diethyl (2-methoxy-4-pyridinylmethyl)phosphonate | 184957-19-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl (2-methoxy-4-pyridinylmethyl)phosphonate
• 英文别名: Diethyl [(2-methoxypyridin-4-yl)methyl]phosphonate；4-(diethoxyphosphorylmethyl)-2-methoxypyridine
• CAS: 184957-19-5
• 化学式: C₁₁H₁₈NO₄P
• 分子量: 259.242
• InChiKey: KKJRJYOKVHEOKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  369.9±32.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (吡啶-4-甲基)磷酸二乙酯 在 间氯过氧苯甲酸 、 硫酸二甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 70.0h， 生成 diethyl (2-methoxy-4-pyridinylmethyl)phosphonate
  参考文献：
  名称：

  Synthesis of 14C-labelled CGS 19755, a selective NMDA antagonist

  摘要：

  CGS 19755 is a selective NMDA (N-methyl-D-aspartate) antagonist presently under development as a neuronal protecting agent after stroke and head trauma. It was synthesized with C-14-labelling in the carboxylic acid side chain via the synthetic route displayed in Scheme 1. Key steps in the synthesis involved a Reissert-Henze addition of potassium [C-14]cyanide to a functionalized pyridine N-oxide, followed by hydrolysis and a selective hydrogenation affording the desired cis-substituted piperidine target. Using this procedure, [C-14]CGS 19755 was prepared with radiochemical purity of 99.6%. The synthesis demonstrates the utility of the Reissert-Henze reaction, in conjunction with palladium/rhodium-catalyzed hydrogenation, as a facile means of preparing C-14-labelled cis-2,4-substituted cyclic amino acids.

  DOI：

  10.1002/(sici)1099-1344(199611)38:11<989::aid-jlcr922>3.0.co;2-m

文献信息

• Synthesis of 14C-labelled CGS 19755, a selective NMDA antagonist
  作者：Alban J. Allentoff、Mahesh Desai、Bohdan Markus、Timothy Duelfer

  DOI：10.1002/(sici)1099-1344(199611)38:11<989::aid-jlcr922>3.0.co;2-m

  日期：1996.11

  CGS 19755 is a selective NMDA (N-methyl-D-aspartate) antagonist presently under development as a neuronal protecting agent after stroke and head trauma. It was synthesized with C-14-labelling in the carboxylic acid side chain via the synthetic route displayed in Scheme 1. Key steps in the synthesis involved a Reissert-Henze addition of potassium [C-14]cyanide to a functionalized pyridine N-oxide, followed by hydrolysis and a selective hydrogenation affording the desired cis-substituted piperidine target. Using this procedure, [C-14]CGS 19755 was prepared with radiochemical purity of 99.6%. The synthesis demonstrates the utility of the Reissert-Henze reaction, in conjunction with palladium/rhodium-catalyzed hydrogenation, as a facile means of preparing C-14-labelled cis-2,4-substituted cyclic amino acids.