3-ethoxycarbonyl-5-<<<2-(diethylphosphono)methoxy>ethoxy>methyl>pyridine | 219687-34-0

• 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: 3-ethoxycarbonyl-5-<<<2-(diethylphosphono)methoxy>ethoxy>methyl>pyridine
• 英文别名: Ethyl 5-[2-[[diethoxy(oxido)phosphaniumyl]methoxy]ethoxymethyl]pyridine-3-carboxylate
• CAS: 219687-34-0
• 化学式: C₁₆H₂₆NO₇P
• 分子量: 375.359
• InChiKey: VEIYJFGKSZDLQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-ethoxycarbonyl-5-<<<2-(diethylphosphono)methoxy>ethoxy>methyl>pyridine 在 三甲基溴硅烷 、 氨 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 生成 3-carbamoyl-5-<<2-(phosphonomethoxy)ethoxy>methyl>pyridine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Phosphonate Derivatives of Some Acyclic Pyridine-C-Nucleosides

  摘要：

  The synthesis of phosphonomethoxy derivatives of some acyclic pyridine-C-nucleosides is described. Reaction of the acyclic nucleoside alkoxides with diethyl (tosyloxymethyl)phosphonate (5) led to the protected phosphonate derivatives. After eventual modification of the pyridine moiety, the ethyl protecting groups could be removed by treatment with bromotrimethylsilane. The phosphonates were evaluated against a series of tumor cell lines and a variety of viruses. Compared to the nucleoside analogues, they showed a slightly higher activity.

  DOI：

  10.1080/07328319808004329
• 作为产物：
  描述：

  对甲苯磺酰氧甲基膦酸二乙酯 、 5-(2-hydroxyethoxymethyl)-3-methoxycarbonylpyridine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以20%的产率得到3-ethoxycarbonyl-5-<<<2-(diethylphosphono)methoxy>ethoxy>methyl>pyridine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Phosphonate Derivatives of Some Acyclic Pyridine-C-Nucleosides

  摘要：

  The synthesis of phosphonomethoxy derivatives of some acyclic pyridine-C-nucleosides is described. Reaction of the acyclic nucleoside alkoxides with diethyl (tosyloxymethyl)phosphonate (5) led to the protected phosphonate derivatives. After eventual modification of the pyridine moiety, the ethyl protecting groups could be removed by treatment with bromotrimethylsilane. The phosphonates were evaluated against a series of tumor cell lines and a variety of viruses. Compared to the nucleoside analogues, they showed a slightly higher activity.

  DOI：

  10.1080/07328319808004329