[(Z)-4-(6-Amino-purin-9-yl)-3-bromo-1,1-difluoro-but-2-enyl]-phosphonic acid diethyl ester | 189556-56-7

• 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: [(Z)-4-(6-Amino-purin-9-yl)-3-bromo-1,1-difluoro-but-2-enyl]-phosphonic acid diethyl ester
• 英文别名: 9-[(Z)-2-bromo-4-diethoxyphosphoryl-4,4-difluorobut-2-enyl]purin-6-amine
• CAS: 189556-56-7
• 化学式: C₁₃H₁₇BrF₂N₅O₃P
• 分子量: 440.184
• InChiKey: TXGRMBWMGAZJPG-UITAMQMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(Z)-4-(6-Amino-purin-9-yl)-3-bromo-1,1-difluoro-but-2-enyl]-phosphonic acid diethyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以49%的产率得到9-[(Z)-4-diethoxyphosphoryl-1-fluorobut-1-en-3-ynyl]purin-6-amine
  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 溴 、 potassium carbonate 、 copper(I) bromide 、 锌 作用下， 反应 75.0h， 生成 [(Z)-4-(6-Amino-purin-9-yl)-3-bromo-1,1-difluoro-but-2-enyl]-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.