1-(pyridin-2-ylamino)-3-trimethylsilylprop-2-yn-1-ol | 1025068-34-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(pyridin-2-ylamino)-3-trimethylsilylprop-2-yn-1-ol
• 英文别名: 1-(Pyridin-2-ylamino)-3-trimethylsilyl-prop-2-yn-1-ol
• CAS: 1025068-34-1
• 化学式: C₁₁H₁₆N₂OSi
• 分子量: 220.346
• InChiKey: WMHVVFXHWOPVCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 3-三甲基甲硅烷基丙炔醛 以 水 、 乙腈 为溶剂， 以51%的产率得到N-(3-trimethylsilylprop-2-yn-1-ylidene)pyridin-2-amine
  参考文献：
  名称：

  10.1007/s11178-008-1020-0

  摘要：

  DOI：

  10.1007/s11178-008-1020-0

文献信息

• Tentative mechanisms of 1,2-dihydropyridine and 4H-pyran formation via the reaction of 3-trimethylsilyl-2-propyn-1-al with 2-aminopyridine and water: experimental and quantum chemistry studies
  作者：Vladimir A. Shagun、Alevtina S. Medvedeva、Alexander V. Mareev

  DOI：10.1016/j.tet.2012.12.056

  日期：2013.3

  The reaction of N-(2-pyridyl)-2-(trimethylsilylethynyl)-1,2-dihydropyridine-3,5-dicarbaldehyde self-assembling from three molecules of 3-trimethylsilyl-2-propyn-1-al and one molecule of 2-aminopyridine was monitored by H-1 NMR spectroscopy. It was shown that the aldehyde and amine ratio affects the concurrent trimerization of 3-trimethylsilyl-2-propyn-1-al into 4-(trimethylsilylethynyl)-4H-pyran-3,5-dicarbaldehyde involving one molecule of water as a nucleophile. Two plausible mechanisms of 1,2dihydropyridine and 4H-pyran cascade assembling are proposed and analyzed by quantum chemical methods (MP2 and B3LYP). The transition states were found and the activation barriers were calculated for the key steps of the reactions. The potential energy surface (PES) analysis performed do suggests an alternative radical mechanism leading to 1,2-dihydropyridine and 4H-pyran with significantly lower (by 10 kcal/mol) activation barriers at the limiting stages. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.