(Z)-2,3-dimethyl-1-(dimethyl(phenyl)silyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-butene | 206769-46-2

• 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)-2,3-dimethyl-1-(dimethyl(phenyl)silyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-butene
• 英文别名: [(Z)-2,3-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-enyl]-dimethyl-phenylsilane
• CAS: 206769-46-2
• 化学式: C₂₀H₃₃BO₂Si
• 分子量: 344.377
• InChiKey: JYTLZDJMKDCZHS-MSUUIHNZSA-N

物化性质

• 沸点：
  402.7±45.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-2,3-dimethyl-1-(dimethyl(phenyl)silyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-butene 、 苯甲醛 在 三乙醇胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以87%的产率得到(1RS,2RS)-2,3-dimethyl-2-((dimethyl(phenyl)silyl)methyl)-1-phenyl-3-buten-1-ol
  参考文献：
  名称：

  Stereoselective 1,4-Silaboration of 1,3-Dienes Catalyzed by Nickel Complexes

  摘要：

  The silicon-boron bond of (dimethylphenylsilyl)pinacolborane was stereoselectively added to acyclic 1,3-dienes in a 1,4-fashion to give (Z)4-boryl-1 -silyl-2-alkene derivatives in the presence of a Ni(0) catalyst generated from Ni(acac)(2) and diisobutylaluminum hydride, 1,4-Silaboration of cyclic 1,3-dienes required the use of cyclohexyldiphenylphosphine with the Ni(0) catalyst to afford cis-1-boryl-1-silyl-2-cycloalkene derivatives in high yields with high stereoselectivities.

  DOI：

  10.1021/ol990908y
• 作为产物：
  描述：

  2,3-二甲基-1,3-丁二烯 、 (二甲基苯硅烷基)硼酸频那醇酯 在 bis(acetylacetonate)nickel(II) 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以90%的产率得到(Z)-2,3-dimethyl-1-(dimethyl(phenyl)silyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-butene
  参考文献：
  名称：

  Stereoselective 1,4-Silaboration of 1,3-Dienes Catalyzed by Nickel Complexes

  摘要：

  The silicon-boron bond of (dimethylphenylsilyl)pinacolborane was stereoselectively added to acyclic 1,3-dienes in a 1,4-fashion to give (Z)4-boryl-1 -silyl-2-alkene derivatives in the presence of a Ni(0) catalyst generated from Ni(acac)(2) and diisobutylaluminum hydride, 1,4-Silaboration of cyclic 1,3-dienes required the use of cyclohexyldiphenylphosphine with the Ni(0) catalyst to afford cis-1-boryl-1-silyl-2-cycloalkene derivatives in high yields with high stereoselectivities.

  DOI：

  10.1021/ol990908y

文献信息

• Stereoselective 1,4-Silaboration of 1,3-Dienes Catalyzed by Nickel Complexes
  作者：Michinori Suginome、Takanori Matsuda、Takayo Yoshimoto、Yoshihiko Ito

  DOI：10.1021/ol990908y

  日期：1999.11.1

  The silicon-boron bond of (dimethylphenylsilyl)pinacolborane was stereoselectively added to acyclic 1,3-dienes in a 1,4-fashion to give (Z)4-boryl-1 -silyl-2-alkene derivatives in the presence of a Ni(0) catalyst generated from Ni(acac)(2) and diisobutylaluminum hydride, 1,4-Silaboration of cyclic 1,3-dienes required the use of cyclohexyldiphenylphosphine with the Ni(0) catalyst to afford cis-1-boryl-1-silyl-2-cycloalkene derivatives in high yields with high stereoselectivities.