N-(quinuclidin-3-yl)undec-10-enamide | 864971-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: N-(quinuclidin-3-yl)undec-10-enamide
• 英文别名: N-(1-azabicyclo[2.2.2]octan-3-yl)undec-10-enamide
• CAS: 864971-55-1
• 化学式: C₁₈H₃₂N₂O
• 分子量: 292.465
• InChiKey: CXCNZTPSMIPKCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-巯丙基三乙氧基硅烷 、 N-(quinuclidin-3-yl)undec-10-enamide 在 安息香双甲醚 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 N-((1s,4s)-quinuclidin-3-yl)-11-((3-(triethoxysilyl)propyl)thio)undecanamide
  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
• 作为产物：
  描述：

  2-十一烯酸 、 3-aminoquinuclidine dihydrochloride 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以23%的产率得到N-(quinuclidin-3-yl)undec-10-enamide
  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

• SYNTHESIS OF THIOETHER CONTAINING TRIALKOXYSILANES
  申请人：Garrell Robin L.

  公开号：US20130345412A1

  公开（公告）日：2013-12-26

  The invention relates to a radical-initiated thiol-ene or thiol-yne “click” reaction that provides a simple and efficient route to diverse trialkoxysilanes. Trialkoxysilanes made in this way are obtained in quantitative to near-quantitative yields with high purity without any or minimal purification. A wide range of functional groups is tolerated in this approach, and even complex alkenes click with the silane precursors. The modular nature of these radical-based thiol-ene or thiol-yne “click” reactions allows a wide variety of pendant groups to be coupled to silane compounds that can then be coupled to a wide variety surfaces in order to modify their material properties. Consequently, such radical initiated thiol-ene and thiol-yne reactions provide facile and efficient methods for preparing an enormous number of surface-active functional trialkoxysilanes.

  该发明涉及一种基于自由基的巯基-烯或巯基-炔“点击”反应，提供了一种简单和高效的途径来制备多样化的三烷氧基硅烷。通过这种方法制备的三烷氧基硅烷可以在无需或最小程度的纯化下以定量至接近定量的收率和高纯度获得。这种方法可以容忍各种功能基团，甚至复杂的烯烃也可以与硅烷前体进行点击反应。这种基于自由基的巯基-烯或巯基-炔“点击”反应的模块化特性允许将各种侧链基团耦合到硅烷化合物上，然后将其耦合到各种表面上以修改其材料性能。因此，这种基于自由基的巯基-烯或巯基-炔反应提供了一种简便高效的方法，用于制备大量表面活性功能三烷氧基硅烷。
• Synthesis of thioether containing trialkoxysilanes
  申请人：Garrell Robin L.

  公开号：US09175026B2

  公开（公告）日：2015-11-03

  The invention relates to a radical-initiated thiol-ene or thiol-yne “click” reaction that provides a simple and efficient route to diverse trialkoxysilanes. Trialkoxysilanes made in this way are obtained in quantitative to near-quantitative yields with high purity without any or minimal purification. A wide range of functional groups is tolerated in this approach, and even complex alkenes click with the silane precursors. The modular nature of these radical-based thiol-ene or thiol-yne “click” reactions allows a wide variety of pendant groups to be coupled to silane compounds that can then be coupled to a wide variety surfaces in order to modify their material properties. Consequently, such radical initiated thiol-ene and thiol-yne reactions provide facile and efficient methods for preparing an enormous number of surface-active functional trialkoxysilanes.

  本发明涉及一种基于自由基引发的巯基-烯或巯基-炔“点击”反应，该反应提供了一种简单高效的途径来制备多样化的三烷氧基硅烷。以这种方式制备的三烷氧基硅烷可以在无需或最小程度净化的情况下以高纯度和量化至近量化产率获得。这种方法可以容忍多种功能基团，甚至复杂的烯烃也可以与硅烷前体进行“点击”反应。这种基于自由基的巯基-烯或巯基-炔“点击”反应的模块化特性允许将各种挂链基团耦合到硅烷化合物中，然后将其耦合到各种表面上以改变其材料性能。因此，这种基于自由基引发的巯基-烯或巯基-炔反应为制备大量表面活性功能三烷氧基硅烷提供了简便高效的方法。
• [EN] SYNTHESIS OF THIOETHER CONTAINING TRIALKOXYSILANES<br/>[FR] SYNTHÈSE DE TRIALCOXYSILANES CONTENANT DES THIOÉTHERS
  申请人：UNIV CALIFORNIA

  公开号：WO2012129380A3

  公开（公告）日：2012-12-06
• US9175026B2
  申请人：——

  公开号：US9175026B2

  公开（公告）日：2015-11-03
• 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.