(2S,3S)-4-phenyl-3-bromo-2-butanol | 160189-76-4

• 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: (2S,3S)-4-phenyl-3-bromo-2-butanol
• 英文别名: (-)-(2s,3s)-4-Phenyl-3-bromo-2-butanol；(2S,3S)-3-bromo-4-phenylbutan-2-ol
• CAS: 160189-76-4
• 化学式: C₁₀H₁₃BrO
• 分子量: 229.117
• InChiKey: CYJDFSGKPFBUFY-WPRPVWTQSA-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：

  (2S,3S)-4-phenyl-3-bromo-2-butanol 在 lithium aluminium tetrahydride 、 sodium carbonate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 4.5h， 生成 (S)-(+)-4-苯基-2-丁醇
  参考文献：
  名称：

  On the baker's yeast mediated transformation of α-bromoenones. Synthesis of (1S,2R)-2-bromoindan-1-ol and (2S,3S)-3-bromo-4-phenylbutan-2-ol

  摘要：

  Fermenting baker's yeast converts alpha-bromo substituted enones 7 and 10 into enantiomerically pure (1S,2R)2-bromoindan-1-ol 3 and (2S,3S)-3-bromo-4-phenylbutan-2-ol 11, respectively, through the intermediacy of the corresponding saturated ketones. Structurally related 16 provides the (2R)-allylic alcohol 17 prevalently. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00128-1
• 作为产物：
  描述：

  (Z)-3-bromo-4-phenyl-3-buten-2-one 在 1,3-二硝基苯 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以87%的产率得到(2S,3S)-4-phenyl-3-bromo-2-butanol
  参考文献：
  名称：

  毕赤酵母介导的4-苯基-3-卤代-3-丁烯-2-酮还原中的氢化物转移与电子转移

  摘要：

  毕赤酵母介导的（Z）-C 6 H 5 CHCXC（O）CH 3（X = Cl，Br）的还原通过中间体3-卤代-4-苯基丁烷-2-酮的脱卤作用而得到4-苯基丁酮-2-酮。通过电子转移机制。1,3-二硝基苯的加入避免了脱卤作用，因此通过氢化物转移机理以极好的对映体过量获得了相应的（2 S，3 S）-卤代醇。IRGANOX ® 1010和1076也被用来抑制电子传递机制。所获得的卤代醇是获得旋光性环氧化物和氨基醇的重要手性结构单元。

  DOI：

  10.1016/j.molcatb.2011.07.001

文献信息

• Direct asymmetric bromination of aldehydes catalyzed by a binaphthyl-based secondary amine: highly enantio- and diastereoselective one-pot synthesis of bromohydrins
  作者：Taichi Kano、Fumitaka Shirozu、Keiji Maruoka

  DOI：10.1039/c0cc02739a

  日期：——

  One-pot stereoselective synthesis of bromohydrins as a useful chiral building block was achieved by the reaction of Grignard reagents with optically active alpha-bromoaldehydes, which were in situ generated by direct asymmetric bromination of aldehydes catalyzed by a binaphthyl-based secondary amine (S)-3.

  格氏试剂与旋光性α-溴醛的反应可实现一锅立体选择的溴代醇作为有用的手性结构单元，后者是通过基于双萘基仲胺（S）催化的醛直接不对称溴化而原位生成的-3。
• Chemoenzymatic synthesis of chiral epoxides. Preparation of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane
  作者：Pascale Besse、Michel F. Renard、Henri Veschambre

  DOI：10.1016/0957-4166(94)80167-3

  日期：1994.7

  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.
• 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.
• Hydride transfer versus electron transfer in the reduction of 4-phenyl-3-halo-3-buten-2-ones mediated by Pichia stipitis
  作者：Dávila S. Zampieri、Luiz A. Zampieri、J. Augusto R. Rodrigues、Bruno R.S. de Paula、Paulo J.S. Moran

  DOI：10.1016/j.molcatb.2011.07.001

  日期：2011.11

  Reductions of (Z)-C6H5CHCXC(O)CH3 (X = Cl, Br) mediated by Pichia stipitis gave 4-phenylbutan-2-one through dehalogenation of intermediaries 3-halo-4-phenylbutan-2-one by an electron transfer mechanism. The addition of 1,3-dinitrobenzene avoids the dehalogenation and thus the corresponding (2S,3S)-halohydrins were obtained in excellent enantiomeric excesses by a hydride transfer mechanism. Irganox® 1010 and

  毕赤酵母介导的（Z）-C 6 H 5 CHCXC（O）CH 3（X = Cl，Br）的还原通过中间体3-卤代-4-苯基丁烷-2-酮的脱卤作用而得到4-苯基丁酮-2-酮。通过电子转移机制。1,3-二硝基苯的加入避免了脱卤作用，因此通过氢化物转移机理以极好的对映体过量获得了相应的（2 S，3 S）-卤代醇。IRGANOX ® 1010和1076也被用来抑制电子传递机制。所获得的卤代醇是获得旋光性环氧化物和氨基醇的重要手性结构单元。
• On the baker's yeast mediated transformation of α-bromoenones. Synthesis of (1S,2R)-2-bromoindan-1-ol and (2S,3S)-3-bromo-4-phenylbutan-2-ol
  作者：Josephina Aleu、Giovanni Fronza、Claudio Fuganti、Valentina Perozzo、Stefano Serra

  DOI：10.1016/s0957-4166(98)00128-1

  日期：1998.5

  Fermenting baker's yeast converts alpha-bromo substituted enones 7 and 10 into enantiomerically pure (1S,2R)2-bromoindan-1-ol 3 and (2S,3S)-3-bromo-4-phenylbutan-2-ol 11, respectively, through the intermediacy of the corresponding saturated ketones. Structurally related 16 provides the (2R)-allylic alcohol 17 prevalently. (C) 1998 Elsevier Science Ltd. All rights reserved.