3-azidopropyldimethallyl(methyl)silane | 1008132-76-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-azidopropyldimethallyl(methyl)silane
• 英文别名: 3-Azidopropylmethyldimethallylsilane；3-azidopropyl-methyl-bis(2-methylprop-2-enyl)silane
• CAS: 1008132-76-0
• 化学式: C₁₂H₂₃N₃Si
• 分子量: 237.42
• InChiKey: XMSAYAUZKGDQSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-azidopropyldimethallyl(methyl)silane 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以75%的产率得到3-aminopropyldimethallyl(methyl)silane
  参考文献：
  名称：

  Sc（OTf）3介导的固体表面羟基官能团的甲硅烷基化：在室温下进行的催化接枝方法。

  摘要：

  DOI：

  10.1002/anie.200703112
• 作为产物：
  描述：

  (3-chloropropyl)(methyl)bis(2-methylallyl)silane 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以92%的产率得到3-azidopropyldimethallyl(methyl)silane
  参考文献：
  名称：

  N-羟基琥珀酰亚胺酯修饰玻璃表面的酸一步法及其在构建用于研究生物分子相互作用的微阵列中的应用

  摘要：

  由于微阵列技术可作为用于生物分子相互作用的高通量分析和鉴定与生物分子结合的生物活性物质的强大工具，因此备受关注。当前用于构建微阵列的大多数方法都依赖于将物质固定在适当衍生化的表面上。在用于此目的的各种官能团中，N-羟基琥珀酰亚胺（NHS）酯基已被广泛使用，因为它可以很容易地与目标物质中的胺或酰肼官能团反应。然而，通常通过采用不方便且费时的多步骤方法将NHS酯基引入到载玻片的表面上。在最近的研究中，我们开发了一种高效的一步法，利用NHS酯基团衍生化玻璃表面，该方法利用了NHS酯官能化的二甲基烯丙基硅烷与玻璃表面上的硅烷醇的酸介导反应。利用TfOH而非Sc（OTf）3进行表面改性的条件被发现是优越的。蛋白质和RNA结合实验表明，采用这种方法修饰的玻璃表面适用于有效固定由胺，酰肼和醇官能团附加的各种物质。以这种方式生成的微阵列适用于蛋白质，蛋白质，聚糖，蛋白质小分子和肽RNA相互作用的快速分析程

  DOI：

  10.1021/bc100042j

文献信息

• Facile One-Step Catalytic Grafting of N-Hydroxysuccinimidyl-Ester-Functionalized Methallylsilane onto Silica for Enzyme Immobilization
  作者：Un-Young Jung、Jung-Woo Park、Eun-Hee Han、Sin-Gun Kang、Sera Lee、Chul-Ho Jun

  DOI：10.1002/asia.201000713

  日期：2011.2.1

  A one‐step grafting method of NHS‐ester group is described for the immobilization of enzymes onto a silica surface at room temperature. Pure NHS‐ester functionalized methallylsilane was prepared as a grafting reagent and showed remarkable grafting efficiency with acid catalysts at room temperature. As a result, mesoporous silica balls bearing a covalently immobilized enzyme could be obtained with a

  描述了一种在室温下将酶固定在二氧化硅表面上的NHS酯基的一步接枝方法。制备了纯NHS酯官能化的甲基烯丙基硅烷作为接枝剂，并在室温下显示出显着的用酸催化剂的接枝效率。结果，与常规的多步接枝方法相比，可以以高负载率获得带有共价固定化酶的中孔二氧化硅球。此一步步骤的优点是可以精确测量NHS-酯基团的高负载效率，并且仅形成NHS-酯基团，从而减少了未反应的官能团的存在。
• 수분에 안정한 알릴실란화 포스포릴콜린의 제조방법
  申请人：UNIVERSITY INDUSTRY FOUNDATION, YONSEI UNIVERSITY WONJU CAMPUS 연세대학교 원주산학협력단(120120107738) Corp. No ▼ 141271-0004893BRN ▼224-82-14988

