(Z)-5-(tributylstannyl)-6-(trimethylsilyl)hex-5-en-1-ol | 489470-67-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: (Z)-5-(tributylstannyl)-6-(trimethylsilyl)hex-5-en-1-ol
• CAS: 489470-67-9
• 化学式: C₂₁H₄₆OSiSn
• 分子量: 461.391
• InChiKey: ZOUMDMVYDBNIIO-UHFFFAOYSA-N

物化性质

• 沸点：
  441.7±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.34
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-己炔-1-醇 、 叔丁基锡烷 在 四(三苯基膦)钯 作用下， 以 乙醚 为溶剂， 以89%的产率得到(Z)-5-(tributylstannyl)-6-(trimethylsilyl)hex-5-en-1-ol
  参考文献：
  名称：

  Silylstannation of terminal alkynes using a recyclable palladium(0) catalyst immobilised in an ionic liquid

  摘要：

  硅烷锡化合物可以在含有固定化的钯(0)催化剂的[bmim]PF6离子液体中以定向选择性方式定量地加成于末端炔烃，并且催化剂可以循环使用而不失活。

  DOI：

  10.1039/b205999a

文献信息

• Recyclable palladium(0)-catalysed silylstannation of terminal alkynes in ionic liquids
  作者：I Hemeon

  DOI：10.1016/j.molcata.2003.09.032

  日期：2004.5.18

  The palladium(0)-catalysed addition of silylstannanes Bu3SnSiMe3 and Bu3SnSiMe2Ph to terminal alkynes has been shown to proceed in the ionic liquids 1-n-butyl-3-methylimidazolium hexafluorophosphate ([bmim]PF6) and 1-n-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4). These reactions generally proceed in excellent yields to give 1-trialkylsilyl-2-tributylstannyl-1Z-alkenes regio- and stereoselectively as a single product with reaction times comparable to those reported for reactions performed in tetrahydrofuran (THF). The reaction has been shown to tolerate remote functionality on the alkyne. Each of the ionic liquids containing the immobilised palladium catalyst has been recycled up to 10 times without loss of activity, allowing extensive reuse of the expensive solvent/catalyst system. A catalyst activation stage involving mild heating of the palladium catalyst in the ionic liquid/diethyl ether solvent system decreased reaction time in the first cycle once all reagents were added, indicating the formation of a catalytically active palladium species other than tetrakis(triphenylphosphine)palladium(0). (C) 2004 Elsevier B.V. All rights reserved.
• Silylstannation of terminal alkynes using a recyclable palladium(0) catalyst immobilised in an ionic liquid
  作者：Ivan Hemeon、Robert D. Singer

  DOI：10.1039/b205999a

  日期：2002.8.21

  Silylstannanes can be regioselectively added across terminal alkynes in a quantitative fashion in the presence of a palladium(0) catalyst immobilised in the [bmim]PF6 ionic liquid which can be recycled without loss of activity.

  硅烷锡化合物可以在含有固定化的钯(0)催化剂的[bmim]PF6离子液体中以定向选择性方式定量地加成于末端炔烃，并且催化剂可以循环使用而不失活。