1-(4-溴苯基)乙氧基三乙基硅烷 | 855418-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-溴苯基)乙氧基三乙基硅烷
• 英文名称: [1-(4-bromophenyl)ethoxy](triethyl)silane
• 英文别名: [1-(4-bromophenyl)ethoxy]triethylsilane；Silane, [1-(4-bromophenyl)ethoxy]triethyl-；1-(4-bromophenyl)ethoxy-triethylsilane
• CAS: 855418-49-4
• 化学式: C₁₄H₂₃BrOSi
• 分子量: 315.326
• InChiKey: HLNQVMBMAFBUNC-UHFFFAOYSA-N

物化性质

• 沸点：
  323.1±17.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三乙基硅烷 、 4-溴苯乙酮 在 [L(2H)AlMe]+[MeB(C6F5)3]- 作用下， 反应 12.0h， 以80%的产率得到1-(4-溴苯基)乙氧基三乙基硅烷
  参考文献：
  名称：

  有机铝阳离子催化羰基、烯烃和炔烃的选择性氢化硅烷化

  摘要：

  已经报道了带有N , N'螯合的共轭双胍盐 (CBG)的三配位铝甲基阳离子。已经研究了它在催化多种羰基、烯烃和炔烃的氢化硅烷化中的应用。此外，已经检查了它在可还原官能团存在下催化醛的化学选择性氢化硅烷化的行为。

  DOI：

  10.1002/ejic.202101030

文献信息

• Alkylfluorenyl substituted N-heterocyclic carbenes in copper(<scp>i</scp>) catalysed hydrosilylation of aldehydes and ketones
  作者：Matthieu Teci、Nicolas Lentz、Eric Brenner、Dominique Matt、Loïc Toupet

  DOI：10.1039/c5dt01888a

  日期：——

  Copper(I) complexes featuring N-heterocyclic carbenes (NHCs) in which the nitrogen atoms are substituted by a 9-ethyl-9-fluorenyl group (EF) have been synthesised and tested in the hydrosylilation of functionalized and/or sterically demanding ketones and aldehydes. These reactions, carried out with triethylsilane as hydride source, were best achieved with the imidazolylidene copper complex 2d in which

  合成并测试了N-杂环卡宾（NHC）（其中的氮​​原子被9-乙基-9-芴基（EF）取代）的铜（I）配合物，并在官能化和/或空间需求的酮的加氢水解反应中进行了测试。醛。用三乙基硅烷作为氢化物源进行的这些反应最好用咪唑基亚烷基铜络合物2d来完成其中EF取代基可以围绕相应的N–CEF键自由旋转。活性物种的出色稳定性超过了先前报道的Cu–NHC催化剂的稳定性，这可能取决于NHC侧臂在催化循环过程中通过形成夹心状中间体来保护铜中心的能力，还取决于其空间柔性，便于采用承压物。吨数达到1000。
• A Simple and Efficient Copper-Catalyzed Procedure for the Hydrosilylation of Hindered and Functionalized Ketones
  作者：Silvia Díez-González、Harneet Kaur、Fabiano Kauer Zinn、Edwin D. Stevens、Steven P. Nolan

  DOI：10.1021/jo050397v

  日期：2005.6.1

  The catalytic hydrosilylation of highly hindered and functionalized ketones is described. The combination of inexpensive catalyst precursors, CuCl and NHC-HX (NHC = N-heterocyclic carbene), leads to a highly efficient reduction mediator for the preparation of silyl ethers from unfunctionalized and functionalized alkyl, cyclic, bicyclic, aromatic, and heteroaromatic ketones. A series of catalyst precursors have been structurally characterized and a catalyst-structure activity relationship is discussed.
• 10.1002/ejoc200900066
  作者：Bach, Peter、Albright, Andrea、Laali, Kenneth K.

  DOI：10.1002/ejoc200900066

  日期：——
• Copper (I) 1,3-R2-3,4,5,6-tetrahydropyrimidin-2-ylidenes (R=mesityl, 2-propyl): synthesis, X-ray structures, immobilization and catalytic activity
  作者：Bhasker Bantu、Dongren Wang、Klaus Wurst、Michael R. Buchmeiser

  DOI：10.1016/j.tet.2005.07.116

  日期：2005.12

  The synthesis of novel copper (1) N-heterocyclic carbene complexes is described. Thus, reaction of CuX with 1,3-di(2-propyl)3,4,5,6-tetrahydropyrimidin-2-ylidene yields CuX(1,3-di(2-propyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene) (X=Cl, (1a), Br (1b)); however, reaction of CuCl with 1,3-dimesityl-3,4,5,6-tetrahydropyrimidin-2-ylidene yields the bis-N-heterocylcic carbene complex Cu(1,3-dimesityl-3,4,5,6-tetrahydropyrimidin-2-ylidene)(2)(+) CuBr2-(2). A supported version of 1, i.e. PS-DVB-CH2-OCO-CF2-CF2-CF2-COOCu(1,3-di(2-propyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene) (3) was prepared from I and PS-DVB-CH2-OCO-CF2-CF2-CF2-COOAg. A copper loading of 4.15 mu mol/g was realized. The new compounds were used as catalysts in carbonyl hydrosilylation and cyanosilylation reactions. Excellent reactivity was observed, giving raise to turn-over numbers (TONs) of up to 100,000. Compounds 1a, 1b, and 2 have also been used as catalysts for the atom transfer radical polymerization (ATRP) of methyl methacrylate (MMA). A linear conversion of monomer with time was observed, however, no control over molecular weight of PMMA was observed. (c) 2005 Elsevier Ltd. All rights reserved.
• Organoaluminum Cation Catalyzed Selective Hydrosilylation of Carbonyls, Alkenes, and Alkynes
  作者：Nabin Sarkar、Rajata Kumar Sahoo、Sayantan Mukhopadhyay、Sharanappa Nembenna

  DOI：10.1002/ejic.202101030

  日期：2022.3.18

  methyl cation bearing N,N′-chelated conjugated-bis-guanidinate (CBG) has been reported. Its use in the catalysis of the hydrosilylation of a wide array of carbonyls, alkenes, and alkynes has been investigated. In addition, its behavior in the catalysis of the chemoselective hydrosilylation of aldehydes in the presence of reducible functional groups has been examined.

  已经报道了带有N , N'螯合的共轭双胍盐 (CBG)的三配位铝甲基阳离子。已经研究了它在催化多种羰基、烯烃和炔烃的氢化硅烷化中的应用。此外，已经检查了它在可还原官能团存在下催化醛的化学选择性氢化硅烷化的行为。