5-Fluoro-6-hydroxy-5,6-dihydrothymine | 55052-48-7

• 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-Fluoro-6-hydroxy-5,6-dihydrothymine
• 英文别名: 5-Fluor-5-methyl-6-hydroxy-5,6-dihydrouracil；5-fluoro-6-hydroxy-5-methyl-dihydro-pyrimidine-2,4-dione；5-fluoro-5-methyl-6-hydroxy-5,6-dihydrouracil；5-Fluoro-6-hydroxy-5-methyl-hexahydro-pyrimidine-2,4-dione；5-fluoro-6-hydroxy-5-methyl-1,3-diazinane-2,4-dione
• CAS: 55052-48-7
• 化学式: C₅H₇FN₂O₃
• 分子量: 162.121
• InChiKey: DMKNPVNFFKEVHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  胸腺嘧啶 以 Ki 、 水 、 fluorine 为溶剂， 生成 5-Fluoro-6-hydroxy-5,6-dihydrothymine
  参考文献：
  名称：

  Process for fluorinating uracil and derivatives thereof

  摘要：

  本文披露了在水溶剂存在的情况下，通过氟气对尿嘧啶及其衍生物进行直接氟化，以产生5-氟尿嘧啶和5-氟尿嘧啶衍生物。该反应产生的新化合物，如5,5-二氟-6-羟基-5,6-二氢尿嘧啶也被披露。5-氟尿嘧啶的衍生物可用作杀菌剂，而5-氟尿嘧啶本身是已知的抗癌化疗药物。

  公开号：

  US03954758A1

文献信息

• A Convenient Synthesis of 5-Fluoropyrimidines Using 1-(Chloromethyl)-4-fluoro-1,4-diazabicyclo[2.cntdot.2.cntdot.2]octane Bis(tetrafluoroborate)-SELECTFLUOR Reagent
  作者：G. Sankar Lal、W. Pastore、R. Pesaresi

  DOI：10.1021/jo00127a046

  日期：1995.11

  The pyrimidine bases uracil and thymine react with the titled reagent in water to generate the corresponding fluorohydrins. Uracil fluorohydrin provides 5-fluorouracil on sublimation. Triacetyluridine reacts similarly in the presence of H2O, AcOH, or MeOH to form the respective adducts from which 5-fluorotriacetyluridine was obtained. The fluorohydrin of diacetylthymidine and the difluoromethoxy derivative of triacetylcytidine were also obtained by reaction of the nucleosides with 1-(chloromethyl)-4-fluoro-1,4-diazobicyclo[2.2.2]octane bis(tetrafluoroborate)-SELECTFLUOR in H2O and MeOH, respectively. This method represents a new practical and direct route to 5-fluoropyrimidine nucleoside.