(1S,2R)-2-Bromo-1-phenyl-but-3-en-1-ol

• 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: (1S,2R)-2-Bromo-1-phenyl-but-3-en-1-ol
• 英文别名: (1S,2R)-2-bromo-1-phenylbut-3-en-1-ol
• 化学式: C₁₀H₁₁BrO
• 分子量: 227.101
• InChiKey: ACOXTZWYOWKAJD-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (1S,2R)-2-Bromo-1-phenyl-but-3-en-1-ol 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 反式-2-苯基-3-乙烯基环氧乙烷
  参考文献：
  名称：

  Diastereo- and Enantioselective Synthesis of syn-α-Vinylchlorohydrins and cis-Vinylepoxides

  摘要：

  A new method to generate chiral syn-vinylchlorohydrins and cis-vinyloxiranes is reported. Reaction of (alpha-haloallyl)lithiums with methoxy-9-BBN or Ipc(2)BOMe followed by treatment with BF3 . OEt(2) leads to (Z)-(gamma-haloallyl)boranes which react with aldehydes to yield cis-vinylepoxides (de greater than or equal to 90%) upon oxidative workup. Alternatively, addition of ethanolamine to the allylboration product yields syn-alpha a-halohydrins (de greater than or equal to 90%) that are also easily cyclized to cis-vinylepoxides. Extension of this protocol using [(Z)-gamma-chloroallyl]BIpc(2) leads to chiral syn-alpha-chlorohydrins and cis-vinylepoxides in high de (greater than or equal to 90%) and ee(90-99%). Enantioselectivity of reactions of chiral (Z)-(gamma-chloroallyl)boranes with aldehydes are more sensitive to reaction conditions than enantioselectivity of reactions of other alpha-or gamma-substituted allylboranes. The effects of proportion ofBF(3) . OEt(2) and the relative efficacies of LiNR(2) bases on diastereo- and enantioselectivity of the chloroallylation are reported.

  DOI：

  10.1021/jo960875p
• 作为产物：
  描述：

  [(E)-3-bromoprop-2-enyl]-trichlorosilane 、 苯甲醛 在 N,N-二甲基甲酰胺 作用下， 反应 24.0h， 生成 (1S,2R)-2-Bromo-1-phenyl-but-3-en-1-ol
  参考文献：
  名称：

  Synthesis of γ-functionalized allyltrichlorosilanes and their application in the asymmetric allylation of aldehydes

  摘要：

  Isomerically pure trans- and cis-gamma-bromoallyltrichlorosilanes 4 and 5 have been synthesized and shown to react with aromatic aldehydes 1 in the presence of Lewis-basic catalysts (e.g., DMF) to produce the corresponding anti- and syn-allylbromohydrins 8 and 9, respectively, as single diastereoisomers. With BINAPO 25 as a chiral catalyst, promising enantioselectivity (<= 50% ee) has been attained. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.026

文献信息

• Diastereo- and Enantioselective Synthesis of <i>syn</i>-α-Vinylchlorohydrins and <i>cis</i>-Vinylepoxides
  作者：Shaojing Hu、Seetharaman Jayaraman、Allan C. Oehlschlager

  DOI：10.1021/jo960875p

  日期：1996.1.1

  A new method to generate chiral syn-vinylchlorohydrins and cis-vinyloxiranes is reported. Reaction of (alpha-haloallyl)lithiums with methoxy-9-BBN or Ipc(2)BOMe followed by treatment with BF3 . OEt(2) leads to (Z)-(gamma-haloallyl)boranes which react with aldehydes to yield cis-vinylepoxides (de greater than or equal to 90%) upon oxidative workup. Alternatively, addition of ethanolamine to the allylboration product yields syn-alpha a-halohydrins (de greater than or equal to 90%) that are also easily cyclized to cis-vinylepoxides. Extension of this protocol using [(Z)-gamma-chloroallyl]BIpc(2) leads to chiral syn-alpha-chlorohydrins and cis-vinylepoxides in high de (greater than or equal to 90%) and ee(90-99%). Enantioselectivity of reactions of chiral (Z)-(gamma-chloroallyl)boranes with aldehydes are more sensitive to reaction conditions than enantioselectivity of reactions of other alpha-or gamma-substituted allylboranes. The effects of proportion ofBF(3) . OEt(2) and the relative efficacies of LiNR(2) bases on diastereo- and enantioselectivity of the chloroallylation are reported.
• Synthesis of γ-functionalized allyltrichlorosilanes and their application in the asymmetric allylation of aldehydes
  作者：Andrei V. Malkov、Claire MacDonald、Pavel Kočovský

  DOI：10.1016/j.tetasy.2010.03.026

  日期：2010.5

  Isomerically pure trans- and cis-gamma-bromoallyltrichlorosilanes 4 and 5 have been synthesized and shown to react with aromatic aldehydes 1 in the presence of Lewis-basic catalysts (e.g., DMF) to produce the corresponding anti- and syn-allylbromohydrins 8 and 9, respectively, as single diastereoisomers. With BINAPO 25 as a chiral catalyst, promising enantioselectivity (<= 50% ee) has been attained. (C) 2010 Elsevier Ltd. All rights reserved.