[4-(6-Amino-purin-9-yl)-1,1-difluoro-butyl]-phosphonic acid diethyl ester | 189556-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: [4-(6-Amino-purin-9-yl)-1,1-difluoro-butyl]-phosphonic acid diethyl ester
• CAS: 189556-58-9
• 化学式: C₁₃H₂₀F₂N₅O₃P
• 分子量: 363.304
• InChiKey: UKKHVKFHTFHNKF-UHFFFAOYSA-N

物化性质

• 沸点：
  517.1±60.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  105.15
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [4-(6-Amino-purin-9-yl)-1,1-difluoro-butyl]-phosphonic acid diethyl ester 在 碘代三甲硅烷 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以80%的产率得到[4-(6-Amino-purin-9-yl)-1,1-difluoro-butyl]-phosphonic acid
  参考文献：
  名称：

  Unsaturated fluoro analogues of adenine nucleotides. Unusual eliminations of hydrogen halides in α,α-difluorophosphonates containing a heterocyclic base

  摘要：

  Reaction of bromodifluoromethyl phosphonate 3 with zinc and propynyl chloride led to allenyl phosphonate which was brominated to give dibromophosphonate 6. Alkylation of adenine 7 with 6 afforded Z- and E-difluorophosphonates 8 and 9. Hydrogenation of 8 furnished saturated difluorophosphonate 10a which was dealkylated to the corresponding phosphonic acid 10b. Reaction of 8 with tetrabutylammonium fluoride gave fluoroenyne phosphonate 11 whereas 9 and 1,5-diazabicyclo[4.3.0] non-5-ene furnished bromofluorodiene phosphonate 16. Hydrogenation of 11 afforded phosphonates 13 and 14 in addition to defluorinated product 15. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00233-0
• 作为产物：
  描述：

  溴氟甲基膦酸二乙酯 在 palladium on activated charcoal 氢气 、 溴 、 potassium carbonate 、 三乙胺 、 copper(I) bromide 、 锌 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、137.9 kPa 条件下， 反应 77.0h， 生成 [4-(6-Amino-purin-9-yl)-1,1-difluoro-butyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Unsaturated fluoro analogues of adenine nucleotides. Unusual eliminations of hydrogen halides in α,α-difluorophosphonates containing a heterocyclic base

  摘要：

  Reaction of bromodifluoromethyl phosphonate 3 with zinc and propynyl chloride led to allenyl phosphonate which was brominated to give dibromophosphonate 6. Alkylation of adenine 7 with 6 afforded Z- and E-difluorophosphonates 8 and 9. Hydrogenation of 8 furnished saturated difluorophosphonate 10a which was dealkylated to the corresponding phosphonic acid 10b. Reaction of 8 with tetrabutylammonium fluoride gave fluoroenyne phosphonate 11 whereas 9 and 1,5-diazabicyclo[4.3.0] non-5-ene furnished bromofluorodiene phosphonate 16. Hydrogenation of 11 afforded phosphonates 13 and 14 in addition to defluorinated product 15. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00233-0

文献信息

• Unsaturated fluoro analogues of adenine nucleotides. Unusual eliminations of hydrogen halides in α,α-difluorophosphonates containing a heterocyclic base
  作者：Ze-Qi Xu、Jiri Zemlicka

  DOI：10.1016/s0040-4020(97)00233-0

  日期：1997.4

  Reaction of bromodifluoromethyl phosphonate 3 with zinc and propynyl chloride led to allenyl phosphonate which was brominated to give dibromophosphonate 6. Alkylation of adenine 7 with 6 afforded Z- and E-difluorophosphonates 8 and 9. Hydrogenation of 8 furnished saturated difluorophosphonate 10a which was dealkylated to the corresponding phosphonic acid 10b. Reaction of 8 with tetrabutylammonium fluoride gave fluoroenyne phosphonate 11 whereas 9 and 1,5-diazabicyclo[4.3.0] non-5-ene furnished bromofluorodiene phosphonate 16. Hydrogenation of 11 afforded phosphonates 13 and 14 in addition to defluorinated product 15. (C) 1997 Elsevier Science Ltd.