(Z)-(1-bromo-2-fluoro-3,3-dimethylbut-1-enyl)benzene | 1112153-79-3

• 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)-(1-bromo-2-fluoro-3,3-dimethylbut-1-enyl)benzene
• 英文别名: [(Z)-1-bromo-2-fluoro-3,3-dimethylbut-1-enyl]benzene
• CAS: 1112153-79-3
• 化学式: C₁₂H₁₄BrF
• 分子量: 257.146
• InChiKey: RPNGZWDGJUJWEM-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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)-(1-bromo-2-fluoro-3,3-dimethylbut-1-enyl)benzene 在 bis-triphenylphosphine-palladium(II) chloride 、 甲酸 、 三正丁胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以47%的产率得到(E)-(2-fluoro-3,3-dimethylbut-1-enyl)benzene
  参考文献：
  名称：

  Stereocontrolled Approach to Bromofluoroalkenes and Their Use for the Synthesis of Tri- and Tetrasubstituted Fluoroalkenes

  摘要：

  An addition/elimination reaction of organolithium reagents to silylated beta,beta-difluorostyrene derivatives followed by a bromination/desilicobromination reaction provides a simple and effective synthetic approach to a wide range of bromofluoroalkenes (up to >97/3). In addition, the bromofluoroalkenes can be used in Pd-catalyzed transformations giving access to both tri- and tetrasubstituted fluoroalkenes.

  DOI：

  10.1021/ol8027412
• 作为产物：
  描述：

  ((E)-2-fluoro-3,3-dimethyl-1-phenylbut-1-enyl)trimethylsilane 在 溴 、 sodium methylate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 生成 (Z)-(1-bromo-2-fluoro-3,3-dimethylbut-1-enyl)benzene 、 (E)-(1-bromo-2-fluoro-3,3-dimethylbut-1-enyl)benzene
  参考文献：
  名称：

  Stereocontrolled Approach to Bromofluoroalkenes and Their Use for the Synthesis of Tri- and Tetrasubstituted Fluoroalkenes

  摘要：

  An addition/elimination reaction of organolithium reagents to silylated beta,beta-difluorostyrene derivatives followed by a bromination/desilicobromination reaction provides a simple and effective synthetic approach to a wide range of bromofluoroalkenes (up to >97/3). In addition, the bromofluoroalkenes can be used in Pd-catalyzed transformations giving access to both tri- and tetrasubstituted fluoroalkenes.

  DOI：

  10.1021/ol8027412

文献信息

• Stereocontrolled Approach to Bromofluoroalkenes and Their Use for the Synthesis of Tri- and Tetrasubstituted Fluoroalkenes
  作者：Grégory Landelle、Pier Alexandre Champagne、Xavier Barbeau、Jean-François Paquin

  DOI：10.1021/ol8027412

  日期：2009.2.5

  An addition/elimination reaction of organolithium reagents to silylated beta,beta-difluorostyrene derivatives followed by a bromination/desilicobromination reaction provides a simple and effective synthetic approach to a wide range of bromofluoroalkenes (up to >97/3). In addition, the bromofluoroalkenes can be used in Pd-catalyzed transformations giving access to both tri- and tetrasubstituted fluoroalkenes.