N-(2-hydroxy-1,1-dimethylethyl)-3-(trimethylsilyl)prop-2-ynamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-hydroxy-1,1-dimethylethyl)-3-(trimethylsilyl)prop-2-ynamide
• 英文别名: N-(2-hydroxy-1,1-dimethylethyl)trimethylsilylpropynamide；N-(2-hydroxy-1,1-dimethylethyl)trimethylsilyl-propynamide；N-(1-hydroxy-2-methylpropan-2-yl)-3-trimethylsilylprop-2-ynamide
• 化学式: C₁₀H₁₉NO₂Si
• 分子量: 213.352
• InChiKey: JRWBYFMSEYTJOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-1,1-dimethylethyl)-3-(trimethylsilyl)prop-2-ynamide 在 KF-Al₂O₃ (5 mol percent) 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以83%的产率得到N-(2-hydroxy-1,1-dimethylethyl)prop-2-ynamide
  参考文献：
  名称：

  Highly efficient desilylation of 3-trimethylsilylprop-2-ynamides by the action of KF-Al2O3

  摘要：

  A highly effective procedure has been developed for desilylation of 3-trimethylsilylprop-2-ynamides in the presence of KF-Al2O3 as catalyst. The corresponding terminal prop-2-ynamides were obtained in high yield in methanol at 25 C using 5 mol % of the catalyst (reaction time 20 min). Rise in temperature leads to the formation of Z, E-3-methoxyprop-2-enamides or 3,3-dimethoxypropanamides as a result of tandem desilylation-addition of methanol, depending on the conditions.

  DOI：

  10.1134/s1070428011120037
• 作为产物：
  描述：

  3-(trimethylsilyl)propynoyl chloride 、 2-氨基-2-甲基-1-丙醇 在 水 作用下， 以 苯 为溶剂， 反应 4.0h， 以88%的产率得到N-(2-hydroxy-1,1-dimethylethyl)-3-(trimethylsilyl)prop-2-ynamide
  参考文献：
  名称：

  摘要：

  A number of previously unknown N-(2-hydroxyethyl)trimethylsilylpropynamides were synthesized by reactions of 2-aminoethyl trimethytsilyl ethers with trimethylsilylpropynoyl chloride. 2-Hydroxyethylamine reacts with trimethylsilylpropynoyl chloride at both nitrogen and oxygen atoms to afford 2-(3-trimethylsilyl-propynoylamino)ethyl trimethylsilylpropynoate.

  DOI：

  10.1023/a:1015334204435

文献信息

• ——
  作者：A. S. Medvedeva、M. V. Andreev、L. P. Safronova、G. I. Sarapulova、D. V. Pavlov、A. V. Afonin

  DOI：10.1023/a:1015334204435

  日期：——

  A number of previously unknown N-(2-hydroxyethyl)trimethylsilylpropynamides were synthesized by reactions of 2-aminoethyl trimethytsilyl ethers with trimethylsilylpropynoyl chloride. 2-Hydroxyethylamine reacts with trimethylsilylpropynoyl chloride at both nitrogen and oxygen atoms to afford 2-(3-trimethylsilyl-propynoylamino)ethyl trimethylsilylpropynoate.
• Highly efficient desilylation of 3-trimethylsilylprop-2-ynamides by the action of KF-Al2O3
  作者：M. V. Andreev、L. P. Safronova、A. S. Medvedeva

  DOI：10.1134/s1070428011120037

  日期：2011.12

  A highly effective procedure has been developed for desilylation of 3-trimethylsilylprop-2-ynamides in the presence of KF-Al2O3 as catalyst. The corresponding terminal prop-2-ynamides were obtained in high yield in methanol at 25 C using 5 mol % of the catalyst (reaction time 20 min). Rise in temperature leads to the formation of Z, E-3-methoxyprop-2-enamides or 3,3-dimethoxypropanamides as a result of tandem desilylation-addition of methanol, depending on the conditions.
• One-Pot Synthesis of 3-(Trimethylsilyl)propynamides
  作者：A. S. Medvedeva、M. V. Andreev、L. P. Safronova

  DOI：10.1134/s1070428010100040

  日期：2010.10

  A highly efficient one-pot procedure was developed for the synthesis of 3-trimethylsilylpropynamides by acylation of amines with trimethylsilylpropynoyl chloride generated in situ. Selective N-acylation and N,O-bis-acylation of -amino alcohols with formation of, respectively, N-(hydroxyalkyl)propynamides and 2-methyl-2-[3-(trimethylsilyl)propynoylamino]propyl 3-(trimethylsilyl)propynoate were accomplished with high yields.