triethylsilyl tri-n-butylstannane | 646536-78-9

• 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: triethylsilyl tri-n-butylstannane
• CAS: 646536-78-9
• 化学式: C₁₈H₄₂SiSn
• 分子量: 405.327
• InChiKey: IVYZWWHWUSZBGB-UHFFFAOYSA-N

物化性质

• 沸点：
  366.2±11.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.42
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  triethylsilyl tri-n-butylstannane 、 2-naphthyl pivalate 在 bis(1,5-cyclooctadiene)nickel (0) 、 cesium fluoride 、 1,2-双(二环己基磷基)-乙烷 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以31%的产率得到tributyl(naphthalene-2-yl)stannane
  参考文献：
  名称：

  Ni通过C-O键裂解催化芳基酯的甲氧基化

  摘要：

  描述了一种通过空气 裂解对水和不敏感的甲硅烷基锡烷基转移试剂进行镍催化的芳基酯的锡烷基化反应。该协议的特点是适用范围广，包括具有挑战性的组合，因此可以访问通用的构建基块和正交的C-杂原子键形成。

  DOI：

  10.1002/anie.201611720
• 作为产物：
  描述：

  三乙基氯硅烷 、 三正丁基氢锡 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到triethylsilyl tri-n-butylstannane
  参考文献：
  名称：

  Axial Chirality in 1,4-Disubstituted (ZZ)-1,3-Dienes. Surprisingly Low Energies of Activation for the Enantiomerization in Synthetically Useful Fluxional Molecules

  摘要：

  Trialkylsilyltrialkylstannes (R3Si-SnR'(3)) add to 1,6-diynes in the presence of Pd(0) and trispentaflurophenylphosphine to give 1,2-dialkylidenecyclopentanes with terminal silicon and tin substituents. The (ZZ)-geometry of these s-cis-1,3-dienes, resulting from the organometallic reaction mechanisms involved, forces the silicon and tin groups to be nonplanar, thus making the molecules axially chiral. There is rapid equilibration between the two helical forms at room-temperature irrespective of the size of the Si and Sn substituents. However, the two forms can be observed by H-1, C-13, and Sn-119 NMR spectroscopy at low temperature. The rates of enantiomerization, which depend on the Si and Sn substituents, and the substitution pattern of the cylopentane ring can be studied by dynamic NMR spectroscopy using line shape analysis. The surprisingly low energies of activation (DeltaG(double dagger) = 52-57 kJ mol(-1)) for even the bulky Si and Sn derivatives may be attributed to a widening of the exo-cyclic bond-angles of the diene carbons.

  DOI：

  10.1021/ja035136m

文献信息

• Ni-Catalyzed Stannylation of Aryl Esters via C−O Bond Cleavage
  作者：Yiting Gu、Rúben Martín

  DOI：10.1002/anie.201611720

  日期：2017.3.13

  Ni‐catalyzed stannylation of aryl esters with air‐ and moisture‐insensitive silylstannyl reagents via C −O cleavage is described. This protocol is characterized by its wide scope, including challenging combinations, thus enabling access to versatile building blocks and orthogonal C−heteroatom bond formations.

  描述了一种通过空气 裂解对水和不敏感的甲硅烷基锡烷基转移试剂进行镍催化的芳基酯的锡烷基化反应。该协议的特点是适用范围广，包括具有挑战性的组合，因此可以访问通用的构建基块和正交的C-杂原子键形成。
• Axial Chirality in 1,4-Disubstituted (<i>ZZ</i>)-1,3-Dienes. Surprisingly Low Energies of Activation for the Enantiomerization in Synthetically Useful Fluxional Molecules
  作者：Sandra Warren、Albert Chow、Gideon Fraenkel、T. V. RajanBabu

  DOI：10.1021/ja035136m

  日期：2003.12.1

  Trialkylsilyltrialkylstannes (R3Si-SnR'(3)) add to 1,6-diynes in the presence of Pd(0) and trispentaflurophenylphosphine to give 1,2-dialkylidenecyclopentanes with terminal silicon and tin substituents. The (ZZ)-geometry of these s-cis-1,3-dienes, resulting from the organometallic reaction mechanisms involved, forces the silicon and tin groups to be nonplanar, thus making the molecules axially chiral. There is rapid equilibration between the two helical forms at room-temperature irrespective of the size of the Si and Sn substituents. However, the two forms can be observed by H-1, C-13, and Sn-119 NMR spectroscopy at low temperature. The rates of enantiomerization, which depend on the Si and Sn substituents, and the substitution pattern of the cylopentane ring can be studied by dynamic NMR spectroscopy using line shape analysis. The surprisingly low energies of activation (DeltaG(double dagger) = 52-57 kJ mol(-1)) for even the bulky Si and Sn derivatives may be attributed to a widening of the exo-cyclic bond-angles of the diene carbons.