3-Cyano-quinoline-2-carboxylic acid methyl ester | 142188-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-Cyano-quinoline-2-carboxylic acid methyl ester
• 英文别名: Methyl 3-cyanoquinoline-2-carboxylate
• CAS: 142188-36-1
• 化学式: C₁₂H₈N₂O₂
• 分子量: 212.208
• InChiKey: RNIIXPNFVVJIRO-UHFFFAOYSA-N

物化性质

• 沸点：
  420.8±30.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  63
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 potassium cyanide 作用下， 以 水 为溶剂， 以43%的产率得到4-Cyano-3-methyl-3,4-dihydro-quinazoline-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Reaction of N-vinylpyrazolium and N-vinylindazolium salts with cyanide ion: formation of 1,2-dihydropyrimidines, 3,4-dihydroquinazolines, and quinolines

  摘要：

  The reaction of 1-aryl-2-vinylpyrazolium tetrafluoroborates with potassium cyanide affords 2-hydroxy-1,2-dihydropyrimidines 3, which exist as open-chain tautomers 4, both in the solid state and in solution. The X-ray structure of the p-chlorophenyl derivative 4b has been determined (ClC14N2O3H15, P2(1)/c, a = 11.433 (3) angstrom, b = 16.086 (4) angstrom, c = 7.813 (4) angstrom, beta = 94.22 (5)-degrees, V = 1433.0 (9), Z = 4, R = 0.06 for 1334 observed reflections). Protonation of these vinylogous amidines 4 results in their cyclization and dehydration to pyrimidinium salts 6. In the case of 1-vinyl-2-methylindazolium tetrafluoroborate 8, the reaction with cyanide ion leads to a mixture of 3,4-dihydroquinazoline 12 and 2-(methoxycarbonyl)-3-cyanoquinoline (13). The mechanism proposed for this rearrangement is supported by the isolation of the open-chain intermediate in the case of 1-vinyl-2-phenylindazolium salt.

  DOI：

  10.1021/jo00041a018

表征谱图