(-)-(2R,3S)-4-phenyl-3-bromo-2-butanol | 160189-79-7

• 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,3S)-4-phenyl-3-bromo-2-butanol
• 英文别名: (2R,3S)-3-bromo-4-phenyl-2-butanol
• CAS: 160189-79-7
• 化学式: C₁₀H₁₃BrO
• 分子量: 229.117
• InChiKey: CYJDFSGKPFBUFY-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3S)-4-phenyl-3-bromo-2-butanol 在 sodium ethanolate 作用下， 以 甲醇 为溶剂， 生成 trans-1-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：

  苄基丙酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 (Ph)3P⁺CH₂CH₂COOH*Br₃^- 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 (-)-(2R,3S)-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

• 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。