(2-(dimethyl phosphonato)ethyl)trimethoxysilane | 20728-21-6

• 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: (2-(dimethyl phosphonato)ethyl)trimethoxysilane
• 英文别名: DMPTMS；2-Dimethoxyphosphorylethyl(trimethoxy)silane
• CAS: 20728-21-6
• 化学式: C₇H₁₉O₆PSi
• 分子量: 258.284
• InChiKey: KTBDNSOWRGZLJK-UHFFFAOYSA-N

物化性质

• 沸点：
  252.5±13.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙烯基三甲氧基硅烷 、 亚磷酸二甲酯 在 二叔丁基过氧化物 作用下， 反应 17.0h， 以60%的产率得到(2-(dimethyl phosphonato)ethyl)trimethoxysilane
  参考文献：
  名称：

  Large pore raspberry textured phosphonate@silica nanoparticles for protein immobilization

  摘要：

  本文报道了具有大孔（11 nm）单分散覆盆子状结构膦酸盐@二氧化硅纳米粒子（70-90 nm）的合成，该纳米粒子具有高蛋白质固定化容量。覆盆子状纳米粒子用RNP_PME(2.5)表示，膦酸盐负载量为2.5 mmol g-1，使用有机硅膦酸盐（MeO）3SiCH2CH2PO（OMe）2作为二氧化硅表面修饰剂和结构导向剂。RNP_PME(2.5)的形成需要特定的反应条件，包括膦酸盐、碱、表面活性剂和共溶剂的温度和浓度。罗丹明B标记的RNP_PME(2.5)很容易被HeLa细胞内化，且不影响细胞活力。RNP_PME(2.5)的水分散体在几个月内保持稳定。在蛋白质固定化研究中，使用BSA（牛血清白蛋白）与RNP_PME(2.5)、小孔（约3 nm）膦酸盐@二氧化硅纳米粒子NP_PME(1.0)和NP_PME(0.2)以及介孔二氧化硅纳米粒子MSN，大孔RNP_PME(2.5)的BSA负载量最高，为266 mg g-1，形成最稳定的水

  DOI：

  10.1039/c3tb21263g

文献信息

• Intramolecular O → Si donor-acceptor interaction in R2P(=O)CH2CH2SiF3 molecules: Synthesis of dialkyl [2-(trifluorosilyl)ethyl]phosphonate and bis[(chloromethyl)dimethylsilyl] styrylphosphonate
  作者：M. G. Voronkov、V. A. Pestunovich、N. F. Chernov、A. I. Albanov、E. F. Belogolova、L. V. Klyba、A. E. Pestunovich

  DOI：10.1134/s1070363206100082

  日期：2006.10

  The reaction of diethyl [2-(triethoxysilyl)ethyl]phosphonate with boron trifluoride etherate was used to synthesize diethyl [2-(trifluorosilyl)ethyl]phosphonate. The reaction of bis(trimethylsilyl) styrylphosphonate with chloro(chloromethyl)dimethylsilane gave bis [(chloromethyl)dimethylsilyl] styrylphosphonate. Multinuclear H-1, C-13, F-19, Si-29, and P-31 N MR spectroscopy established the absence of a O -> Si coordination bond in these compounds and the four-coordinate state of the silicon atom. Evidence for this finding was obtained by B3LYP/6-31G(d) quantum-chemical calculations. However, the same calculations for R2P(=O)center dot CH2CH2SiF3 (R = Me, Me2N) showed the presence in such molecules of an O -> Si coordination bond both in the gas phase and in CHO solution. The distance between the O and Si atoms in this series molecules decreases with R in the order: MeO > Me > MeN. The axial Si-F bond length increases in the same order and parallels the order of the Hammet sigma(0)(m) constants of these substituents, relating to their interaction with pi-electron systems.
• New phosphonic acid polysilsesquioxane mild solid acid catalysts
  作者：Majda Sebah、Sai P. Maddala、Peter Haycock、Alice Sullivan、Harold Toms、John Wilson

  DOI：10.1016/j.molcata.2013.03.021

  日期：2013.8

  A simple easily scalable one-pot route to new phosphonic acid polysilsesquioxanes, PAPSQ, [(O3/2SiCH2R)(x)(O3/2SiCHR(CH2)(2)SiO3/2)(y)](n) where R = CH2PO3H2, is described in this paper. Nuclear magnetic resonance (NMR), electron microscopy (SEM), thermogravimetric analysis, nitrogen sorption porosimetry, phosphorus and available acid analysis were used to characterise the new PAPSQ materials. The materials were shown to be very efficient and recyclable mild solid acid catalysts for organic transformations including those relevant to biomass conversion such as esterification, transesterification and dehydration of fructose to the important intermediate 5-hydroxymethylfurfural. (C) 2013 Elsevier B.V. All rights reserved.
• Large pore raspberry textured phosphonate@silica nanoparticles for protein immobilization
  作者：Sai Prakash Maddala、Diana Velluto、Zofia Luklinska、Alice C. Sullivan

  DOI：10.1039/c3tb21263g

  日期：——

  This paper reports the synthesis of large pore (11 nm) monodisperse raspberry textured phosphonate@silica nanoparticles (70–90 nm) with high capacity for protein immobilization. The raspberry nanoparticles denoted RNP_PME(2.5) with phosphonate loading 2.5 mmol g−1, formed using an organosilanephosphonate (MeO)3SiCH2CH2PO(OMe)2, as silica surface modifier and structure directing agent. Specific reaction conditions including temperature and concentration of phosphonate, base, surfactant and co-solvent were required for RNP_PME(2.5) formation. Rhodamine B labelled RNP_PME(2.5) was readily internalised by HeLa cells with no deficit of cell viability. Aqueous dispersions of RNP_PME(2.5) were stable over several months. In protein immobilization studies using BSA, bovine serum albumin, with RNP_PME(2.5), smaller pore (∼3 nm) phosphonate@silica nanoparticles NP_PME(1.0) and NP_PME(0.2) and mesoporous silica nanoparticles, MSN, the large pore RNP_PME(2.5) gave highest BSA loading 266 mg g−1, formed the most stable aqueous dispersions (BSA@MSN was unstable and precipitated) and gave the best protection against BSA structural distortion at pH 7.4.

  本文报道了具有大孔（11 nm）单分散覆盆子状结构膦酸盐@二氧化硅纳米粒子（70-90 nm）的合成，该纳米粒子具有高蛋白质固定化容量。覆盆子状纳米粒子用RNP_PME(2.5)表示，膦酸盐负载量为2.5 mmol g-1，使用有机硅膦酸盐（MeO）3SiCH2CH2PO（OMe）2作为二氧化硅表面修饰剂和结构导向剂。RNP_PME(2.5)的形成需要特定的反应条件，包括膦酸盐、碱、表面活性剂和共溶剂的温度和浓度。罗丹明B标记的RNP_PME(2.5)很容易被HeLa细胞内化，且不影响细胞活力。RNP_PME(2.5)的水分散体在几个月内保持稳定。在蛋白质固定化研究中，使用BSA（牛血清白蛋白）与RNP_PME(2.5)、小孔（约3 nm）膦酸盐@二氧化硅纳米粒子NP_PME(1.0)和NP_PME(0.2)以及介孔二氧化硅纳米粒子MSN，大孔RNP_PME(2.5)的BSA负载量最高，为266 mg g-1，形成最稳定的水