ethyl 4-(furan-2-yl)-2-methylquinoline-3-carboxylate | 1072913-37-1

• 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: ethyl 4-(furan-2-yl)-2-methylquinoline-3-carboxylate
• CAS: 1072913-37-1
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: FRQKVMOZQWZBPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-丁酮酸乙酯 、 (2-aminophenyl)(furan-2-yl)methanol 在 iron(III) chloride 、 氧气 、 zinc(II) chloride 作用下， 以 氯苯 为溶剂， 反应 12.0h， 以92%的产率得到ethyl 4-(furan-2-yl)-2-methylquinoline-3-carboxylate
  参考文献：
  名称：

  Cascade Synthesis of 3-Quinolinecarboxylic Ester via Benzylation/ Propargylation−Cyclization

  摘要：

  Reactions of 2-amino-aryl alcohols with beta-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation-cyclization, 2-nitrophenyl proparoyl alcohols with beta-ketoesters catalyzed by FeCl3 and SnCl, also produce the 4-alkyne-3-quitiolinecarboxylic esters. The mechanistic details of this benzylation/proparoylation and cyclization cascade process are also discussed.

  DOI：

  10.1021/jo8017654

文献信息

• Cascade Synthesis of 3-Quinolinecarboxylic Ester via Benzylation/ Propargylation−Cyclization
  作者：Jinmin Fan、Changfeng Wan、Gaojun Sun、Zhiyong Wang

  DOI：10.1021/jo8017654

  日期：2008.11.7

  Reactions of 2-amino-aryl alcohols with beta-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation-cyclization, 2-nitrophenyl proparoyl alcohols with beta-ketoesters catalyzed by FeCl3 and SnCl, also produce the 4-alkyne-3-quitiolinecarboxylic esters. The mechanistic details of this benzylation/proparoylation and cyclization cascade process are also discussed.