N-(2-hydroxyethyl)trimethylsilylpropynamide | 444349-08-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-hydroxyethyl)trimethylsilylpropynamide
• 英文别名: N-(2-hydroxyethyl)-3-(trimethylsilyl)prop-2-ynamide；N-(2-hydroxyethyl)-3-(trimethylsilyl)propynamide；N-(2-hydroxyethyl)-3-trimethylsilylprop-2-ynamide
• CAS: 444349-08-0
• 化学式: C₈H₁₅NO₂Si
• 分子量: 185.298
• InChiKey: CADAEZRXBPNDPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.02
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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-hydroxyethyl)trimethylsilylpropynamide 在 4-二甲氨基吡啶 、 甲基磺酰氯 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 以64%的产率得到2-(4,5-Dihydro-1,3-oxazol-2-yl)ethynyl-trimethylsilane
  参考文献：
  名称：

  Synthesis and evaluation of novel heterocyclic MMP inhibitors

  摘要：

  A variety of novel heterocyclic compounds were synthesized and evaluated for MMP inhibition. Broad spectrum inhibition of MMPs 1, 2, 9, and 12 was found with pyridinone-based compounds while N-heterocyclic triazoles and tetrazoles were largely ineffective. A highly selective tetrazole inhibitor for MMP-2 was discovered. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.020
• 作为产物：
  描述：

  3-(三甲基硅基)丙炔酸 、 C.I.酸性橙108 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 12.5h， 以84%的产率得到N-(2-hydroxyethyl)trimethylsilylpropynamide
  参考文献：
  名称：

  Synthesis and evaluation of novel heterocyclic MMP inhibitors

  摘要：

  A variety of novel heterocyclic compounds were synthesized and evaluated for MMP inhibition. Broad spectrum inhibition of MMPs 1, 2, 9, and 12 was found with pyridinone-based compounds while N-heterocyclic triazoles and tetrazoles were largely ineffective. A highly selective tetrazole inhibitor for MMP-2 was discovered. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.020

文献信息

• 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.
• ——
  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.
• Synthesis and evaluation of novel heterocyclic MMP inhibitors
  作者：Ryuji Hayashi、Xiaomin Jin、Gregory R. Cook

  DOI：10.1016/j.bmcl.2007.10.020

  日期：2007.12

  A variety of novel heterocyclic compounds were synthesized and evaluated for MMP inhibition. Broad spectrum inhibition of MMPs 1, 2, 9, and 12 was found with pyridinone-based compounds while N-heterocyclic triazoles and tetrazoles were largely ineffective. A highly selective tetrazole inhibitor for MMP-2 was discovered. (c) 2007 Elsevier Ltd. All rights reserved.