(+)-(2S,3R)-4-phenyl-3-bromo-2-butanol | 160189-77-5

• 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: (+)-(2S,3R)-4-phenyl-3-bromo-2-butanol
• 英文别名: (2S,3R)-3-bromo-4-phenyl-2-butanol；(2S,3R)-3-bromo-4-phenylbutan-2-ol
• CAS: 160189-77-5
• 化学式: C₁₀H₁₃BrO
• 分子量: 229.117
• InChiKey: CYJDFSGKPFBUFY-WCBMZHEXSA-N

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,3R)-4-phenyl-3-bromo-2-butanol 在 sodium ethanolate 作用下， 以 甲醇 为溶剂， 以90%的产率得到(-)-(2S,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， 生成 (2S,3S)-4-phenyl-3-bromo-2-butanol 、 (+)-(2S,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

• Molecular design of thermostable alcohol dehydrogenase for synthesis for chiral aromatic alcohols
  申请人：Zeikus J. Gregory

  公开号：US20080220487A1

  公开（公告）日：2008-09-11

  The present invention relates to compositions and methods utilizing thermostable and novel alcohol dehydrogenase enzymes for biosynthesizing chiral specific molecules for use as precursor molecules in synthesizing pharmaceutical compounds. Particularly, in preferred embodiments, the invention relates to directed engineering of an enzymatic catalytic site of an alcohol dehydrogenase enzyme gene for enhancing enantioselectivity for (S)-enantiomer substrate catalytic activity for providing aryl (S)-enantiomer products in stereomeric excess.

  本发明涉及利用耐热和新型醇脱氢酶酶的组合物和方法，用于生物合成手性特异分子，作为合成药物化合物的前体分子。特别地，在优选实施例中，本发明涉及对醇脱氢酶酶基因的酶催化位点进行定向工程，以增强对(S)-对映体底物的对映选择性催化活性，从而提供(S)-对映体产物的立体过量。
• 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。
• US7750135B2
  申请人：——

  公开号：US7750135B2

  公开（公告）日：2010-07-06
• 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.