Diethyl [2-(trimethoxysilyl)ethyl]phosphonate | 20448-87-7

• 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: Diethyl [2-(trimethoxysilyl)ethyl]phosphonate
• 英文别名: 2-diethoxyphosphorylethyl(trimethoxy)silane
• CAS: 20448-87-7
• 化学式: C₉H₂₃O₆PSi
• 分子量: 286.337
• InChiKey: KGDYSXITTOUAPE-UHFFFAOYSA-N

物化性质

• 沸点：
  289.1±13.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  17
• 可旋转键数：
  10
• 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 、 亚磷酸二乙酯 在 偶氮二异丁腈 作用下， 反应 4.0h， 生成 、 Diethyl [2-(trimethoxysilyl)ethyl]phosphonate 、 (2-(dimethyl phosphonato)ethyl)trimethoxysilane
  参考文献：
  名称：

  Intramolecular O → Si donor-acceptor interaction in R2P(=O)CH2CH2SiF3 molecules: Synthesis of dialkyl [2-(trifluorosilyl)ethyl]phosphonate and bis[(chloromethyl)dimethylsilyl] styrylphosphonate

  摘要：

  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.

  DOI：

  10.1134/s1070363206100082

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.