(Z)-4-(Tributylstannyl)-4-(trimethylsilyl)but-3-en-2-ol | 138154-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-4-(Tributylstannyl)-4-(trimethylsilyl)but-3-en-2-ol
• CAS: 138154-03-7
• 化学式: C₁₉H₄₂OSiSn
• 分子量: 433.337
• InChiKey: KOLHARCRKBZPQE-UHFFFAOYSA-N

物化性质

• 沸点：
  418.1±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 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：

  (Z)-4-(Tributylstannyl)-4-(trimethylsilyl)but-3-en-2-ol 在 Rh(norbornadiene)(bis(diphenylphosphino)butane)(+)BF4(-) 氢气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， -78.0 ℃ 、10.34 MPa 条件下， 反应 26.5h， 生成 (2R*,4S*)-4-(Triisopropylsilyl)-4-(trimethylsilyl)butan-2-ol
  参考文献：
  名称：

  Exploring the reactivity of alkenes bearing silicon and/or tin in the hydroxyl-directed hydrogenation. A diastereoselective synthesis of heterobimetallic compounds

  摘要：

  The hydroxyl-directed hydrogenation of (E)- and (Z)-gamma-hydroxy vinylstannanes and silanes has been studied in the presence of (dppb)Rh(NBD)BF4 (1). Efficient routes to gamma-hydroxy stannanes and silanes have been developed. Diastereoselectivities from 60 to >500:1 were observed. A significant difference in reaction rate and pathway was observed between the (E)- and (Z)-vinylstannanes. We observed a reductive destannation process for the (Z)-stannanes which was influenced by the size of the R group. Competition studies were carried out to determine if steric or electronic effects were responsible for the reactivity patterns observed.

  DOI：

  10.1021/jo00100a023
• 作为产物：
  描述：

  (Z)-4-(Tributylstannyl)-4-(trimethylsilyl)but-3-en-2-ol trimethylsilyl ether 在 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以37%的产率得到(Z)-4-(Tributylstannyl)-4-(trimethylsilyl)but-3-en-2-ol
  参考文献：
  名称：

  Exploring the reactivity of alkenes bearing silicon and/or tin in the hydroxyl-directed hydrogenation. A diastereoselective synthesis of heterobimetallic compounds

  摘要：

  The hydroxyl-directed hydrogenation of (E)- and (Z)-gamma-hydroxy vinylstannanes and silanes has been studied in the presence of (dppb)Rh(NBD)BF4 (1). Efficient routes to gamma-hydroxy stannanes and silanes have been developed. Diastereoselectivities from 60 to >500:1 were observed. A significant difference in reaction rate and pathway was observed between the (E)- and (Z)-vinylstannanes. We observed a reductive destannation process for the (Z)-stannanes which was influenced by the size of the R group. Competition studies were carried out to determine if steric or electronic effects were responsible for the reactivity patterns observed.

  DOI：

  10.1021/jo00100a023