(E)-1-dimethyl(phenyl)silyl-2-trimethylsilylethene | 110838-66-9

• 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: (E)-1-dimethyl(phenyl)silyl-2-trimethylsilylethene
• 英文别名: dimethyl-phenyl-[(E)-2-trimethylsilylethenyl]silane
• CAS: 110838-66-9
• 化学式: C₁₃H₂₂Si₂
• 分子量: 234.489
• InChiKey: YKURLBODQNNCHP-VAWYXSNFSA-N

物化性质

• 沸点：
  80 °C(Press: 2 Torr)
• 密度：
  0.86±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (E)-1-dimethyl(phenyl)silyl-2-trimethylsilylethene 、 乙酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以49%的产率得到(E)-4-(dimethylphenylsilyl)-3-buten-2-one
  参考文献：
  名称：

  Barbero, Asuncion; Cuadrado, Purificacion; Fleming, Ian, Journal of the Chemical Society. Perkin transactions I, 1995, # 12, p. 1525 - 1532

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl(phenyl)silyllithium 、 三甲基乙炔基硅 生成 (E)-1-dimethyl(phenyl)silyl-2-trimethylsilylethene
  参考文献：
  名称：

  The synthesis of 3-trimethylsilyl-4-dimethyl(phenyl)silylbut-3-en-2-one, a β-functionalised Michael acceptor

  摘要：

  The title compound 3 has been prepared by silyl-cupration of trimethylsilylacetylene followed by acetylation. The phenyidimethylsilyl group can be removed selectively in a three-step procedure to give 3-trimethylsilylbut-3-ene-2-one lb. The enone 3 and cyclohexanone can be used in an annelation reaction to make 5-dimethyl(phenyl)silylbicyclo[4.4.0]decan-3-one 20 and hence to make 2-vinylcyclohexylacetic acid 23.

  DOI：

  10.1016/s0040-4020(01)80457-9

文献信息

• Highly selective hydrosilylation of olefins and acetylenes by platinum(0) complexes bearing bulky N-heterocyclic carbene ligands
  作者：P. Żak、M. Bołt、M. Kubicki、C. Pietraszuk

  DOI：10.1039/c7dt04392a

  日期：——

  Platinum complexes bearing bulky N-heterocyclic carbene (NHC) ligands, i.e., [Pt(IPr*)(dvtms)] (where, IPr* = 1,3-bis2,6-bis(diphenylmethyl)-4-methylphenyl}imidazol-2-ylidene) and [Pt(IPr*OMe)(dvtms)] (where, IPr*OMe = 1,3-bis2,6-bis(diphenylmethyl)-4-methoxyphenyl}imidazol-2-ylidene, dvtms = divinyltetramethyldisiloxane) catalyse nearly quantitatively and highly or completely the selective hydrosilylation

  带有大体积N-杂环卡宾（NHC）配体的铂络合物，即[Pt（IPr *）（dvtms）]（其中IPr * = 1,3-双2,6-双（二苯基甲基）-4-甲基苯基}咪唑-2-亚烷基）和[Pt（IPr * OMe）（dvtms）]（其中IPr * OMe = 1,3-双2,6-双（二苯甲基）-4-甲氧基苯基}咪唑-2-亚基， dvtms =二乙烯基四甲基二硅氧烷）几乎定量且高度或完全催化末端烯烃以及末端或内部乙炔的选择性氢化硅烷化。
• The cobalt(II) complex of a new tridentate Schiff-base ligand as a catalyst for hydrosilylation of olefins
  作者：Adam Gorczyński、Maciej Zaranek、Samanta Witomska、Aleksandra Bocian、Artur R. Stefankiewicz、Maciej Kubicki、Violetta Patroniak、Piotr Pawluć

  DOI：10.1016/j.catcom.2016.02.009

  日期：2016.3

  new, tridentate Schiff-base ligand L, which readily reacts with CoCl2 to form a monometallic [CoLCl2] complex that, upon reduction, functions as active hydrosilylation catalyst. The ligand and the [CoLCl2] catalyst have been characterized spectroscopically (MS, NMR, FTIR) and by single crystal X-ray diffraction techniques. The results of preliminary catalytic experimentation show that the cobalt complex

