diethyl N-(tert-butyldimethylsilyloxy)aminomethylphosphonate | 208707-22-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl N-(tert-butyldimethylsilyloxy)aminomethylphosphonate
• CAS: 208707-22-6
• 化学式: C₁₁H₂₈NO₄PSi
• 分子量: 297.407
• InChiKey: NFURVYYBCXSYPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  56.79
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diethyl N-(tert-butyldimethylsilyloxy)aminomethylphosphonate 在 氢氟酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 26.5h， 生成
  参考文献：
  名称：

  Heterocyclic Nucleosede Analogues by Cycloaddition Reactions of 1-Vinylthymine with 1,3-Depoles

  摘要：

  1,3-Dipolar cycloaddition of 1-vinylthymine to azides, nitrile oxides, nitrones and nitronates has been investigated as a route to heterocyclic nucleoside analogues in which the nucleoside ribose moiety has been replaced by an alternative heterocycle. Reaction of 1-vinylthymine with highly reactive nitrile oxides affords 1(isoxazolin-5-yl)thymine products in excellent yield at room temperature. The less reactive nitrone dipoles undergo cycloaddition to 1-vinylthymine at elevated temperature to afford 1-(isoxazolidin-5-yl)thymine cycloadducts in good-to-moderate yields, but show a tendency to eliminate thymine from the cycloaddition products over long reaction times. Azide cycloadditions to 1-vinylthymine proceed only under forcing conditions to which the fragile triazoline products are unstable.

  DOI：

  10.1080/07328319808004220
• 作为产物：
  描述：

  O-(叔丁基二甲基硅烷)羟胺 、 甲磺酸,三氟-,(diethoxyphosphinyl)甲基酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到diethyl N-(tert-butyldimethylsilyloxy)aminomethylphosphonate
  参考文献：
  名称：

  Heterocyclic Nucleosede Analogues by Cycloaddition Reactions of 1-Vinylthymine with 1,3-Depoles

  摘要：

  1,3-Dipolar cycloaddition of 1-vinylthymine to azides, nitrile oxides, nitrones and nitronates has been investigated as a route to heterocyclic nucleoside analogues in which the nucleoside ribose moiety has been replaced by an alternative heterocycle. Reaction of 1-vinylthymine with highly reactive nitrile oxides affords 1(isoxazolin-5-yl)thymine products in excellent yield at room temperature. The less reactive nitrone dipoles undergo cycloaddition to 1-vinylthymine at elevated temperature to afford 1-(isoxazolidin-5-yl)thymine cycloadducts in good-to-moderate yields, but show a tendency to eliminate thymine from the cycloaddition products over long reaction times. Azide cycloadditions to 1-vinylthymine proceed only under forcing conditions to which the fragile triazoline products are unstable.

  DOI：

  10.1080/07328319808004220