(3-(benzylthio)propyl)triethoxysilane

• 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: (3-(benzylthio)propyl)triethoxysilane
• 英文别名: 3-Benzylsulfanylpropyl(triethoxy)silane
• 化学式: C₁₆H₂₈O₃SSi
• 分子量: 328.548
• InChiKey: VRVARBOMFPFVIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  烯丙基三乙氧基硅烷 、 苄硫醇 在 安息香双甲醚 作用下， 反应 24.0h， 生成 (3-(benzylthio)propyl)triethoxysilane
  参考文献：
  名称：

  Thiol–ene Click Reaction as a General Route to Functional Trialkoxysilanes for Surface Coating Applications

  摘要：

  Functionalized trialkoxysilanes are widely used to modify the surface properties of materials and devices. It will be shown that the photoinitiated radical-based thiol-ene "click" reaction provides a simple and efficient route to diverse trialkoxysilanes. A total of 15 trialkoxysilanes were synthesized by reacting either alkenes with 3-mercaptopropyltrialkoxysilane or thiols with allyltrialkoxysilanes in the presence of a photoinitiator. The functionalized trialkoxysilanes were obtained in quantitative to near-quantitative yields with high purity. The photochemical reactions can be run neat in standard borosilicate glassware using a low power 15-W blacklight. A wide range of functional groups is tolerated in this approach, and even complex alkenes click with the silane precursors. To demonstrate that these silanes can be used as surface coating agents, several were reacted with iron oxide superparamagnetic nanoparticles and the loadings quantified. The photoinitiated thiol-ene reaction thus offers a facile and efficient method for preparing surface-active functional trialkoxysilanes.

  DOI：

  10.1021/ja202292q

文献信息

• Iridium-Catalyzed Hydrosilylation of Unactivated Alkenes: Scope and Application to Late-Stage Functionalization
  作者：Xingze Xie、Xueyan Zhang、Haoyu Yang、Xin Ji、Jianing Li、Shengtao Ding

  DOI：10.1021/acs.joc.8b02838

  日期：2019.1.18

  Highly efficient and general Ir-catalyzed hydrosilylation of unactivated alkenes with excellent anti-Markovnikov regioselectivity was described. A broad scope of hydrosilylated products were synthesized economically and conveniently from commercially or naturally available compounds, which provides versatile valuable precursors for organic and medicinal studies.
• Thiol–ene Click Reaction as a General Route to Functional Trialkoxysilanes for Surface Coating Applications
  作者：Alexander K. Tucker-Schwartz、Richard A. Farrell、Robin L. Garrell

  DOI：10.1021/ja202292q

  日期：2011.7.27

  Functionalized trialkoxysilanes are widely used to modify the surface properties of materials and devices. It will be shown that the photoinitiated radical-based thiol-ene "click" reaction provides a simple and efficient route to diverse trialkoxysilanes. A total of 15 trialkoxysilanes were synthesized by reacting either alkenes with 3-mercaptopropyltrialkoxysilane or thiols with allyltrialkoxysilanes in the presence of a photoinitiator. The functionalized trialkoxysilanes were obtained in quantitative to near-quantitative yields with high purity. The photochemical reactions can be run neat in standard borosilicate glassware using a low power 15-W blacklight. A wide range of functional groups is tolerated in this approach, and even complex alkenes click with the silane precursors. To demonstrate that these silanes can be used as surface coating agents, several were reacted with iron oxide superparamagnetic nanoparticles and the loadings quantified. The photoinitiated thiol-ene reaction thus offers a facile and efficient method for preparing surface-active functional trialkoxysilanes.