Ethyl 3-[6-[[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]pyridin-2-yl]-3-oxopropanoate | 265114-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 3-[6-[[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]pyridin-2-yl]-3-oxopropanoate
• CAS: 265114-62-3
• 化学式: C₁₇H₂₄N₂O₅
• 分子量: 336.388
• InChiKey: LYBCHHBWAADQRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  85.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 3-[6-[[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]pyridin-2-yl]-3-oxopropanoate 在 aluminum oxide 、 盐酸羟胺 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 6-[(methylamino)methyl]-2-[1-(hydroximino)ethyl]pyridine tris(trifluoroacetate)
  参考文献：
  名称：

  Activation of Oximic Nucleophiles by Coordination of Transition Metal Ions

  摘要：

  A kinetic study of the reactivity in the cleavage of p-nitrophenyl acetate of a series of 2-pyridineoximes, 1-4, and their complexes with Ni-II, Zn-II and Cu-II is reported. Complexation of the oximic ligands leads to a remarkable increase in the acidity of the oximic group, following the order Cu-II > Ni-II > Zn-II. The oximates of free Ligands and their metal complexes, being alpha-nucleophiles, are quite effective in promoting the cleavage of PNPA. However, the reactivity, as defined by the second-order rate constants, is not predictably related to the acidity of the oximic function. The corresponding Bronsted plot shows a linear behaviour up to a pKa value of ca. 8, above which the reactivity of the uncomplexed oximic functions levels off to a limiting value. In the case of the metal ion complexes, a large effect of the Ligand structure on the reactivity was observed. As a consequence, complexes of appropriate ligands and metal ions show a reactivity that exceeds the apparent limiting one of the oximates. The origin of such effects and their possible implications in the development of new reactivators of phosphorylated acetylcholinesterase are discussed.

  DOI：

  10.1002/(sici)1099-0690(200003)2000:6<1045::aid-ejoc1045>3.0.co;2-m
• 作为产物：
  描述：

  6-甲醛-吡啶-2-甲酸乙酯 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 sodium 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 Ethyl 3-[6-[[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]pyridin-2-yl]-3-oxopropanoate
  参考文献：
  名称：

  Activation of Oximic Nucleophiles by Coordination of Transition Metal Ions

  摘要：

  A kinetic study of the reactivity in the cleavage of p-nitrophenyl acetate of a series of 2-pyridineoximes, 1-4, and their complexes with Ni-II, Zn-II and Cu-II is reported. Complexation of the oximic ligands leads to a remarkable increase in the acidity of the oximic group, following the order Cu-II > Ni-II > Zn-II. The oximates of free Ligands and their metal complexes, being alpha-nucleophiles, are quite effective in promoting the cleavage of PNPA. However, the reactivity, as defined by the second-order rate constants, is not predictably related to the acidity of the oximic function. The corresponding Bronsted plot shows a linear behaviour up to a pKa value of ca. 8, above which the reactivity of the uncomplexed oximic functions levels off to a limiting value. In the case of the metal ion complexes, a large effect of the Ligand structure on the reactivity was observed. As a consequence, complexes of appropriate ligands and metal ions show a reactivity that exceeds the apparent limiting one of the oximates. The origin of such effects and their possible implications in the development of new reactivators of phosphorylated acetylcholinesterase are discussed.

  DOI：

  10.1002/(sici)1099-0690(200003)2000:6<1045::aid-ejoc1045>3.0.co;2-m

文献信息

• Activation of Oximic Nucleophiles by Coordination of Transition Metal Ions
  作者：Fabrizio Mancin、Paolo Tecilla、Umberto Tonellato

  DOI：10.1002/(sici)1099-0690(200003)2000:6<1045::aid-ejoc1045>3.0.co;2-m

  日期：2000.3

  A kinetic study of the reactivity in the cleavage of p-nitrophenyl acetate of a series of 2-pyridineoximes, 1-4, and their complexes with Ni-II, Zn-II and Cu-II is reported. Complexation of the oximic ligands leads to a remarkable increase in the acidity of the oximic group, following the order Cu-II > Ni-II > Zn-II. The oximates of free Ligands and their metal complexes, being alpha-nucleophiles, are quite effective in promoting the cleavage of PNPA. However, the reactivity, as defined by the second-order rate constants, is not predictably related to the acidity of the oximic function. The corresponding Bronsted plot shows a linear behaviour up to a pKa value of ca. 8, above which the reactivity of the uncomplexed oximic functions levels off to a limiting value. In the case of the metal ion complexes, a large effect of the Ligand structure on the reactivity was observed. As a consequence, complexes of appropriate ligands and metal ions show a reactivity that exceeds the apparent limiting one of the oximates. The origin of such effects and their possible implications in the development of new reactivators of phosphorylated acetylcholinesterase are discussed.