(Z)-2-bromo-1-(dimethyl)phenylsilyl-5-phenyl-2-pentene | 683773-79-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (Z)-2-bromo-1-(dimethyl)phenylsilyl-5-phenyl-2-pentene
• 英文别名: [(Z)-2-bromo-5-phenylpent-2-enyl]-dimethyl-phenylsilane
• CAS: 683773-79-7
• 化学式: C₁₉H₂₃BrSi
• 分子量: 359.381
• InChiKey: GGWLFGAVAXUTHY-AQTBWJFISA-N

物化性质

• 沸点：
  432.7±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  magnesium,methanidyl-dimethyl-propan-2-yloxysilane,chloride 、 (Z)-2-bromo-1-(dimethyl)phenylsilyl-5-phenyl-2-pentene 在 palladium diacetate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.0h， 生成 (E)-1-(dimethyl)isopropoxysilyl-2-[(dimethyl)phenylsilyl]methyl-5-phenyl-2-pentene 、 (Z)-1-(dimethyl)isopropoxysilyl-2-[(dimethyl)phenylsilyl]methyl-5-phenyl-2-pentene
  参考文献：
  名称：

  Synthesis and Reaction of Bromoallylsilane: A Short Access to β,γ-Disubstituted α-Methylene-γ-butyrolactone

  摘要：

  (Z)-beta-Bromoallylsilanes (1a-c) were prepared by a stereoselective Ni-catalyzed cross-coupling reaction of 1,1-dibromo-4-phenylbutene (4) with silylmethylmagnesium halide. Sakurai-Hosomi reaction of la with aldehyde gave syn-3-alkyl-2-bromo-4-hydroxyalkene (2a, 2c, and 2c) and that with acetal gave syn-4-alkoxy-3-alkyl-2-bromoalkene (2b and 2d) stereoselectively. The products with formyl function reacted with a Ni-carbonyl complex to give beta,gamma-disubstituted (alpha-methylene-gamma-butyrolactones (3) in good yields. Pd-catalyzed cross-coupling reaction of la-c or 4 with silylmethylmagnesium halide gave 1, 1-bis(silylmethyl)-1-alkenes (1d-i), which reacted with dimethyl acetal to generate more functionalized allylsilane (6).

  DOI：

  10.3987/com-03-s52
• 作为产物：
  描述：

  magnesium,methanidyl-dimethyl-phenylsilane,chloride 、 4-phenyl-1,1-dibromo-1-butene 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以 乙醚 为溶剂， 以83%的产率得到(Z)-2-bromo-1-(dimethyl)phenylsilyl-5-phenyl-2-pentene
  参考文献：
  名称：

  Synthesis and Reaction of Bromoallylsilane: A Short Access to β,γ-Disubstituted α-Methylene-γ-butyrolactone

  摘要：

  (Z)-beta-Bromoallylsilanes (1a-c) were prepared by a stereoselective Ni-catalyzed cross-coupling reaction of 1,1-dibromo-4-phenylbutene (4) with silylmethylmagnesium halide. Sakurai-Hosomi reaction of la with aldehyde gave syn-3-alkyl-2-bromo-4-hydroxyalkene (2a, 2c, and 2c) and that with acetal gave syn-4-alkoxy-3-alkyl-2-bromoalkene (2b and 2d) stereoselectively. The products with formyl function reacted with a Ni-carbonyl complex to give beta,gamma-disubstituted (alpha-methylene-gamma-butyrolactones (3) in good yields. Pd-catalyzed cross-coupling reaction of la-c or 4 with silylmethylmagnesium halide gave 1, 1-bis(silylmethyl)-1-alkenes (1d-i), which reacted with dimethyl acetal to generate more functionalized allylsilane (6).

  DOI：

  10.3987/com-03-s52