6-(N-propylamino)-9-(β-D-ribofuranosyl)-2,3-dihydropurin-2-one | 23541-27-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-(N-propylamino)-9-(β-D-ribofuranosyl)-2,3-dihydropurin-2-one
• 英文别名: 9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-(propylamino)-1H-purin-2(9H)-one；9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(propylamino)-1H-purin-2-one
• CAS: 23541-27-7
• 化学式: C₁₃H₁₉N₅O₅
• 分子量: 325.324
• InChiKey: JXGJQLCFRFEZOC-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  139
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  正丙胺 、 6-氯-9-(2,3,5-三-O-乙酰基呋喃戊糖基)-1,9-二氢-2H-嘌呤-2-酮 反应 2.5h， 以91%的产率得到6-(N-propylamino)-9-(β-D-ribofuranosyl)-2,3-dihydropurin-2-one
  参考文献：
  名称：

  6-Chloroxanthosine, a Useful Intermediate for the Efficient Syntheses of [6-¹⁵N]-Isoguanosine, Isoinosine and Other Purine Nucleoside Analogues

  摘要：

  6-Chloroxanthosine 1, when activated towards nucleophilic displacement at the 6-C position by conversion into the corresponding 3-N-(2,4-dinitrophenyl) derivative 4, reacted with aq. (NH3)-N-15 to afford [6-N-15]-isoguanosine 3b in 81% overall yield. Catalytic hydrogenation (Pd/C) of 1 led in 60% yield to isoinosine 8; alternatively, this could be obtained in 88% overall yield through alkaline hydrolysis of triphenylphosphonium salt 6, synthesized from 1 by reaction with PPh(3). The reactivity of 1 was further explored by treating it with primary and secondary amines: the 6-N propylamino and the 6-N piperidinyl derivatives (5a and 5b, respectively) could thus both be prepared in more than 90% yield.

  DOI：

  10.1080/07328319708002532