1-(2-(2-(pyridin-2-yloxy)ethoxy)ethyl)piperazine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-(2-(pyridin-2-yloxy)ethoxy)ethyl)piperazine
• 英文别名: 1-[2-(2-Pyridin-2-yloxyethoxy)ethyl]piperazine；1-[2-(2-pyridin-2-yloxyethoxy)ethyl]piperazine
• 化学式: C₁₃H₂₁N₃O₂
• 分子量: 251.329
• InChiKey: BMUWHCLENHURSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-碘吡啶 、 1-[2-(2-羟基乙氧基)乙基]哌嗪 在 copper(l) iodide 3,4,7,8-四甲基-1,10-菲罗啉 、 3 A molecular sieve 、 caesium carbonate 作用下， 反应 20.0h， 以82%的产率得到1-(2-(2-(pyridin-2-yloxy)ethoxy)ethyl)piperazine
  参考文献：
  名称：

  N- versus O-Arylation of Aminoalcohols:  Orthogonal Selectivity in Copper-Based Catalysts

  摘要：

  Two complementary protocols for copper-catalyzed arylation of aminoalcohols were developed. Selective N-arylation was accomplished at room temperature using 2-isobutyrylcyclohexanone (a beta-diketone) as supporting ligand, while selective O-arylation required the use of 3,4,7,8-tetramethylphenanthroline at 80-110 degrees C. Systematic examination of the reaction scope revealed that high levels of selectivity are achieved for a variety of substrates, provided that nonchelating (or weakly chelating) aminoalcohols are used. The generality of the method was highlighted by the synthesis, in a pairwise fashion, of a number of functionalized N- and O-arylated aminoalcohols.

  DOI：

  10.1021/ja068926f

文献信息

• N- versus O-Arylation of Aminoalcohols:  Orthogonal Selectivity in Copper-Based Catalysts
  作者：Alexandr Shafir、Phillip A. Lichtor、Stephen L. Buchwald

  DOI：10.1021/ja068926f

  日期：2007.3.1

  Two complementary protocols for copper-catalyzed arylation of aminoalcohols were developed. Selective N-arylation was accomplished at room temperature using 2-isobutyrylcyclohexanone (a beta-diketone) as supporting ligand, while selective O-arylation required the use of 3,4,7,8-tetramethylphenanthroline at 80-110 degrees C. Systematic examination of the reaction scope revealed that high levels of selectivity are achieved for a variety of substrates, provided that nonchelating (or weakly chelating) aminoalcohols are used. The generality of the method was highlighted by the synthesis, in a pairwise fashion, of a number of functionalized N- and O-arylated aminoalcohols.