  1-甲基-2-咪唑甲醛与2-（1-甲基肼基）吡啶的缩合导致合成新的三齿席夫碱配体L，该配体容易与CoCl 2反应形成单金属[Co L Cl 2 ]配合物还原后，用作活性氢化硅烷化催化剂。所述配体和[Co L Cl 2 ]催化剂已经通过光谱法（MS，NMR，FTIR）和通过单晶X射线衍射技术进行了表征。初步催化实验的结果表明，取决于所用的氢硅烷底物，钴配合物可引起烯烃的氢化硅烷化和脱氢甲硅烷基化。
• Copper(<scp>ii</scp>)-catalyzed highly regio- and stereo-selective hydrosilylation of unactivated internal alkynes with silylborate in water
  作者：Qing-Qing Xuan、Chuan-Li Ren、Li Liu、Dong Wang、Chao-Jun Li

  DOI：10.1039/c5ob00694e

  日期：——

  The highly regio- and stereoselective hydrosilylation of internal alkynes with silylborate catalyzed by Cu(OTf)2 with 1,10-phenanthroline as the ligand in the presence of Cs2CO3 in water is developed. This protocol was applied efficiently in the aqueous synthesis of multi-substituted vinylsilanes.

  在水中存在Cs 2 CO 3的情况下，开发了以1,10-菲咯啉为配体的Cu（OTf）2催化内部炔烃与甲硅烷基硼酸酯的高度区域选择性和立体选择性氢化硅烷化反应。该方案有效地应用于多取代乙烯基硅烷的水合成中。
• Selective Hydrosilylation of 1-Alkynes Using Iridium Catalyst with Biphosphinine Ligand
  作者：Yoshihiro Miyake、Eigo Isomura、Masahiko Iyoda

  DOI：10.1246/cl.2006.836

  日期：2006.8

  The iridium-catalyzed hydrosilylation of alkynes in the presence of 4,4′,5,5′-tetramethylbiphosphinine (tmbp) has been explored. The hydrosilylation of alkynes in the presence of tmbp proceeds effectively to give β-(E)-vinylsilanes highly selectively in moderate to high yields, whereas a similar hydrosilylation in the absence of tmbp produces β-(Z)-vinylsilanes selectively. The stereoselectivity of these reactions suggests the importance of the electron-withdrawing properties of tmbp coordinated to iridium.

  我们探索了在 4,4′,5,5′-四甲基二膦（tmbp）存在下铱催化的炔烃氢硅化反应。在有 tmbp 存在的情况下，炔烃的氢硅化反应能有效地进行，从而以中等到较高的产率高选择性地生成 β-(E)-乙烯基硅烷，而在没有 tmbp 存在的情况下，类似的氢硅化反应则能选择性地生成 β-(Z)-乙烯基硅烷。这些反应的立体选择性表明了与铱配位的 tmbp 的吸电子特性的重要性。
• Insertion of vinylsilane into the ruthenium–silicon bond—direct evidence for the non-metallacarbene mechanism of silylalkene disproportionation
  作者：Bogdan Marciniec、Cezary Pietraszuk

  DOI：10.1039/c39950002003

  日期：——

  The reversible insertion of the vinylsilane molecule into the Ru–Si bond occurs in two different ways to give E-1,2-bis(silyl)ethene and 1,1-bis(silyl)ethene which, in combination with the previous experiments by Wakatsuki et al., provides convincing evidence for a non-metallacarbene mechanism of silylalkene disproportionation.

  乙烯基硅烷分子以两种不同的方式可逆地插入 RuâSi 键，生成 E-1,2-双（硅烷基）乙烯和 1,1-双（硅烷基）乙烯，结合 Wakatsuki 等人之前的实验，为硅烷歧化的非金属碳化机制提供了令人信服的证据。