tert-butyl N-(5-phenylpyridin-2-yl)-N-prop-2-ynylcarbamate | 1284210-56-5

• 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: tert-butyl N-(5-phenylpyridin-2-yl)-N-prop-2-ynylcarbamate
• CAS: 1284210-56-5
• 化学式: C₁₉H₂₀N₂O₂
• 分子量: 308.38
• InChiKey: KBIUGNGHEHDXFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(5-phenylpyridin-2-yl)-N-prop-2-ynylcarbamate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以59%的产率得到3-methyl-6-phenylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  A Base Promoted Cyclization of N-Propargylaminopyridines. Synthesis of Imidazo[1,2-a]pyridine Derivatives

  摘要：

  A base promoted cyclization of the protected N-propargylaminopyridines was shown to be an efficient method for the preparation of imidazo[1,2-a] pyridine derivatives. The reactions were carried out with a small excess of base, at room temperature or slightly above producing the heterocyclic products in moderate to good yields. The stereoelectronic properties of substituents on the pyridine ring were shown to influence the cyclization process.

  DOI：

  10.1021/ol200508x

文献信息

• Water mediated deprotective intramolecular hydroamination of N-propargylaminopyridines: synthesis of imidazo[1,2-a]pyridines
  作者：Darapaneni Chandra Mohan、Niraj B. Sarang、Subbarayappa Adimurthy

  DOI：10.1016/j.tetlet.2013.08.112

  日期：2013.11

  Metal-free synthesis of substituted imidazole [1,2-alpha]dpyridines from deprotective N-(prop-2-yn-1-yl)pyridin-2-amines in water is elucidated. Electron releasing substituents on pyridine ring provided pure products in quantitative yields without separation by column chromatography. (C) 2013 Elsevier Ltd. All rights reserved.