2-[[(1-methyl-2-oxopyrimidin-4-yl)amino]methylidene]propanedial | 185846-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-[[(1-methyl-2-oxopyrimidin-4-yl)amino]methylidene]propanedial
• CAS: 185846-28-0
• 化学式: C₉H₉N₃O₃
• 分子量: 207.189
• InChiKey: FYJZDXGRQNGZBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.53
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  81.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-[[(1-methyl-2-oxopyrimidin-4-yl)amino]methylidene]propanedial 反应 8.0h， 生成 Uhxbymiraphpdx-uhfffaoysa-
  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
• 作为产物：
  描述：

  1-甲基胞嘧啶 、 三甲酰基甲烷 以 吡啶 为溶剂， 反应 1.0h， 生成 2-[[(1-methyl-2-oxopyrimidin-4-yl)amino]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

文献信息

• Condensation of Triformylmethane with Heteroaromatic Amines, Including Nucleic Acid Bases. A Novel Example of Ring-Chain Tautomerism.
  作者：Kari Neuvonen、Carmela Zewi、Harri Lönnberg、Yincai Su、Markku Leskelä、Mika Polamo、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-1137

  日期：——

  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.