(5-azidopentyl)triethoxysilane | 882686-49-9

• 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: (5-azidopentyl)triethoxysilane
• 英文别名: 5-Azidopentyl(triethoxy)silane
• CAS: 882686-49-9
• 化学式: C₁₁H₂₅N₃O₃Si
• 分子量: 275.423
• InChiKey: UADXFGRXKSYOLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5-azidopentyl)triethoxysilane 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 0.33h， 以78%的产率得到1-戊胺,5-(三乙氧基甲硅烷基)-
  参考文献：
  名称：

  A simple access to ω-aminoalkyltrialkoxysilanes: Tunable linkers for self-organised organosilicas

  摘要：

  A simple route to omega-aminoalkyltriethoxysilanes with variable alkylene chain lengths, (EtO)(3)Si(CH2)(n)NH2 (n = 5, 11) is described. These silyl linkers have been used to prepare urea-based compounds with H-bonding and hydrophobic interactions which enable the self-assembly of the molecules. These molecular precursors are suitable for the obtention of nano-structured hybrid silicas. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.11.036
• 作为产物：
  描述：

  (5-bromopentyl)triethoxysilane 在 sodium azide 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以91%的产率得到(5-azidopentyl)triethoxysilane
  参考文献：
  名称：

  正交点击反应制备双功能介孔二氧化硅纳米粒子及其在协同催化中的应用

  摘要：

  描述了双功能介孔二氧化硅纳米粒子的合成。通过将四乙氧基硅烷与两个正交官能化的三乙氧基烷基硅烷共缩合，可在介孔二氧化硅中引入两个化学正交的官能度。后功能化是通过正交表面化学实现的。硫醇-烯反应，Cu催化的1,3-偶极炔烃/叠氮化物环加成反应和自由基一氧化氮交换反应被用作正交过程，以在表面上安装两种反应性不同的官能团。讨论了通过这种方法制备带有酸性和碱性位点的介孔二氧化硅纳米粒子。颗粒通过固态NMR光谱，元素分析，红外光谱和扫描电子显微镜进行分析。作为第一个应用程序，

  DOI：

  10.1002/chem.201200499

文献信息

• Bifunctional mesoporous silica nanoparticles as cooperative catalysts for the Tsuji–Trost reaction – tuning the reactivity of silica nanoparticles
  作者：Arne T. Dickschat、Frederik Behrends、Sabrina Surmiak、Mark Weiß、Hellmut Eckert、Armido Studer

  DOI：10.1039/c3cc00235g

  日期：——

  Bifunctional mesoporous silica nanoparticles (MSNs) bearing Pd-complexes and additional basic sites were prepared and tested as cooperative active catalysts in the Tsuji–Trost allylation of ethyl acetoacetate. Functionalization of the MSNs was realized by postmodification using click-chemistry. The selectivity of mono versus double allylation was achieved by control of reaction temperature and the nature of the catalyst.

  具有Pd配合物和额外碱性位点的双功能介孔二氧化硅纳米粒子（MSNs）被制备并测试作为协同活性催化剂，用于乙酰乙酸乙酯的Tsuji-Trost烯丙基化反应。通过点击化学后修饰实现了MSNs的功能化。单烯丙基化和双烯丙基化反应的选择性通过控制反应温度和催化剂性质来实现。
• Preparation of Bifunctional Mesoporous Silica Nanoparticles by Orthogonal Click Reactions and Their Application in Cooperative Catalysis
  作者：Arne T. Dickschat、Frederik Behrends、Martin Bühner、Jinjun Ren、Mark Weiß、Hellmut Eckert、Armido Studer

  DOI：10.1002/chem.201200499

  日期：2012.12.21

  The synthesis of bifunctional mesoporous silica nanoparticles is described. Two chemically orthogonal functionalities are incorporated into mesoporous silica by co‐condensation of tetraethoxysilane with two orthogonally functionalized triethoxyalkylsilanes. Post‐functionalization is achieved by orthogonal surface chemistry. A thiol–ene reaction, Cu‐catalyzed 1,3‐dipolar alkyne/azide cycloaddition,

