(Z)-(5-Bromo-4-fluoropent-3-enyl)benzene | 1582802-63-8

• 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: (Z)-(5-Bromo-4-fluoropent-3-enyl)benzene
• 英文别名: [(Z)-5-bromo-4-fluoropent-3-enyl]benzene
• CAS: 1582802-63-8
• 化学式: C₁₁H₁₂BrF
• 分子量: 243.119
• InChiKey: OBQPCGQJFZZWEY-FLIBITNWSA-N

物化性质

• 沸点：
  292.9±40.0 °C(predicted)
• 密度：
  1.322±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-(5-Bromo-4-fluoropent-3-enyl)benzene 、 丁烯-2-醛 在 indium 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 (E)-2-fluoro-3-phenethylhepta-1,5-dien-4-ol 、 (E)-2-fluoro-3-phenethylhepta-1,5-dien-4-ol
  参考文献：
  名称：

  Efficient access to fluorinated homoallylic alcohols through an indium promoted fluoroallylation reaction

  摘要：

  Herein, an efficient access to fluorinated homoallylic alcohol is reported. The fluorinated alcohols were obtained in good to excellent yield using indium and halo-fluorinated allylic derivatives. The developed methodology using gamma-substituted halo-fluorinated allylic derivatives gave the corresponding alpha-substituted fluorinated homoallylic alcohol in good yields and good diastereoselectivities up to 86:14. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.067
• 作为产物：
  描述：

  (Z)-5-phenyl-2-fluoropent-2-en-1-ol 在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以50%的产率得到(Z)-(5-Bromo-4-fluoropent-3-enyl)benzene
  参考文献：
  名称：

  Efficient access to fluorinated homoallylic alcohols through an indium promoted fluoroallylation reaction

  摘要：

  Herein, an efficient access to fluorinated homoallylic alcohol is reported. The fluorinated alcohols were obtained in good to excellent yield using indium and halo-fluorinated allylic derivatives. The developed methodology using gamma-substituted halo-fluorinated allylic derivatives gave the corresponding alpha-substituted fluorinated homoallylic alcohol in good yields and good diastereoselectivities up to 86:14. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.067

文献信息

• Indium-Promoted Diastereoselective Addition of Fluorinated Haloallylic Derivatives to Imines
  作者：Gérald Lemonnier、Nathalie Van Hijfte、Thomas Poisson、Samuel Couve-Bonnaire、Xavier Pannecoucke

  DOI：10.1021/jo402810s

  日期：2014.4.4

  We report herein the first general access to fluorinated homoallylic amines by means of an addition of fluorinated organoindium reagent. The corresponding amines were obtained in good to excellent yield with excellent diastereoisomeric ratio. A plausible mechanism is proposed to explain the stereochemical outcome of the reaction based on the X-ray structure of the products.

  我们在此报告了通过添加氟化有机铟试剂而首次获得氟化均烯丙基胺。以良好至优异的产率和优异的非对映异构体比率获得相应的胺。根据产物的X射线结构，提出了一种合理的机理来解释反应的立体化学结果。