6-Amino-2-[[1-(3-triethoxysilylpropyl)triazol-4-yl]methyl]benzo[de]isoquinoline-1,3-dione | 1332499-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-Amino-2-[[1-(3-triethoxysilylpropyl)triazol-4-yl]methyl]benzo[de]isoquinoline-1,3-dione
• CAS: 1332499-45-2
• 化学式: C₂₄H₃₁N₅O₅Si
• 分子量: 497.626
• InChiKey: HOWUECPMGVZEHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-(叠氮基丙基)三乙氧基硅烷 、 N-propargyl-4-amino-1,8-naphthal-imide 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 生成 6-Amino-2-[[1-(3-triethoxysilylpropyl)triazol-4-yl]methyl]benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Tunable Multifunctional Mesoporous Silica Microdots Arrays by Combination of Inkjet Printing, EISA, and Click Chemistry

  摘要：

  A novel technique combining inkjet printing (IJP), evaporation-induced self-assembly (EISA), and click chemistry is implemented for elaborating mesoporous silica-based multifunctional microdots arrays. The microdots are in situ azide-functionalized with (3-azidopropyl)triethoxysilane (AzPTES). AzPTES is directly added to the initial sol before IJP and co-condenses with the silica precursor (TEOS) during the evaporation-induced self-assembly (EISA) of micelles on the substrate. After extracting the surfactants to release the porosity, model alkynes, namely propargyl alcohol, methyl pent-4-ynoate, ethynylferrocene, and N-propargyl-4-amino-1,8-naphthalimide, are grafted by the azide-alkyne CuAAC click reaction. The demonstration is established that the click reaction is nearly quantitative and occurs in the whole volume of the microdots attesting the accessibility of the azide groups. By integrating an alkyne-containing silylated precursor in a similar route, azide-containing functional groups are anchored in the microdots by click reaction. A demonstration of the multifunctionalization of such microdots arrays is achieved by reacting clickable dyes on alternate alkyne- and azide-functionalized lines of microdots, as evidenced by confocal fluorescence microscopy. Such multifunctional mesoporous silica microdots arrays offer promising perspectives for biosensing applications.

  DOI：

  10.1021/cm3022769

文献信息

• Click Approaches to Functional Water-Sensitive Organotriethoxysilanes
  作者：Kristýna Bürglová、Nirmalya Moitra、Jana Hodačová、Xavier Cattoën、Michel Wong Chi Man

  DOI：10.1021/jo201484n

  日期：2011.9.16

  The derivatization of functional organic fragments with triethoxysilyl groups to afford hydrolyzable organosilanes with targeted properties using the copper-catalyzed alkyne azide cydoaddition reaction under strictly anhydrous conditions is described according to two approaches, starting from five silylated substrates. This high yield, fast, and selective method is applicable to a wide range of substrates and is expected to lead to important achievements in the field of functional hybrid silica.