1-(6-hydroxypyridin-3-yl)-1H-pyridin-2-one | 850495-93-1

• 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-(6-hydroxypyridin-3-yl)-1H-pyridin-2-one
• 英文别名: 1-(6-oxo-1H-pyridin-3-yl)pyridin-2-one
• CAS: 850495-93-1
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: ZSEMHEGKTWBJAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-叔丁氧基-5-溴吡啶 、 1-(6-hydroxypyridin-3-yl)-1H-pyridin-2-one 在 copper(l) iodide 、 potassium carbonate 、 (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以82%的产率得到1-(1-(6-tert-butoxypyridin-3-yl)-1,6-dihydro-6-oxopyridin-3-yl)-1H-pyridin-2-one
  参考文献：
  名称：

  An improved Ullmann–Ukita–Buchwald–Li conditions for CuI-catalyzed coupling reaction of 2-pyridones with aryl halides

  摘要：

  An effective CuI-trans-N,N'-dimethylcyclohexane-1,2-diamine (DMCDA)-K2CO3-cataIyzed coupling reaction of 2-pyridones with aryl halides is described. Under our conditions, DMCDA was found to be an effective catalyst that facilitates the coupling reactions even in toluene, a common industrial solvent. In addition, 3-bromopyridine could also be coupled effectively under these conditions, indicating that the catalytic reactivity of this system is high. The reaction could be applied for polymer modification and iterative oligo-pyridone synthesis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.063
• 作为产物：
  描述：

  1-(6-tert-butoxypyridin-3-yl)-1H-pyridin-2-one 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到1-(6-hydroxypyridin-3-yl)-1H-pyridin-2-one
  参考文献：
  名称：

  An improved Ullmann–Ukita–Buchwald–Li conditions for CuI-catalyzed coupling reaction of 2-pyridones with aryl halides

  摘要：

  An effective CuI-trans-N,N'-dimethylcyclohexane-1,2-diamine (DMCDA)-K2CO3-cataIyzed coupling reaction of 2-pyridones with aryl halides is described. Under our conditions, DMCDA was found to be an effective catalyst that facilitates the coupling reactions even in toluene, a common industrial solvent. In addition, 3-bromopyridine could also be coupled effectively under these conditions, indicating that the catalytic reactivity of this system is high. The reaction could be applied for polymer modification and iterative oligo-pyridone synthesis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.063

文献信息

• Oligopyridones: preparation and their folding behavior in polar aprotic solvents
  作者：Chih-Kai Liang、Po-Shih Wang、Man-kit Leung

  DOI：10.1016/j.tet.2008.12.024

  日期：2009.2

  The oligomerization of 5-bromo-2-hydroxypyridine through a CuI catalyzed one-pot condensation tactics was developed. A series of oligopyridones, from dipyridione to penta-pyridone, were therefore synthesized via the CuI-promoted C–N coupling reactions. The oligopyridones favor to have folded conformations in polar aprotic solvents. These were confirmed by using 1H NMR, NOESY, and 1D-NOE experiments

  通过CuI催化的一锅缩合策略，开发了5-溴-2-羟基吡啶的低聚反应。因此，通过CuI促进的C–N偶联反应合成了从吡啶酮到五吡啶酮的一系列低聚吡啶酮。寡吡啶酮倾向于在极性非质子溶剂中具有折叠构象。这些通过使用1 H NMR，NOESY和1D-NOE实验得到证实。
• An improved Ullmann–Ukita–Buchwald–Li conditions for CuI-catalyzed coupling reaction of 2-pyridones with aryl halides
  作者：Po-Shih Wang、Chih-Kai Liang、Man-kit Leung

  DOI：10.1016/j.tet.2005.01.063

  日期：2005.3

  An effective CuI-trans-N,N'-dimethylcyclohexane-1,2-diamine (DMCDA)-K2CO3-cataIyzed coupling reaction of 2-pyridones with aryl halides is described. Under our conditions, DMCDA was found to be an effective catalyst that facilitates the coupling reactions even in toluene, a common industrial solvent. In addition, 3-bromopyridine could also be coupled effectively under these conditions, indicating that the catalytic reactivity of this system is high. The reaction could be applied for polymer modification and iterative oligo-pyridone synthesis. (c) 2005 Elsevier Ltd. All rights reserved.