(+)-(2R,3R)-4-phenyl-3-bromo-2-butanol | 160189-78-6

• 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: (+)-(2R,3R)-4-phenyl-3-bromo-2-butanol
• 英文别名: (2R,3R)-3-bromo-4-phenylbutan-2-ol
• CAS: 160189-78-6
• 化学式: C₁₀H₁₃BrO
• 分子量: 229.117
• InChiKey: CYJDFSGKPFBUFY-PSASIEDQSA-N

物化性质

• 沸点：
  296.8±20.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (+)-(2R,3R)-4-phenyl-3-bromo-2-butanol 在 sodium ethanolate 作用下， 以 甲醇 为溶剂， 以87%的产率得到(+)-(2R,3S)-4-phenyl-2,3-epoxybutane
  参考文献：
  名称：

  Chemoenzymatic synthesis of chiral epoxides. Preparation of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane

  摘要：

  All the stereoisomers of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane (beta-methylstyrene oxide) have been prepared in three steps from 4-phenyl-2-butanone and 1-phenyl-2-propanone or 1-phenyl-1-propanone respectively. The key step is the microbiological reduction of the corresponding haloketones. These results confirm those previously described(1) and demonstrate that the chemoenzymatic synthesis of homochiral 2,3-epoxides is a general method that can be used whatever the starting ketone.

  DOI：

  10.1016/0957-4166(94)80167-3
• 作为产物：
  描述：

  3-溴-4-苯基-2-丁酮 反应 24.0h， 以48%的产率得到(+)-(2R,3R)-4-phenyl-3-bromo-2-butanol
  参考文献：
  名称：

  Chemoenzymatic synthesis of chiral epoxides. Preparation of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane

  摘要：

  All the stereoisomers of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane (beta-methylstyrene oxide) have been prepared in three steps from 4-phenyl-2-butanone and 1-phenyl-2-propanone or 1-phenyl-1-propanone respectively. The key step is the microbiological reduction of the corresponding haloketones. These results confirm those previously described(1) and demonstrate that the chemoenzymatic synthesis of homochiral 2,3-epoxides is a general method that can be used whatever the starting ketone.

  DOI：

  10.1016/0957-4166(94)80167-3

文献信息

• Enhancements of enantio and diastereoselectivities in reduction of (Z)-3-halo-4-phenyl-3-buten-2-one mediated by microorganisms in ionic liquid/water biphasic system
  作者：Dávila S. Zampieri、Bruno R.S. de Paula、Luiz A. Zampieri、Juliana A. Vale、J. Augusto R. Rodrigues、Paulo J.S. Moran

  DOI：10.1016/j.molcatb.2012.08.005

  日期：2013.1

  Reductions of (Z)-C6H5CH=CXC(=O)CH3 (X=Cl, Br) mediated by Saccharomyces cerevisiae, Candida albicans, Rhodotorula glutinis, Geotrichum candidum and Micrococcus luteus gave the corresponding halohydrins through consecutive reduction reactions of C=C and C=O bonds. In general, the reactions performed in the biphasic system water/[(bmim)PF6] gave better diastereoselectivity and enantioselectivity than in pure water. (C) 2012 Elsevier B.V. All rights reserved.