4-(β-D-ribofuranosyl)quinoline-2-carboxamide | 153751-22-5

• 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: 4-(β-D-ribofuranosyl)quinoline-2-carboxamide
• CAS: 153751-22-5
• 化学式: C₁₅H₁₆N₂O₅
• 分子量: 304.302
• InChiKey: LYYQEJPZQKQVEZ-SYQHCUMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.51
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  125.9
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  丙酮 、 4-(β-D-ribofuranosyl)quinoline-2-carboxamide 在 对甲苯磺酸 作用下， 反应 5.0h， 以43%的产率得到4-(2,3-O-isopropylidene-β-D-ribofuranosyl)quinoline-2-carboxamide
  参考文献：
  名称：

  C-Nucleosides. 23. Synthesis of Enaminone Glycoside and 4-(b-D-Ribofuranosyl)quinoline-2-carboxamide from Furanone Glycoside

  摘要：

  Furanone glycoside (1) was treated with aniline to yield 3-anilino-5-hydroxy-5-(2,3,5-tri-($) under bar O-benzoyl-beta-D-ribofuranosyl)furan-2(5 ($) under bar H)-one (2). Reaction of 2 with trifluoroacetic acid afforded enaminone glycoside (3), whereas treatment of 2 with hydrochloric acid in methanol brought about the ring formation to furnish methyl 4-(2,3,5-tri-($) under bar O-benzoyl-beta-D-ribofuranosyl)quinoline-2-carboxylate (6) together with methyl 2-anilino-4-(3,5-di-($) under bar O-benzoyl-1,4-anhydro-2-deoxy-D-erythropent-1-enofuranosyl)-4-oxobutanoate (4) and methyl 2-anilino-4-(5-benzoyloxymethylfuran-2-yl)-4-oxobutanoate (5) in yields of 12%, 12%, and 7%, respectively. The quinoline ester (6) reacted with aq. ammonia in methanol to produce quinolinecarboxamide ($) under bar C-nucleoside (7).

  DOI：

  10.3987/com-93-6524
• 作为产物：
  描述：

  methyl 4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)quinoline-2-carboxylate 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 192.0h， 以53%的产率得到4-(β-D-ribofuranosyl)quinoline-2-carboxamide
  参考文献：
  名称：

  C-Nucleosides. 23. Synthesis of Enaminone Glycoside and 4-(b-D-Ribofuranosyl)quinoline-2-carboxamide from Furanone Glycoside

  摘要：

  Furanone glycoside (1) was treated with aniline to yield 3-anilino-5-hydroxy-5-(2,3,5-tri-($) under bar O-benzoyl-beta-D-ribofuranosyl)furan-2(5 ($) under bar H)-one (2). Reaction of 2 with trifluoroacetic acid afforded enaminone glycoside (3), whereas treatment of 2 with hydrochloric acid in methanol brought about the ring formation to furnish methyl 4-(2,3,5-tri-($) under bar O-benzoyl-beta-D-ribofuranosyl)quinoline-2-carboxylate (6) together with methyl 2-anilino-4-(3,5-di-($) under bar O-benzoyl-1,4-anhydro-2-deoxy-D-erythropent-1-enofuranosyl)-4-oxobutanoate (4) and methyl 2-anilino-4-(5-benzoyloxymethylfuran-2-yl)-4-oxobutanoate (5) in yields of 12%, 12%, and 7%, respectively. The quinoline ester (6) reacted with aq. ammonia in methanol to produce quinolinecarboxamide ($) under bar C-nucleoside (7).

  DOI：

  10.3987/com-93-6524