienylruthenium surfacant-treated subtilisin 、 potassium tert-butylate 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以89%的产率得到butyric acid-((S)-1-methyl-2-phenyl-ethyl ester)
  参考文献：
  名称：

  (S)-Selective Dynamic Kinetic Resolution of Secondary Alcohols by the Combination of Subtilisin and an Aminocyclopentadienylruthenium Complex as the Catalysts

  摘要：

  A new procedure for the dynamic kinetic resolution (DKR) of racemic alcohols into single enantiomers is described. This procedure employs surfactant-treated subtilisin as an (S)-selective resolving catalyst and an aminocyclopentadienylruthenium complex as a racemizing catalyst. The DKR is performed best in the presence of an acyl donor such as trifluoroethyl butyrate in THF at room temperature. Eight simple secondary alcohols have been efficiently resolved with high optical purities and good yields. The subtilisin-based DKR is complementary in stereoselectivity to its lipase-based counterpart. For an acyl-carrying alcohol, both subtilisin- and lipase-based DKRs have proceeded equally well to give a pair of enantiomeric products (>99.5% ee each) with opposite optical rotations in high yields (94-95%).

  DOI：

  10.1021/ja036766r

文献信息

• Dual enzymatic dynamic kinetic resolution by Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase and Candida antarctica lipase B
  作者：Ibrahim Karume、Musa M. Musa、Odey Bsharat、Masateru Takahashi、Samir M. Hamdan、Bassam El Ali

  DOI：10.1039/c6ra18895h

  日期：——

  showed that this racemization approach in organic solvent was compatible with Candida antarctica lipase B (CALB)-catalyzed kinetic resolution. This compatibility, therefore, allowed a dual enzymatic dynamic kinetic resolution of racemic alcohols using CALB-catalyzed kinetic resolution and W110A TeSADH-catalyzed racemization of phenyl-ring-containing alcohols.

  溶胶-凝胶法固定化乙醇嗜热厌氧菌仲醇脱氢酶（TeSADH）使其可以在有机介质中外消旋对映纯醇。在这里，我们报道了使用干凝胶固定的W110A TeSADH在己烷中而不是在酶所需的水性介质中消旋对映体纯的含苯环的仲醇。我们进一步表明，这种在有机溶剂中的消旋方法与南极假丝酵母脂肪酶B（CALB）催化的动力学拆分相容。因此，这种相容性允许使用CALB催化的动力学拆分和W110A TeSADH催化的含苯环的醇的消旋化作用，使消旋醇具有双重酶促动力学拆分。
• Fatty and aromatic acids as acyl donors in enzymatic kinetic resolution of phenylethanol and 1-phenylpropan-2-ol
  作者：Fatma Zohra Smaine、Mounia Merabet-Khelassi、Saoussen Zeror、Emilie Kolodziej、Martial Toffano、Louisa Aribi-Zouioueche

  DOI：10.1007/s00706-023-03147-3

  日期：2024.1

  The use of fatty and aromatic acids as green acyl donors for enzymatic kinetic resolution via esterification of 1-phenylethanol and 1-phenylpropan-2-ol was described. The impact of the presence of magnesium sulfate on both reactivity and selectivity of Candida rugosa lipase (CRL) was checked. The organic solvents, the medium dilution, and the temperature revealed as determinant parameters to achieve

  描述了使用脂肪酸和芳香酸作为绿色酰基供体，通过 1-苯基乙醇和 1-苯基丙-2-醇的酯化进行酶动力学拆分。检查了硫酸镁的存在对假丝酵母脂肪酶 (CRL)的反应性和选择性的影响。有机溶剂、介质稀释度和温度是实现对映选择性酯化反应的决定性参数。在使用丁酸和月桂酸作为酰基供体拆分 1-苯基乙醇过程中，硫酸镁的使用对庚烷中 CRL 的对映选择性产生了显着影响。 图形概要
• Enzyme reactions in apolar solvents. The resolution of branched and unbranched 2-alkanols by porcine pancreatic lipase.
  作者：Brian Morgani、Allan C. Oehlschlager、Thomas M. Stokes

  DOI：10.1016/s0040-4020(01)96905-4

  日期：1991.1

  Straight-chain and branched 2-alkanols were subjected to enzyme catalyzed transesterification in organic solvent using porcine pancreatic lipase, high enantioselectivity being generally observed. The method was applied to the synthesis of (R)-(-)-9-hydroxy-(E)-decenoic acid, a component of the queen bee mandibular gland pheromone.
• Functional expression of Serratia marcescens H30 lipase in Escherichia coli for efficient kinetic resolution of racemic alcohols in organic solvents
  作者：Erzheng Su、Jingjing Xu、Pengyong You

  DOI：10.1016/j.molcatb.2014.04.012

  日期：2014.8

  A lipase from Serratia marcescens H30 was cloned and functionally expressed in E. coli in soluble form (more than 80%). The recombinant lipase activity reached 25,000 U/L after optimization. Different carriers were used to immobilize the recombinant S. marcescens lipase (SmL), and LH-EP was found to be the most ideal carrier. LH-EP immobilized SmL could catalyze enantioselective resolution of racemic alcohols. Using 4-phenyl-2-butanol as the model alcohol, the effects of temperature, organic solvent, water activity, acyl donor and substrate molar ratio on the LH-EP immobilized SmL catalyzed kinetic resolution were investigated. All of these factors influenced the resolution effect to some extent. At last, a high E value of more than 200 was achieved, with ee(s) > 99% and a conversion of 49.9%. Further studies showed that the LH-EP immobilized SmL could also catalyze the kinetic resolution of other structure similar racemic alcohols. These results indicate that the SmL is useful for biocatalytic production of chiral alcohols. This work is the first attempt of using SmL in this field, and it further broadens the application field of SmL. (C) 2014 Elsevier B.V. All rights reserved.
• Activity enhancement of pig liver esterase in organic solvents by colyophilization with methoxypolyethylene glycol: kinetic resolution of alcohols
  作者：Stephan Ruppert、Hans-Joachim Gais

  DOI：10.1016/s0957-4166(97)00469-2

  日期：1997.11

  Colyophilization of pig liver esterase with methoxypolyethylene glycol gave a catalyst, PLE/MPEG, which showed an enhanced activity in organic solvents. The PLE/MPEG catalyzed transesterification of the alcohols rac-1a-d with vinyl propionate in toluene proceeded with good to high selectivities. The addition of up to 1% of water to the reaction mixture resulted in a significant increase in enantioselectivity. Immobilization of PLE/MPEG for the batch-wise resolution was accomplished by its spontaneous adsorption on an ultrafiltration membrane. (C) 1997 Elsevier Science Ltd.