(+/-)-(Z)-2-(6-(dimethylphenylsilyl)-5-(tributylstannyl)-5-hexenyloxy)tetrahydro-2H-pyran | 738591-68-9

• 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-(6-(dimethylphenylsilyl)-5-(tributylstannyl)-5-hexenyloxy)tetrahydro-2H-pyran
• 英文别名: dimethyl-[(Z)-6-(oxan-2-yloxy)-2-tributylstannylhex-1-enyl]-phenylsilane
• CAS: 738591-68-9
• 化学式: C₃₁H₅₆O₂SiSn
• 分子量: 607.58
• InChiKey: ZALSFXCFQSCEGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.17
• 重原子数：
  35.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran 、 dimethylphenyl(tributylstannyl)silane 在 四(三苯基膦)钯 、 乙醚 、 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 作用下， 以 further solvent(s) 为溶剂， 以83%的产率得到(+/-)-(Z)-2-(6-(dimethylphenylsilyl)-5-(tributylstannyl)-5-hexenyloxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  Recyclable palladium(0)-catalysed silylstannation of terminal alkynes in ionic liquids

  摘要：

  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.

  DOI：

  10.1016/j.molcata.2003.09.032