  公开号：KR20160107442A

  公开（公告）日：2016-09-19

  본 발명은 말단에 알킨기가 도입된 포스포릴콜린(phosphorylcholine, PC)을 클릭화학(click chemistry) 반응에 따라 구리 촉매 존재 하에서 아자이드 화합물과 반응시켜 말단에 기능성기가 도입된 알릴실란화 포스포릴콜린을 제조하는 단계를 포함하는, 포스포릴콜린의 말단 기능화 방법에 관한 것으로서, 본 발명에서는 구리-촉매 클릭 반응을 통해 알릴실란화 포스포릴콜린(Allylsilanated phosphorylcholines), 보다 구체적으로는 메트알릴실란화 포스포릴콜린(Methallylsilanated phosphorylcholines, MASPCs)을 합성하는 방법을 제공함으로써, 수성 시스템(aqueous system)에서도 반응이 잘 진행되고, 넓은 온도 범위 및 pH 범위에서도 높은 수율로 알릴실란화 포스포릴콜린을 수득하며, 반응과정에서 기능성기(functional group)가 모두 안전하게 보존될 수 있는 제조방법을 제공하고자 한다.

  本发明涉及一种对磷酸胆碱进行末端官能化的方法，其中在点击化学反应中利用铜催化剂使末端带有功能基团的丙烯基硅烷化磷酸胆碱合成，该方法包括制备在末端引入有丙烯基硅烷的磷酸胆碱，该方法通过铜催化的点击反应合成丙烯基硅烷化磷酸胆碱（Allylsilanated phosphorylcholines），更具体地说，提供了一种合成甲基丙烯基硅烷化磷酸胆碱（Methallylsilanated phosphorylcholines，MASPCs）的方法，使反应在水性系统中进行，可以在广泛的温度和pH范围内高产率地获得丙烯基硅烷化磷酸胆碱，并提供了一种制备方法，可以安全地保留所有功能基团。
• Synthesis and application of moisture-stable methallylsilanated phosphorylcholine as a surface modifier
  作者：Lei Liu、Jun Hyun Song、Myong Euy Lee、Ye Ri Han、Chul-Ho Jun

  DOI：10.1016/j.tetlet.2014.09.076

  日期：2014.11

  New methallylsilanated phosphorylcholine (MASPCs) were synthesized via a copper-catalyzed 'click' reaction and demonstrated excellent moisture stability. Hydroxylated silicon compounds, silanol, and silica were grafted or modified by MASPCs in the presence of triflic acid (TfOH) and they possessed a good grafting efficiency and high loading rate. (C) 2014 Elsevier Ltd. All rights reserved.
• Development of a reusable colorimetric calcium sensor based on a calix[4]arene-functionalised glass surface
  作者：Yerim Yeon、Bo-Hyeong Kim、Sung Kuk Kim、Sera Lee、Jong Seung Kim、Chul-Ho Jun、Jonathan L. Sessler

  DOI：10.1080/10610278.2012.758369

  日期：2013.2

  A dual functional chromogenic calix[4]arene that contains both hydroxy azophenols and triazoles for colorimetric sensing and cationic recognition, respectively, has been synthesised. This system was further functionalised with dimethallylsilane to permit grafting to a glass surface. This grafting may be used to produce a surface modified glass slides that act as reusable ion-selective colorimetric sensors. UVvis spectral studies revealed that this compound is capable of binding the calcium cation in aqueous media and producing an easily detectable colour change. The same is true for the modified surface set-up. For the free receptor in acetonitrile solution, the absorption maximum undergoes a red shift from 390 to 496 nm upon exposure to calcium cations. In the case of the modified surface, exposure to acetonitrile solution of calcium perchlorate leads to a change in colour from orange to red. Washing with acetone serves to remove the metal cations from the calix[4]arene-functionalised glass and restore the original orange colour. Then the system is ready for reuse. Specifically, following treatment with acetone, the glass may be submerged in a metal solution once again. In the case of exposure to calcium salts, this re-exposure results in a colour change analogous to what was seen for a pristine system. This process may be repeated several times.
• Sc(OTf)3-Mediated Silylation of Hydroxy Functional Groups on a Solid Surface: A Catalytic Grafting Method Operating at Room Temperature
  作者：Ye-Rim Yeon、Young Jun Park、Ji-Sung Lee、Jung-Woo Park、Sin-Gun Kang、Chul-Ho Jun

  DOI：10.1002/anie.200703112

  日期：2008.1