(-)-(R)-2-bromo-1-phenyl-1-acetoxyethane | 73908-24-4

• 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: (-)-(R)-2-bromo-1-phenyl-1-acetoxyethane
• 英文别名: (R)-1-bromo-2-acetoxy-2-(phenyl)ethane；(R)-2-bromo-1-phenylethyl acetate；Benzenemethanol, I+/--(bromomethyl)-, 1-acetate, (I+/-R)-；[(1R)-2-bromo-1-phenylethyl] acetate
• CAS: 73908-24-4
• 化学式: C₁₀H₁₁BrO₂
• 分子量: 243.1
• InChiKey: HYZUUGCDDLLYSL-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 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：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (-)-(R)-2-bromo-1-phenyl-1-acetoxyethane 、 氢氧化钾 以78%的产率得到
  参考文献：
  名称：

  IMUTA M.; KAWAI KEN-ICHI; ZIFFER H., J. ORG. CHEM., 1980, 45, NO 16, 3352-3355

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴苯乙酮 以 吡啶 、 水 为溶剂， 反应 178.0h， 生成 (-)-(R)-2-bromo-1-phenyl-1-acetoxyethane
  参考文献：
  名称：

  Product stereospecificity in the microbial reduction of .alpha.-haloaryl ketones

  摘要：

  DOI：

  10.1021/jo01304a044

文献信息

• Lipase mediated enzymatic kinetic resolution of phenylethyl halohydrins acetates: A case of study and rationalization
  作者：Thiago de Sousa Fonseca、Kimberly Benedetti Vega、Marcos Reinaldo da Silva、Maria da Conceição Ferreira de Oliveira、Telma Leda Gomes de Lemos、Martina Letizia Contente、Francesco Molinari、Marco Cespugli、Sara Fortuna、Lucia Gardossi、Marcos Carlos de Mattos

  DOI：10.1016/j.mcat.2020.110819

  日期：2020.4

  light on the different reaction rates, docking studies were carried out with all the substrates using MD simulations. The computational data obtained for the β-brominated substrates, based on the parameters analysed such as NAC (near attack conformation), distance between Ser-O and carbonyl-C and oxyanion site stabilization were in agreement with the experimental results. On the other hand, the data

  在来自南极假丝酵母的脂肪酶B （435）的存在下，通过水解反应将含有与芳香环相连的多个基团的外消旋苯乙基卤代醇乙酸酯分解。在所有情况下，动力学拆分都是高度选择性的（E> 200），导致相应的拆分（See> 99％的）-β-卤代醇。但是，理想的50％转化所需的时间为2,4-二氯苯基氯醇乙酸盐的15分钟到2-氯苯基溴醇乙酸盐的216小时。评价了六种氯醇和五种溴醇，后者的反应性较低。对于β-溴化的底物，芳香环上的位阻起着至关重要的作用，而对于β-氯代衍生物则没有观察到。为了阐明不同的反应速率，使用MD模拟对所有底物进行了对接研究。基于分析的参数（例如NAC（近攻构象），Ser-O与羰基-C之间的距离和氧阴离子位点稳定化）获得的有关β-溴化底物的计算数据与实验结果相符。另一方面，
• Immobilization of Amano lipase from Pseudomonas fluorescens on silk fibroin spheres: an alternative protocol for the enantioselective synthesis of halohydrins
  作者：Irlon M. Ferreira、Sergio A. Yoshioka、João V. Comasseto、André L. M. Porto

  DOI：10.1039/c7ra00083a

  日期：——

  for a new, efficient, cheaper and sustainable matrix for lipase immobilization is a growing area in biotechnology. Amano lipase from Pseudomonas fluorescens was immobilized on silk fibroin spheres and used in the enzymatic kinetic resolution of halohydrins, to obtain optically active epoxides (up to 99% ee), important precursors in the synthesis of derivative antifungal azoles. This paper reinforces

  寻找一种新的，有效的，便宜的和可持续的脂肪酶固定基质是生物技术领域的一个增长领域。将荧光假单胞菌的天冬脂酶固定在丝素蛋白球上，并用于卤代醇的酶促动力学拆分，以获得旋光性环氧化物（高达99％ee），这是衍生的抗真菌唑合成中的重要前体。本文增强了丝素蛋白作为多相催化剂载体的多功能性。
• Kinetic resolution of a drug precursor by Burkholderia cepacia lipase immobilized by different methodologies on superparamagnetic nanoparticles
  作者：Leandro H. Andrade、Lya P. Rebelo、Caterina G.C.M. Netto、Henrique E. Toma

  DOI：10.1016/j.molcatb.2010.03.002

  日期：2010.9

  Burkholderia cepacia lipase was immobilized on superparamagnetic nanoparticles using three different methodologies (adsorption, chemisorption with carboxibenzaldehyde and chemisorption with glutaraldehyde) and employed in the kinetic resolution of a chiral drug precursor, (RS)-2-bromo-1-(phenyl)ethanol, via enantioselective acetylation reaction. An excellent improvement of lipase catalytical performance was observed. Free B. cepacia lipase gave the ester (S)-2 with poor E-value <30, and after its immobilization to magnetic nanoparticles the E-value was up to >200. The effect of several reaction parameters in the kinetic resolution was studied. The best results for kinetic resolution were obtained using vinyl acetate as acetyl donor and toluene as solvent, typically yielding the ester in high enantiomeric excess (>99%) and E-value (E > 200). Of the three tested immobilization methods, chemisorption with glutaraldehyde was the best one in terms of temperature stability and yield product. (C) 2010 Elsevier B.V. All rights reserved.
• KAJIGAESHI, SHOJI;KAKINAMI, TAKAAKI;MORIWAKI, MASAYUKI;FUJISAKI, SHIZUO;T+, KYUSYU DAJGAKU KINO BUSSITSU KAGAKU KEHNKYUDZE XOKOKU, 2,(1988) N, S. 87-+
  作者：KAJIGAESHI, SHOJI、KAKINAMI, TAKAAKI、MORIWAKI, MASAYUKI、FUJISAKI, SHIZUO、T+

  DOI：——

  日期：——