(S)-2-bromo-1-(3,4-dichloro-phenyl)ethanol | 390405-95-5

• 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: (S)-2-bromo-1-(3,4-dichloro-phenyl)ethanol
• 英文别名: (S)-2-bromo-1-(3,4-dichlorophenyl)ethanol；(1S)-2-bromo-1-(3,4-dichlorophenyl)ethanol
• CAS: 390405-95-5
• 化学式: C₈H₇BrCl₂O
• 分子量: 269.953
• InChiKey: ZFMARCNWWLHGAZ-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 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：

  (S)-2-bromo-1-(3,4-dichloro-phenyl)ethanol 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 19.5h， 生成 (S)-Dichloroisoproterenol
  参考文献：
  名称：

  β-肾上腺素能阻滞剂的不对称合成涉及原位手性有机催化剂形成的多步一锅法转化

  摘要：

  两只鸟一块石头：公开了一种用于对映选择性手性药物合成的新的原子经济单罐方法，该方法涉及原位多步有机催化剂的形成以及该反应在β-肾上腺素能阻滞剂多步序贯合成中的应用（参见方案）。

  DOI：

  10.1002/chem.201102931
• 作为产物：
  描述：

  2-溴-3',4'-二氯苯乙酮 在 sodium acetate 作用下， 以 水 为溶剂， 反应 2.0h， 以93%的产率得到(S)-2-bromo-1-(3,4-dichloro-phenyl)ethanol
  参考文献：
  名称：

  咪唑修饰的手性铑/二胺官能化的周期性介孔有机硅用于水介质中[小α]-卤代酮和苯的不对称转移加氢

  摘要：

  非常需要使用疏水的，咪唑鎓官能化的周期性介孔有机二氧化硅作为非均相催化剂来固定手性有机金属配合物，因为该催化剂可以大大促进水性...

  DOI：

  10.1039/c6gc01589a

文献信息

• Synthesis of optically active α-bromohydrins via reduction of α-bromoacetophenone analogues catalyzed by an isolated carbonyl reductase
  作者：Jie Ren、Wenyue Dong、Benqing Yu、Qiaqing Wu、Dunming Zhu

  DOI：10.1016/j.tetasy.2012.03.015

  日期：2012.4

  Enantiomerically pure (S)-alpha-bromohydrins were prepared by the reduction of alpha-bromoacetophenone analogues catalyzed by an isolated carbonyl reductase from Candida magnolia with high yield and excellent enantiomeric excess when methyl tert-butyl ether was employed as the co-solvent, while avoiding the formation of by-products. This provides a new approach to access these chiral alpha-bromohydrins which are of pharmaceutical importance. (C) 2012 Elsevier Ltd. All rights reserved.
• Discovery and initial structure–Activity relationships of trisubstituted ureas as thrombin receptor (PAR-1) antagonists
  作者：James C Barrow、Philippe G Nantermet、Harold G Selnick、Kristen L Glass、Phung L Ngo、Mary Beth Young、Janetta M Pellicore、Michael J Breslin、John H Hutchinson、Roger M Freidinger、Cindra Condra、Jerzy Karczewski、Rodney A Bednar、Stanley L Gaul、Andrew Stern、Robert Gould、Thomas M Connolly

  DOI：10.1016/s0960-894x(01)00538-8

  日期：2001.10

  Thrombin is the most potent agonist of platelet activation, and its effects are predominantly mediated by platelet thrombin receptors. Therefore, antagonists of the thrombin receptor have potential utility for the treatment of thrombotic disorders. Screening of combinatorial libraries revealed 2 to be a potent antagonist of the thrombin receptor. Modifications of this structure produced 11k, which inhibits thrombin receptor stimulated secretion and aggregation of platelets. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Asymmetric Synthesis of β-Adrenergic Blockers through Multistep One-Pot Transformations Involving In Situ Chiral Organocatalyst Formation
  作者：Shengwei Wei、Regina Messerer、Svetlana B. Tsogoeva

  DOI：10.1002/chem.201102931

  日期：2011.12.16

  Two birds one stone: A new atom‐economical one‐pot approach to enantioselective chiral drug synthesis, involving in situ multistep organocatalyst formation and the application of the reaction for multistep sequential synthesis of β‐adrenergic blockers is disclosed (see scheme).

  两只鸟一块石头：公开了一种用于对映选择性手性药物合成的新的原子经济单罐方法，该方法涉及原位多步有机催化剂的形成以及该反应在β-肾上腺素能阻滞剂多步序贯合成中的应用（参见方案）。
• An imidazolium-modified chiral rhodium/diamine-functionalized periodic mesoporous organosilica for asymmetric transfer hydrogenation of α-haloketones and benzils in aqueous medium
  作者：Feng Zhou、Xiaoying Hu、Ming Gao、Tanyu Cheng、Guohua Liu

  DOI：10.1039/c6gc01589a

  日期：——

  Use of a hydrophobic, imidazolium-functionalized periodic mesoporous organosilica for immobilizations of chiral organometallic complexes as a heterogeneous catalyst is a highly desirable as this catalyst can promote greatly an aqueous...

  非常需要使用疏水的，咪唑鎓官能化的周期性介孔有机二氧化硅作为非均相催化剂来固定手性有机金属配合物，因为该催化剂可以大大促进水性...