1-(2-benzyloxyethyl)-3-methoxypyridin-2(1H)-one | 880098-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-benzyloxyethyl)-3-methoxypyridin-2(1H)-one
• 英文别名: 1-[2-(benzyloxy)ethyl]-3-methoxypyridin-2(1H)-one；3-methoxy-1-(2-phenylmethoxyethyl)pyridin-2-one
• CAS: 880098-46-4
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: IPBYXWWWQABNNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-benzyloxyethyl)-3-methoxypyridin-2(1H)-one 在 palladium on activated charcoal 氢气 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 C₇H₈BBr₂NO₃
  参考文献：
  名称：

  Allosteric Binding of Alkali Metal Ions to a Pseudocryptand Formed by a C-Pivot Tripodal Ligand Containing 3-Hydroxy-2(1H)-pyridinone and Ga(III)

  摘要：

  A novel C-pivot tripodal hexadentate ligand (3,2-HOPOHL) composed of 3-hydroxy-2(1H)-pyridinone as a bidentate ligand, the ethyleneoxy chain as a spacer, and tris(carboxyric acid) as an anchor was synthesized. 3,2-HOPOHL recognized only Na+ ion, suggesting that it pre-organized a cavity due to the electrostatic interaction among the 2(1H)-pyridinone rings. UV-VIS spectroscopic analysis indicated that 3,2-HOPOHL formed a stable intramolecular 1:1 Fe(III) complex in aqueous solution. The stability constant (log K) of 3,2-HOPOHL-Fe(III) complex was estimated to be 27.6 from the competitive reaction with EDTA. H-1-NMR titration of 3,2-HOPOHL-Ga(III) complex with Na+ and K+ ions in CDCl3-CD3CN indicated the formation of 1:1 complexes. The binding constants of Na+- and K+-3,2-HOPOHL-Ga(III) complexes were estimated to be 3.3x10(3) and 7.8x10(3) M-1, respectively, the ion selectivity of K+ toward Na+ being more than two-fold.

  DOI：

  10.3987/com-05-s(k)20
• 作为产物：
  描述：

  3-甲氧基-2(1H)-吡啶酮 、 苄基2-溴乙基醚 在 sodium hydride 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以65%的产率得到1-(2-benzyloxyethyl)-3-methoxypyridin-2(1H)-one
  参考文献：
  名称：

  Allosteric Binding of Alkali Metal Ions to a Pseudocryptand Formed by a C-Pivot Tripodal Ligand Containing 3-Hydroxy-2(1H)-pyridinone and Ga(III)

  摘要：

  A novel C-pivot tripodal hexadentate ligand (3,2-HOPOHL) composed of 3-hydroxy-2(1H)-pyridinone as a bidentate ligand, the ethyleneoxy chain as a spacer, and tris(carboxyric acid) as an anchor was synthesized. 3,2-HOPOHL recognized only Na+ ion, suggesting that it pre-organized a cavity due to the electrostatic interaction among the 2(1H)-pyridinone rings. UV-VIS spectroscopic analysis indicated that 3,2-HOPOHL formed a stable intramolecular 1:1 Fe(III) complex in aqueous solution. The stability constant (log K) of 3,2-HOPOHL-Fe(III) complex was estimated to be 27.6 from the competitive reaction with EDTA. H-1-NMR titration of 3,2-HOPOHL-Ga(III) complex with Na+ and K+ ions in CDCl3-CD3CN indicated the formation of 1:1 complexes. The binding constants of Na+- and K+-3,2-HOPOHL-Ga(III) complexes were estimated to be 3.3x10(3) and 7.8x10(3) M-1, respectively, the ion selectivity of K+ toward Na+ being more than two-fold.

  DOI：

  10.3987/com-05-s(k)20