(E)-triethyl(2-(naphthalen-1-yl)vinyl)silane | 644998-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-triethyl(2-(naphthalen-1-yl)vinyl)silane
• 英文别名: triethyl-[(E)-2-naphthalen-1-ylethenyl]silane
• CAS: 644998-08-3
• 化学式: C₁₈H₂₄Si
• 分子量: 268.474
• InChiKey: IAKFTSURNZQWCD-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  三乙基乙烯基硅烷 、 氰基萘 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 六甲基二硅烷 、 三(4-氟苯基)磷化氢 作用下， 以 乙基环己烷 为溶剂， 反应 15.0h， 以88%的产率得到(E)-triethyl(2-(naphthalen-1-yl)vinyl)silane
  参考文献：
  名称：

  Rhodium-Catalyzed Alkenylation of Nitriles via Silicon-Assisted C−CN Bond Cleavage

  摘要：

  Rhodium-catalyzed Mizoroki-Heck type reaction of nitriles via the cleavage of C-C bonds is described. Orthogonal and iterative functionalizations of arenes were also demonstrated by combining the present and conventional halide-based cross-coupling reactions.

  DOI：

  10.1021/ol100481h

文献信息

• Metal-Free Catalytic Reductive Cleavage of Enol Ethers
  作者：Karina Chulsky、Roman Dobrovetsky

  DOI：10.1021/acs.orglett.8b02932

  日期：2018.11.2

  In contrast to the well-known reductive cleavage of the alkyl–O bond, the cleavage of the alkenyl–O bond is much more challenging especially using metal-free approaches. Unexpectedly, alkenyl–O bonds were reductively cleaved when enol ethers were reacted with Et3SiH and a catalytic amount of B(C6F5)3. Supposedly, this reaction is the result of a B(C6F5)3-catalyzed tandem hydrosilylation reaction and

  与众所周知的烷基-O键的还原裂解相反，烯基-O键的裂解更具挑战性，尤其是使用无金属方法时。出乎意料的是，当烯醇醚与Et 3 SiH和催化量的B（C 6 F 5）3反应时，烯基-O键被还原性裂解。据推测，该反应是B（C 6 F 5）3催化的串联氢化硅烷化反应和硅辅助的β-消除的结果。基于实验和密度泛函理论（DFT）计算，提出了这种裂解反应的机理。
• Water-Soluble N-Heterocyclic Carbene Platinum(0) Complexes: Recyclable Catalysts for the Hydrosilylation of Alkynes in Water at Room Temperature
  作者：Gustavo F. Silbestri、Juan Carlos Flores、Ernesto de Jesús

  DOI：10.1021/om300148q

  日期：2012.4.23

  The synthesis and characterization of new water-soluble platinum(0) complexes bearing sulfonated N-heterocyclic carbene (NHC) and divinyltetramethylsiloxane (dvtms) ligands are described. These complexes, of the general formula (NHC)Pt(dvtms), are active and recyclable catalysts for the hydrosilylation of phenylacetylene and other alkynes at room temperature in water. Our findings indicate that the

  描述了带有磺化N-杂环卡宾（NHC）和二乙烯基四甲基硅氧烷（dvtms）配体的新型水溶性铂（0）配合物的合成和表征。这些具有通式（NHC）Pt（dvtms）的配合物是在室温下在水中将苯乙炔和其他炔烃氢化硅烷化的活性和可循环使用的催化剂。我们的发现表明，尽管在纯水中高于80°C的温度下观察到水解，但在这些催化条件下NHC–Pt（0）键仍相当稳定。
• A recyclable and reusable K₂PtCl₄/Xphos-SO₃Na/PEG-400/H₂O system for highly regio- and stereoselective hydrosilylation of terminal alkynes
  作者：Caifeng Xu、Bin Huang、Tao Yan、Mingzhong Cai

  DOI：10.1039/c7gc02823g

  日期：——

  K2PtCl4/Xphos-SO3Na in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be a highly regio- and stereoselective catalyst for the hydrosilylation of terminal alkynes with hydrosilanes. The reaction could be conducted under mild conditions, yielding a variety of functionalized β-(E)-vinylsilanes in good to excellent yields with a total β-(E)-selectivity. The isolation of the products

  在聚（乙二醇）（PEG-400）和水的混合物中，K 2 PtCl 4 / Xphos-SO 3 Na被证明是高度炔和立体选择性的催化剂，用于末端炔烃与氢硅烷的硅氢化反应。该反应可以在温和的条件下进行，以良好的至优异的产率产生各种官能化的β-（E）-乙烯基硅烷，并具有总的β-（E）-选择性。产物的分离很容易通过环己烷萃取，更重要的是，在PEG-400 / H 2中用昂贵的K 2 PtCl 4和Xphos-SO 3 Na萃取。O系统可以轻松回收再利用至少八次，而不会损失任何催化活性。
• A highly regio- and stereoselective transition metal-catalyzed hydrosilylation of terminal alkynes under ambient conditions of air, water, and room temperature
  作者：Wei Wu、Chao-Jun Li

  DOI：10.1039/b302259e

  日期：——

  A highly efficient and stereoselective hydrosilylation of terminal alkynes was developed at room temperature in air and water.

  在室温下在空气和水中开发了末端炔烃的高效和立体选择性氢化硅烷化。
• Carbon supported hybrid catalysts for controlled product selectivity in the hydrosilylation of alkynes
  作者：Max Roemer、Vinicius R. Gonçales、Sinead T. Keaveney、Indrek Pernik、Jiaxin Lian、James Downes、J. Justin Gooding、Barbara A. Messerle

  DOI：10.1039/d0cy02136a

  日期：——

  A series of Rh- and Ir-hybrid catalysts with varying tether lengths has been prepared by immobilization of RhI, RhIII and IrIII complexes on carbon black via radical grafting. The performance of the different catalysts was assessed for the hydrosilylation of phenylacetylene with Et3SiH. The efficiency of the catalysts was dependent on the length of the tethers to the surface. The RhIII- and IrIII hybrids

  通过自由基接枝将Rh I，Rh III和Ir III配合物固定在炭黑上，制备了一系列具有不同系链长度的Rh和Ir杂化催化剂。评估了不同催化剂对苯乙炔与Et 3 SiH进行硅氢加成反应的性能。催化剂的效率取决于系链到表面的长度。如对于类似的均相Rh III催化剂所观察到的，Rh III-和Ir III杂化物提供了β（Z）-乙烯基硅烷。使用均相Rh I时未观察到明显的产物选择性前体作为催化剂。但是，在使用衍生自Rh I前体的Rh III杂化催化剂促进氢化硅烷化的过程中，主要产物为α-乙烯基硅烷，反应活性差异的根源是固定化过程中催化剂的化学修饰。证明了多种炔烃的底物范围，并提出了DFT计算支持的可行机理。