9-<(1,3-dibenzoyloxy-2-propoxy)methyl>purine-6-carbonitrile | 171284-42-7

• 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: 9-<(1,3-dibenzoyloxy-2-propoxy)methyl>purine-6-carbonitrile
• CAS: 171284-42-7
• 化学式: C₂₄H₂₃N₅O₃
• 分子量: 429.478
• InChiKey: ICZYAQRIIHAVSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  95.08
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  9-<(1,3-dibenzoyloxy-2-propoxy)methyl>purine-6-carbonitrile 在 palladium dihydroxide ammonium hydroxide 、 环己烯 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 60.0h， 生成 4-amino-8-<(1,3-dihydroxy-2-propoxy)methylamino>pyrimido<5,4-d>pyrimidine
  参考文献：
  名称：

  Synthesis of Certain Acyclic Nucleoside Analogs of 1,2,4-Triazolo[3,4-f][1,2,4]triazine and Pyrimido[5,4-d]pyrimidine

  摘要：

  Synthesis of 2-penten-1-yl (8a) and ganciclovir analog (8b) of 1,2,4-triazolo[3,4-f][1,2,4]triazine was accomplished by the ring annulation of the corresponding hydrazides (6a and 6b), which in turn was obtained by the dehydrative coupling of 4 with 5a or 5b. Base catalysed ring expansion of N9-alkylpurine-6-carbonitriles (10a, 10c, 10e) provided the acyclic analogs of 4-aminopyrimido[5,4-d]pyrimidines (13a, 13d, 13e). Debenzylation of 13e afforded the ganciclovir analog (13f) of 4-amino-8-(beta-D-ribofuranosylamino)pyrimido [5,4-d]pyrimidine. However, compound 10b did not undergo the expected rearrangement but resulted in the formation of the methyl formimidate derivative (12).

  DOI：

  10.1080/15257779508009495
• 作为产物：
  描述：

  1,3-二苄氧基-2-(氯甲氧基)丙烷 、 6-氰嘌呤 在 sodium hydride 作用下， 生成 9-<(1,3-dibenzoyloxy-2-propoxy)methyl>purine-6-carbonitrile
  参考文献：
  名称：

  Synthesis of Certain Acyclic Nucleoside Analogs of 1,2,4-Triazolo[3,4-f][1,2,4]triazine and Pyrimido[5,4-d]pyrimidine

  摘要：

  Synthesis of 2-penten-1-yl (8a) and ganciclovir analog (8b) of 1,2,4-triazolo[3,4-f][1,2,4]triazine was accomplished by the ring annulation of the corresponding hydrazides (6a and 6b), which in turn was obtained by the dehydrative coupling of 4 with 5a or 5b. Base catalysed ring expansion of N9-alkylpurine-6-carbonitriles (10a, 10c, 10e) provided the acyclic analogs of 4-aminopyrimido[5,4-d]pyrimidines (13a, 13d, 13e). Debenzylation of 13e afforded the ganciclovir analog (13f) of 4-amino-8-(beta-D-ribofuranosylamino)pyrimido [5,4-d]pyrimidine. However, compound 10b did not undergo the expected rearrangement but resulted in the formation of the methyl formimidate derivative (12).

  DOI：

  10.1080/15257779508009495