[(2R)-1-phenylpropan-2-yl] butanoate | 118295-00-4

• 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: [(2R)-1-phenylpropan-2-yl] butanoate
• CAS: 118295-00-4
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: ANJRGSHRMWLHFZ-LLVKDONJSA-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

• 作为反应物：
  描述：

  [(2R)-1-phenylpropan-2-yl] butanoate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 (R)-1-苯基-2-丙醇
  参考文献：
  名称：

  Kinetic and chemical resolution of different 1-phenyl-2-propanol derivatives

  摘要：

  Seven chiral target molecules containing a hydroxy group have been resolved by both biocatalytic and chemical means. The lipase-catalyzed acylation mainly yielded the acylated derivative of the (R)-alcohols with moderate enantiomeric excess and the enantiopure (S)-alcohols. In the course of the chemical resolution, first the dicarboxylic acid monoesters of the target molecules were synthesized and the resolution of these monoesters was attempted by different homochiral bases. By re-resolution and/or optimization of the reaction time and/or recrystallization, respectively, each molecule was produced in very high enantiomeric purity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.019
• 作为产物：
  描述：

  正丁酸乙烯酯 、 1-苯基-2-丙醇 在 lipase from Sporisorium reilianum SRZ₂ immobilized on Celite 作用下， 以 甲基叔丁基醚 为溶剂， 反应 44.0h， 以99%的产率得到
  参考文献：
  名称：

  测量两种南极念珠菌-脂肪酶-B 同系物对手性 sec -醇的对映选择性

  摘要：

  DOI：

  10.1002/bkcs.11289

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。
• Discovery and Redesign of a Family VIII Carboxylesterase with High (<i>S</i>)-Selectivity toward Chiral <i>sec</i>-Alcohols
  作者：Areum Park、Seongsoon Park

  DOI：10.1021/acscatal.1c05410

  日期：2022.2.18

  Furthermore, the (S)-selectivity of PBE has been significantly improved by rational redesign based on molecular modeling. Molecular modeling identified a binding pocket composed of Ser381, Ala383, and Arg408 for the methyl substituent of (R)-1-phenylethyl acetate and suggested that larger residues may increase the enantioselectivity by interfering with the binding of the slow-reacting enantiomer. As predicted

  高度对映选择性脂肪酶已广泛用于通过动力学或动态动力学拆分制备通用的对映纯手性仲醇。脂肪酶本质上是( R )-选择性的，很难获得( S )-选择性脂肪酶。VIII 族羧酸酯酶的最新晶体结构表明，其催化三联体的空间阵列是脂肪酶的镜像，但催化三联体不同于脂肪酶。因此，我们假设 VIII 族羧酸酯酶可能对类似于 ( S ) 的仲醇表现出( S )-对映选择性。)-选择性丝氨酸蛋白酶，其催化三联体也在空间上排列为它的镜像。在这项研究中，制备了一种已知家族 VIII 羧酸酯酶（pdb 代码：4IVK）的同源酶（来自变形杆菌SG_bin9 的羧酸酯酶，PBE），该酶不仅对3-丁炔等仲醇具有中等的 ( S )-选择性。-2-醇和1-苯乙醇以及( R )-对所探索的底物中特定仲醇的选择性。此外，（S)-PBE 的选择性已通过基于分子模型的合理重新设计显着提高。分子模型确定了一个由 Ser381、Ala383
• 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.
• Mapping the Substrate Selectivity of Novel Lipase from<i>Pseudozyma hubeiensis</i>SY62
  作者：Seongsoon Park

  DOI：10.1002/bkcs.10918

  日期：2016.10