(Z)-2-(dimethylphenylsilyl)-1-phenyl-1-(tributylstannyl)ethene | 213317-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-2-(dimethylphenylsilyl)-1-phenyl-1-(tributylstannyl)ethene
• 英文别名: (Z)-dimethyl(phenyl)(2-phenyl-2-(tributylstannyl)vinyl)silane；dimethyl-phenyl-[(Z)-2-phenyl-2-tributylstannylethenyl]silane
• CAS: 213317-85-2；122229-70-3
• 化学式: C₂₈H₄₄SiSn
• 分子量: 527.453
• InChiKey: SCBQHFJBEKKZOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.03
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  (Z)-2-(dimethylphenylsilyl)-1-phenyl-1-(tributylstannyl)ethene 在 正丁基锂 、 水 作用下， 生成 dimethyl(phenyl)(2-phenylethenyl)silane
  参考文献：
  名称：

  钯（0）催化的具有Si-Se，Ge-Se和Si-Ge键的杂原子化合物的区域和立体选择性加成到苯乙炔

  摘要：

  新颖的钯（0）催化的硒化甲硅烷基（1，Me 3 SiSePh）加到苯乙炔中的区域和立体选择性生成（Z）-1-苯基硒基2（三甲基甲硅烷基）苯乙烯（2）。同样，胚芽硒化物（3，Me 3 GeSePh）以优异的区域选择性和立体选择性加到苯乙炔中。

  DOI：

  10.1016/s0022-328x(97)00514-7
• 作为产物：
  描述：

  dimethylphenyl(tributylstannyl)silane 、 苯乙炔 在 四(三苯基膦)钯 、 乙醚 、 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 以 further solvent(s) 为溶剂， 以97%的产率得到(Z)-2-(dimethylphenylsilyl)-1-phenyl-1-(tributylstannyl)ethene
  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

文献信息

• Inverse regioselectivity in the silylstannylation of alkynes and allenes: copper-catalyzed three-component coupling with a silylborane and a tin alkoxide
  作者：H. Yoshida、Y. Hayashi、Y. Ito、K. Takaki

  DOI：10.1039/c5cc01856k

  日期：——

  Silylstannylation of alkynes and allenes has been found to proceed by three-component coupling using a silylborane and a tin alkoxide in the presence of a Cu(I) catalyst. The regioselectivities are...

  已经发现在Cu（I）催化剂存在下，使用甲硅烷基硼烷和锡醇盐通过三组分偶联进行炔烃和丙二烯的甲硅烷基锡烷基化反应。区域选择性是...
• RITTER, KURT, SYNTHESIS (BRD),(1989) N, C. 218-221
  作者：RITTER, KURT

  DOI：——

  日期：——
• Palladium(0)-catalyzed regio- and stereoselective addition of heteroatom compounds bearing Si–Se, Ge–Se, and Si–Ge bonds to phenylacetylene
  作者：Akiya Ogawa、Hitoshi Kuniyasu、Mitsuhiro Takeba、Takuma Ikeda、Noboru Sonoda、Toshikazu Hirao

  DOI：10.1016/s0022-328x(97)00514-7

  日期：1998.8

  A novel palladium(0)-catalyzed addition of a silyl selenide (1, Me3SiSePh) to phenylacetylene proceeds regio- and stereoselectively to give (Z)-1-phenylseleno-2(trimethylsilyl)styrene (2). Similarly, a germyl selenide (3, Me3GeSePh) adds to phenylacetylene with excellent regio- and stereoselectivity.

  新颖的钯（0）催化的硒化甲硅烷基（1，Me 3 SiSePh）加到苯乙炔中的区域和立体选择性生成（Z）-1-苯基硒基2（三甲基甲硅烷基）苯乙烯（2）。同样，胚芽硒化物（3，Me 3 GeSePh）以优异的区域选择性和立体选择性加到苯乙炔中。
• 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.