methylphosphonic acid bis(tert-butyldimethylsilyl) ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: methylphosphonic acid bis(tert-butyldimethylsilyl) ester
• 英文别名: Methylphosphonic acid, bis-TBDMS ester；tert-butyl-[[tert-butyl(dimethyl)silyl]oxy-methylphosphoryl]oxy-dimethylsilane
• 化学式: C₁₃H₃₃O₃PSi₂
• 分子量: 324.548
• InChiKey: NZXNCMCIFZVNIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  叔丁基二甲基硅烷醇 、 甲基膦酸 以 正己烷 为溶剂， 反应 2.0h， 以99%的产率得到methylphosphonic acid bis(tert-butyldimethylsilyl) ester
  参考文献：
  名称：

  Direct Reaction of Phosphorus Acids with Hydroxy of a Silanol and on the Silica Gel Surface

  摘要：

  Several phosphorus acids (methyl- and phenylphosphonic, diphenylphosphinic, and ethyl phosphoric acids) were found to give esters on reaction with tert-butyldimethylsilanol. The reactions occurred simply on heating the reactants in an inert solvent (hexane or toluene). The reaction is reversible, and yields of esters were improved by continuous water removal. The dibasic acids gave either mono- or disilyl esters; the latter were more easily purified and characterized. The OH groups on the surface of silica gel were also found to react with various phosphorus acids under similar conditions to give surface-bonded esters. Products were characterized by CP/MAS P-31 and Si-29 NMR. In the case of phenylphosphonic acid and ethyl phosphoric acids, the products were spectrally identical with those obtained by phosphorylation of the surface OH groups with the highly reactive 3-coordinate anhydrides of these acids when generated in the presence of silica gel.

  DOI：

  10.1021/ja00084a014

文献信息

• Direct Reaction of Phosphorus Acids with Hydroxy of a Silanol and on the Silica Gel Surface
  作者：Ivan Lukes、Moheswar Borbaruah、Louis D. Quin

  DOI：10.1021/ja00084a014

  日期：1994.3

  Several phosphorus acids (methyl- and phenylphosphonic, diphenylphosphinic, and ethyl phosphoric acids) were found to give esters on reaction with tert-butyldimethylsilanol. The reactions occurred simply on heating the reactants in an inert solvent (hexane or toluene). The reaction is reversible, and yields of esters were improved by continuous water removal. The dibasic acids gave either mono- or disilyl esters; the latter were more easily purified and characterized. The OH groups on the surface of silica gel were also found to react with various phosphorus acids under similar conditions to give surface-bonded esters. Products were characterized by CP/MAS P-31 and Si-29 NMR. In the case of phenylphosphonic acid and ethyl phosphoric acids, the products were spectrally identical with those obtained by phosphorylation of the surface OH groups with the highly reactive 3-coordinate anhydrides of these acids when generated in the presence of silica gel.