  描述了双功能介孔二氧化硅纳米粒子的合成。通过将四乙氧基硅烷与两个正交官能化的三乙氧基烷基硅烷共缩合，可在介孔二氧化硅中引入两个化学正交的官能度。后功能化是通过正交表面化学实现的。硫醇-烯反应，Cu催化的1,3-偶极炔烃/叠氮化物环加成反应和自由基一氧化氮交换反应被用作正交过程，以在表面上安装两种反应性不同的官能团。讨论了通过这种方法制备带有酸性和碱性位点的介孔二氧化硅纳米粒子。颗粒通过固态NMR光谱，元素分析，红外光谱和扫描电子显微镜进行分析。作为第一个应用程序，
• Pd Immobilized in Mesoporous Silica Particles as Recyclable Catalysts for Suzuki-Miyaura Coupling: Cooperative Effects Exerted by Co-Immobilized Amine Functionalities
  作者：Armido Studer、Arne Dickschat、Sabrina Surmiak

  DOI：10.1055/s-0033-1339183

  日期：——

  A bifunctional heterogeneous palladium catalyst bearing additional basic sites was successfully prepared by sequential Cu-catalyzed 1,3-dipolar alkyne-azide cycloaddition and thermal nitroxide-exchange reaction of surface-bound alkoxyamines. This catalyst shows high activity in the Suzuki-Miyaura cross-coupling. The additional basic functionality acts cooperatively since an analogous heterogeneous Pd catalyst lacking the amine functionality is less active. Such catalysts can be recycled up to ten times without loss of activity.
• Palladium Nanoparticle Loaded Bifunctional Silica Hybrid Material: Preparation and Applications as Catalyst in Hydrogenation Reactions
  作者：Sabrina K. Surmiak、Carsten Doerenkamp、Philipp Selter、Martin Peterlechner、Andreas H. Schäfer、Hellmut Eckert、Armido Studer

  DOI：10.1002/chem.201604508

  日期：2017.5.2

  Bifunctional mesoporous silica was prepared by co‐condensation of tetraethyl orthosilicate (TEOS) with functionalized organosilanes containing azides or alkoxyamines. Orthogonal functional groups at the particles were selectively addressed in subsequent chemical modifications through “click”‐chemistry (“click to ligand” strategy) and radical nitroxide exchange. Palladation with PdCl2 delivered Pd nanoparticle‐loaded

  双功能介孔二氧化硅是通过将原硅酸四乙酯（TEOS）与含有叠氮化物或烷氧基胺的功能化有机硅烷进行缩聚反应制得的。在随后的化学修饰中，通过“点击”-化学反应（“点击键合配体”策略）和自由基一氧化氮交换，选择性地处理了颗粒上的正交官能团。Palladation用的PdCl 2输送Pd纳米颗粒的加载的二氧化硅材料轴承亚砜和附加氨基酰胺作为在原位还原的Pd借助于稳定配体II-盐。这些功能性颗粒已成功应用于炔烃和烯烃的氢化。这些杂化催化剂在温和条件下实现了醛加氢脱氧和苄基醚裂解。通过IR，TEM / STEM，EDX和固态NMR光谱分析了颗粒。
• A simple access to ω-aminoalkyltrialkoxysilanes: Tunable linkers for self-organised organosilicas
  作者：Benoît P. Pichon、Michel Wong Chi Man、Catherine Bied、Joël J.E. Moreau

  DOI：10.1016/j.jorganchem.2005.11.036

  日期：2006.3

  A simple route to omega-aminoalkyltriethoxysilanes with variable alkylene chain lengths, (EtO)(3)Si(CH2)(n)NH2 (n = 5, 11) is described. These silyl linkers have been used to prepare urea-based compounds with H-bonding and hydrophobic interactions which enable the self-assembly of the molecules. These molecular precursors are suitable for the obtention of nano-structured hybrid silicas. (c) 2005 Elsevier B.V. All rights reserved.