(S)-2-溴-1-(2-氯苯基)乙烷-1-醇 | 1212322-23-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-2-溴-1-(2-氯苯基)乙烷-1-醇
• 英文名称: 2-bromo-1-(2-chlorophenyl)ethan-1-ol
• 英文别名: (1S)-2-bromo-1-(2-chlorophenyl)ethan-1-ol；(1S)-2-bromo-1-(2-chlorophenyl)ethanol
• CAS: 1212322-23-0
• 化学式: C₈H₈BrClO
• mdl: MFCD09863582
• 分子量: 235.508
• InChiKey: ZASGHPFWAAEKAD-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  叔丁胺 、 (S)-2-溴-1-(2-氯苯基)乙烷-1-醇 以 乙腈 为溶剂， 生成 tulobuterol
  参考文献：
  名称：

  METHODS FOR TREATING VARIOUS CONDITIONS AND INDICATIONS WITH AGONISTS AND ANTAGONISTS

  摘要：

  In various aspects and embodiments provided are compositions and methods for identifying subjects in need of improving cognition and/or treating a neurodegenerative disease in a subject and treating such subject. More specifically, the disclosure in some embodiments includes administration of a β-AR agonist and a peripherally acting β-blocker (PABRA) to a subject in need thereof.

  公开号：

  WO2024137478A1
• 作为产物：
  描述：

  2-溴-2'-氯苯乙酮 在 [RhCl2(p-cymene)]2 、 (R,R,R)-N-camphorsulfonyl-diphenylethylene diamine 、 sodium formate 、 sodium dodecyl-sulfate 作用下， 以 水 为溶剂， 反应 10.0h， 以91%的产率得到(S)-2-溴-1-(2-氯苯基)乙烷-1-醇
  参考文献：
  名称：

  The Ru-catalyzed enantioselective preparation of chiral halohydrins and their application in the synthesis of (R)-clorprenaline and (S)-sotalol

  摘要：

  The asymmetric transfer hydrogenation of a series of halo-substituted aryl methyl ketones, including those substituted in both alpha-methyl and aryl rings, was studied for the preparation of chiral halohydrins. Up to 99.7% ee was obtained with 2-chloro-1-(2-chlorophenyl)ethanone as the substrate and Ru-CsDPEN as the catalyst in an HCOONa/H2O system. (R)-Clorprenaline, a drug used in the treatment of respiratory disorders, such as bronchitis and asthma, and (S)-sotalol, a class-III antiarrhythmic compound, were prepared with these chiral halohydrins. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.04.017

文献信息

• Chiral Guanidine Catalyzed Acylative Kinetic Resolution of Racemic 2-Bromo-1-arylethanols
  作者：Erika Sawada、Kenya Nakata

  DOI：10.1246/cl.200786

  日期：2021.2.5

  In this study, chiral guanidine catalyzed acylative kinetic resolution of racemic 2-bromo-1-arylethanols was achieved with high selectivity. Irrespective of the electronic nature and the substituti...

  在这项研究中，手性胍催化的外消旋 2-溴-1-芳基乙醇的酰化动力学拆分以高选择性实现。不考虑电子性质和替代品...
• 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，