2-[(7H-purin-6-ylamino)methylidene]propanedial

• 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: 2-[(7H-purin-6-ylamino)methylidene]propanedial
• 化学式: C₉H₇N₅O₂
• 分子量: 217.187
• InChiKey: KIYBJEBXENDTGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.05
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100.63
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  三甲酰基甲烷 、 腺嘌呤 以 吡啶 为溶剂， 反应 1.0h， 生成 2-[(7H-purin-6-ylamino)methylidene]propanedial
  参考文献：
  名称：

  Condensation of Triformylmethane with Heteroaromatic Amines, Including Nucleic Acid Bases. A Novel Example of Ring-Chain Tautomerism.

  摘要：

  Treatment of several heteroaromatic amines, including the nucleic acid bases cytosine and adenine, with triformylmethane in pyridine at 70 degrees C afforded 1:1 condensation products (2-11) that were characterized by H-1 and C-13 NMR spectroscopy. All the compounds were assigned as N-substituted aminomethylenemalonaldehydes, strongly preferring the amino/keto form over the imino/enol tautomer. With cytosine and 1-methylcytosine, unequivocal evidence for ring-chain tautomerism was additionally obtained: intramolecular nucleophilic attack of cytosine N3 to one of the carbonyl carbons results in reversible cyclization to a 4-hydroxy-4H-pyrimido[1,6-a]pyrimidin-6(7H)-one derivative (9b, 10b). In dry methanol the corresponding O-methyl ether (12) was obtained.

  DOI：

  10.3891/acta.chem.scand.50-1137

表征谱图