9--6-(4-chlorophenylsulfanyl)-2-(phenylacetamido)-9H-purine | 172324-62-8

• 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--6-(4-chlorophenylsulfanyl)-2-(phenylacetamido)-9H-purine
• CAS: 172324-62-8
• 化学式: C₃₁H₂₈ClN₅O₂S
• 分子量: 570.115
• InChiKey: GMWJMZIEZHFVER-GUOBSTCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  81.93
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  9--6-(4-chlorophenylsulfanyl)-2-(phenylacetamido)-9H-purine 在 1,1,2,3-四甲基胍 、 三氯化硼 、 二乙酰一肟 、 间氯过氧苯甲酸 、 甲胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 9.08h， 生成 2-amino-9-[3-(hydroxymethyl)cyclobutyl]-3H-purin-6-one
  参考文献：
  名称：

  Synthesis of 9-[cis-3-(hydroxymethyl)cyclobutyl]-adenine and -guanine

  摘要：

  2,2-Dichloro-3-(benzyloxymethyl)cyclobutanone 15, which was prepared in 50% yield by the cycloaddition of dichloroketene to allyl benzyl ether 14, was converted in four steps and in similar to 40% overall yield into trans-3-(benzyloxymethyl)cyclobutanol 11b. The latter alcohol 11b was coupled under Mitsunobu conditions with 6-(4-chlorophenylsulfanyl)-9H-purine 21b and 6-(4-chlorophenylsulfanyl)-2-(phenylacetamido)-9H-purine 21c to give the 9-cyclobutylpurine derivatives 22 and 24, respectively, in 88 and 60% yield. The former product 22 was converted in three steps and in 39% overall yield into 9-[cis-3-(hydroxymethyl)cyclobutyl]adenine 6, and the latter product was converted in four steps and in 42% overall yield into 9-[cis-3-(hydroxymethyl)cyclobutyl] guanine 7. X-Ray crystallographic data relating to compounds 22 and 24 are also reported.

  DOI：

  10.1039/p19950002281
• 作为产物：
  描述：

  2-amino-6-(4-chlorophenylsulfanyl)-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine 在 2,6-二甲基吡啶 、 三氟化硼乙醚 、 三苯基膦 、 偶氮二甲酸二乙酯 、 苯酚 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 34.0h， 生成 9--6-(4-chlorophenylsulfanyl)-2-(phenylacetamido)-9H-purine
  参考文献：
  名称：

  Synthesis of 9-[cis-3-(hydroxymethyl)cyclobutyl]-adenine and -guanine

  摘要：

  2,2-Dichloro-3-(benzyloxymethyl)cyclobutanone 15, which was prepared in 50% yield by the cycloaddition of dichloroketene to allyl benzyl ether 14, was converted in four steps and in similar to 40% overall yield into trans-3-(benzyloxymethyl)cyclobutanol 11b. The latter alcohol 11b was coupled under Mitsunobu conditions with 6-(4-chlorophenylsulfanyl)-9H-purine 21b and 6-(4-chlorophenylsulfanyl)-2-(phenylacetamido)-9H-purine 21c to give the 9-cyclobutylpurine derivatives 22 and 24, respectively, in 88 and 60% yield. The former product 22 was converted in three steps and in 39% overall yield into 9-[cis-3-(hydroxymethyl)cyclobutyl]adenine 6, and the latter product was converted in four steps and in 42% overall yield into 9-[cis-3-(hydroxymethyl)cyclobutyl] guanine 7. X-Ray crystallographic data relating to compounds 22 and 24 are also reported.

  DOI：

  10.1039/p19950002281