5-Fluor-5-nitro-6-hydroxy-hydro-uracil | 19118-92-4

• 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: 5-Fluor-5-nitro-6-hydroxy-hydro-uracil
• 英文别名: 5-fluoro-6-hydroxy-5-nitro-dihydro-pyrimidine-2,4-dione；5-Fluoro-6-hydroxy-5-nitro-5,6-dihydrouracil；5-fluoro-6-hydroxy-5-nitro-1,3-diazinane-2,4-dione
• CAS: 19118-92-4
• 化学式: C₄H₄FN₃O₅
• 分子量: 193.091
• InChiKey: HDHVNCWYAGPYEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-氟脲嘧啶 在 硫酸 、 硝酸 作用下， 以 水 为溶剂， 以95%的产率得到5-Fluor-5-nitro-6-hydroxy-hydro-uracil
  参考文献：
  名称：

  5-Fluoro-5-halo- and 5-fluoro-5-nitro-substituted uracil derivatives. Synthesis and structure

  摘要：

  5-Bromo-5-fluoro- and 5-chloro-5-fluoro-6-hydroxy-5,6-dihydrouracils were obtained in high yields by oxidative halogenation of 5-fluorouracil. Nitration of 5-fluorouracil gave 5-fluoro-6-hydroxy-5-nitro-5,6-dihydrouracil. Theoretical calculations in B3LYP/6-311+G(d,p) // B3LYP/6-311G(d,p) + IEFPCM approximation and GIAO simulation of C-13 NMR spectra and spin-spin coupling constants agree with the structure of the compounds obtained, which manifest an equatorial orientation of the fluorine atom and an axial orientation of the hydroxy group at position 6 of the dihydrouracil ring. The principal possibility of oxidative iodination of 5-halouracils was studied in B3LYP/CEP-121G approximation. It was found that reversible elimination of iodine by a nucleophilic agent to give the original compounds is the main transformation pathway of the intermediate in this process.

  DOI：

  10.1007/s10593-015-1737-y