5-bromo-5-fluoro-6-hydroxy-5,6-dihydrouracil | 1820-76-4

• 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-bromo-5-fluoro-6-hydroxy-5,6-dihydrouracil
• 英文别名: DL-5-Fluor-5-brom-6-hydroxy-hydrouracil；5-Brom-5-fluor-6-hydroxy-5,6-dihydrouracil；5-bromo-5-fluoro-6-hydroxy-dihydro-pyrimidine-2,4-dione；5-Bromo-5-fluoro-6-hydroxy-1,3-diazinane-2,4-dione
• CAS: 1820-76-4
• 化学式: C₄H₄BrFN₂O₃
• 分子量: 226.99
• InChiKey: QINMMEBYOSRGQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 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：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-bromo-5-fluoro-6-hydroxy-5,6-dihydrouracil 在 乙酸酐 作用下， 反应 5.0h， 以40%的产率得到5-氟脲嘧啶
  参考文献：
  名称：

  1-羧甲基-5-甲基尿嘧啶的卤化和硝化。涉及乙酸酐的嗜盐反应

  摘要：

  首次合成了 1-Carboxymethyl-5-halo-6-hydroxy-5-methyl-5,6-dihydrouracils 和 1-carboxymethyl-6-hydroxy-5-methyl-5-mtro-5,6-dihydrouracils 1-羧甲基-5-甲基尿嘧啶的氧化卤化和硝化。二氢尿嘧啶衍生物在 C(5) 位置带有一个 Br 原子，在 C(6) 位置带有一个羟基，经过 Ac2O 处理后会发生脱氧卤化。

  DOI：

  10.1007/s11172-020-3015-0
• 作为产物：
  描述：

  5-氟脲嘧啶 在 硫酸 、 双氧水 、 potassium bromide 作用下， 以 水 为溶剂， 以95%的产率得到5-bromo-5-fluoro-6-hydroxy-5,6-dihydrouracil
  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

文献信息

• 5-Fluoro-5-halo- and 5-fluoro-5-nitro-substituted uracil derivatives. Synthesis and structure
  作者：Inna B. Chernikova、Sergey L. Khursan、Leonid V. Spirikhin、Marat S. Yunusov

  DOI：10.1007/s10593-015-1737-y

  日期：2015.6

  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.
• Halogenation and nitration of 1-carboxymethyl-5-methyluracil. Halophilic reaction involving acetic anhydride
  作者：I. B. Chernikova、M. S. Yunusov

  DOI：10.1007/s11172-020-3015-0

  日期：2020.11

  1-Carboxymethyl-5-halo-6-hydroxy-5-methyl-5,6-dihydrouracils and 1-carboxymethyl-6-hydroxy-5-methyl-5-mtro-5,6-dihydrouracils were synthesized for the first time by oxidative halogenation and nitration of 1-carboxymethyl-5-methyluracil. Dihydrouracil derivatives bearing a Br atom at position C(5) and a hydroxy group at position C(6) treated with Ac2O undergo deoxyhalogenation.

  首次合成了 1-Carboxymethyl-5-halo-6-hydroxy-5-methyl-5,6-dihydrouracils 和 1-carboxymethyl-6-hydroxy-5-methyl-5-mtro-5,6-dihydrouracils 1-羧甲基-5-甲基尿嘧啶的氧化卤化和硝化。二氢尿嘧啶衍生物在 C(5) 位置带有一个 Br 原子，在 C(6) 位置带有一个羟基，经过 Ac2O 处理后会发生脱氧卤化。