1-((5-((diethoxyphosphorylmethoxy)methyl)-1H-1,2,3-triazol-4-yl)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione | 1426389-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-((5-((diethoxyphosphorylmethoxy)methyl)-1H-1,2,3-triazol-4-yl)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 1-[[5-(diethoxyphosphorylmethoxymethyl)-2H-triazol-4-yl]methyl]-5-methylpyrimidine-2,4-dione
• CAS: 1426389-93-6
• 化学式: C₁₄H₂₂N₅O₆P
• 分子量: 387.332
• InChiKey: DVBGAPLPDRASKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-((5-((diethoxyphosphorylmethoxy)methyl)-1H-1,2,3-triazol-4-yl)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione 在 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 96.0h， 以81%的产率得到1-((5-((ethoxy(hydroxy)phosphorylmethoxy)methyl)-1H-1,2,3-triazol-4-yl)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of novel NH-1,2,3-triazolo-nucleosides by the Banert cascade reaction

  摘要：

  Nucleoside analogs with the 4,5-dimethyl-NH-1,2,3-triazolo-linker between thymine and a carbohydrate, or a hydroxyalkoxyl, or phosphonomethoxyl residue, were obtained by the Bannert cascade reaction from 1-(4-azidobut-2-yn-1-yl)thymine and the carbohydrate or acyclic alcohol. The reaction conditions were developed on the basis of a thermal analysis of the starting azide and by the optimization of the reaction components ratio. The best results were obtained when the reaction cascade employed the azide/nucleophile molar ratio of 1114, at 55 degrees C, with no solvent addition. The reaction showed good discrimination between the pentofuranose hydroxyls, yielding triazoles linked at the carbohydrate 5'-oxygen atom. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.042
• 作为产物：
  描述：

  1-(4-mesyloxybut-2-yn-1-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-((5-((diethoxyphosphorylmethoxy)methyl)-1H-1,2,3-triazol-4-yl)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of novel NH-1,2,3-triazolo-nucleosides by the Banert cascade reaction

  摘要：

  Nucleoside analogs with the 4,5-dimethyl-NH-1,2,3-triazolo-linker between thymine and a carbohydrate, or a hydroxyalkoxyl, or phosphonomethoxyl residue, were obtained by the Bannert cascade reaction from 1-(4-azidobut-2-yn-1-yl)thymine and the carbohydrate or acyclic alcohol. The reaction conditions were developed on the basis of a thermal analysis of the starting azide and by the optimization of the reaction components ratio. The best results were obtained when the reaction cascade employed the azide/nucleophile molar ratio of 1114, at 55 degrees C, with no solvent addition. The reaction showed good discrimination between the pentofuranose hydroxyls, yielding triazoles linked at the carbohydrate 5'-oxygen atom. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.042