1-(6-azidohexyl)-3,6-dimethyluracil | 1374434-61-3

• 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-(6-azidohexyl)-3,6-dimethyluracil
• 英文别名: 1-(6-azidohexyl)-3,6-dimethylpyrimidine-2,4-dione
• CAS: 1374434-61-3
• 化学式: C₁₂H₁₉N₅O₂
• 分子量: 265.315
• InChiKey: OHOZVBXKPJWOLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(6-azidohexyl)-3,6-dimethyluracil 、 2-丙炔-1-醇 在 copper(II) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 以91%的产率得到1-[6-(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)hexyl]-3,6-dimethyluracil
  参考文献：
  名称：

  1,3-dipolar cycloaddition reactions in the series of N-alkynyl-substituted uracils

  摘要：

  Reactions of 1-(omega-bromoalkyl)-3,6-dimethyluracils and 1,3-bis(omega-bromoalkyl)-6-methyluracils with sodium azide gave the corresponding mono- and bis-azides. 1,3-Dipolar cycloaddition of the latter with prop-2-yn-1-ol, hex-1-yne, and dec-1-yne in the presence of copper(I) ions afforded acyclic and macrocyclic uracil derivatives containing 1,4-disubstituted 1,2,3-triazole fragments, which were subjected to quaternization with propyl iodide and methyl p-toluenesulfonate at the 1,2,3-triazole nitrogen atom.

  DOI：

  10.1134/s1070428012040203
• 作为产物：
  描述：

  1-(6-bromohex-1-y)-3,6-dimethyluracil 在 sodium azide 、 四丁基硫酸氢铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以100%的产率得到1-(6-azidohexyl)-3,6-dimethyluracil
  参考文献：
  名称：

  1,3-dipolar cycloaddition reactions in the series of N-alkynyl-substituted uracils

  摘要：

  Reactions of 1-(omega-bromoalkyl)-3,6-dimethyluracils and 1,3-bis(omega-bromoalkyl)-6-methyluracils with sodium azide gave the corresponding mono- and bis-azides. 1,3-Dipolar cycloaddition of the latter with prop-2-yn-1-ol, hex-1-yne, and dec-1-yne in the presence of copper(I) ions afforded acyclic and macrocyclic uracil derivatives containing 1,4-disubstituted 1,2,3-triazole fragments, which were subjected to quaternization with propyl iodide and methyl p-toluenesulfonate at the 1,2,3-triazole nitrogen atom.

  DOI：

  10.1134/s1070428012040203

文献信息

• Conjugates of nucleobases with triazole-hydroxamic acids for the reactivation of acetylcholinesterase and treatment of delayed neurodegeneration induced by organophosphate poisoning
  作者：Marina M. Shulaeva、Irina V. Zueva、Anton E. Nikolaev、Liliya F. Saifina、Dilyara R. Sharafutdinova、Vasily M. Babaev、Vyacheslav E. Semenov、Konstantin A. Petrov

  DOI：10.1016/j.bioorg.2023.106858

  日期：2023.12