3-bromo-2-phenylpropan-1-ol | 1394246-28-6

• 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: 3-bromo-2-phenylpropan-1-ol
• 英文别名: (2S)-3-bromo-2-phenylpropan-1-ol
• CAS: 1394246-28-6
• 化学式: C₉H₁₁BrO
• 分子量: 215.09
• InChiKey: BVEUKTUILJEUOJ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-苯基-1,3-丙二醇 在 正丁基锂 、 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-1-((R)-2-(4-fluorophenyl)-2-methylpyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)amino)cyclobut-3-ene-1,2-dione 作用下， 以 四氢呋喃 、 甲基叔丁基醚 为溶剂， 反应 24.25h， 生成 3-bromo-2-phenylpropan-1-ol
  参考文献：
  名称：

  A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Brønsted- and Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings

  摘要：

  DOI：

  10.1021/jacs.1c03992

文献信息

• Haloalkane dehalogenase catalysed desymmetrisation and tandem kinetic resolution for the preparation of chiral haloalcohols
  作者：Alja Westerbeek、Jan G.E. van Leeuwen、Wiktor Szymański、Ben L. Feringa、Dick B. Janssen

  DOI：10.1016/j.tet.2012.06.059

  日期：2012.9

  Six different bacterial haloalkane dehalogenases were recombinantly produced in Escherichia coli, purified, and used to catalyse the conversion of prochiral short-chain dihaloalkanes and a meso dihaloalkane, yielding enantioenriched haloalcohols. A two-reaction one-enzyme process was established in which the desymmetrisation of a dihaloalkane is followed by kinetic resolution of the chiral haloalcohol that is produced in the first step. In case of 1,3-dibromo-2-methylpropane and 1,3-dibromo-2-phenylpropane, an increase of the enantiomeric excess of the respective haloalcohol was observed in time, leading to ee values of >97%, with analytical yields of 24 and 52%, respectively. The results show that haloalkane dehalogenases can be used for the production of highly enantioenriched haloalcohols and that in some cases product enantiopurity can be improved by allowing a two-step one-enzyme tandem reaction. (C) 2012 Elsevier Ltd. All rights reserved.
• A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Brønsted- and Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings
  作者：Daniel A. Strassfeld、Russell F. Algera、Zachary K. Wickens、Eric N. Jacobsen

  DOI：10.1021/jacs.1c03992

  日期：2021.6.30