[(7-氯-6-氟-3-甲酰基喹啉-2-基)硫代]乙酸乙酯 | 1013105-79-7

• 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
• 中文名称: [(7-氯-6-氟-3-甲酰基喹啉-2-基)硫代]乙酸乙酯
• 英文名称: ethyl [(7-chloro-6-fluoro-3-formylquinolin-2-yl)thio]acetate
• CAS: 1013105-79-7
• 化学式: C₁₄H₁₁ClFNO₃S
• 分子量: 327.764
• InChiKey: WAOABDBFOMTHMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  56.26
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(7-氯-6-氟-3-甲酰基喹啉-2-基)硫代]乙酸乙酯 以 N,N-二甲基甲酰胺 为溶剂， 以69%的产率得到ethyl 7-chloro-6-fluorothieno[2,3-b]quinoline-2-carboxylate
  参考文献：
  名称：

  Chemistry of Substituted Quinolines: Thieno[2,3- b ] and Thiopyrano[2,3- b ]quinolines

  摘要：

  The reaction of 3-formyl-2-chloroquinolines with thioglycolic acid afforded a mixture of uncyclized [(3-formylquinolin-2-yl)thio]acetic acid in a 60-70% yield and cyclized thieno[2,3-b]quinoline-2-carboxylic acids in a 30-40% yield, respectively. The uncyclized compounds on refluxing with POCl3 in various alcoholic media gave [(3-formylquinolin-2-yl)thio]acetates. Further cyclization was achieved by refluxing them with dimethylformamide (DMF) to produce thieno[2,3-b]quinoline derivatives. On the other hand, the reaction of 3-formyl-2-mercaptoquinolines with chloroacetyl chloride in DMF gave 3-chloro-2H-thiopyrano[2,3-b]quinolin-2-ones. The structures of all the newly synthesized compounds were characterized on the basis of elemental analysis, IR, H-1 NMR, and mass spectral data.

  DOI：

  10.1080/10426500601088846
• 作为产物：
  描述：

  7-chloro-6-fluoro-2-mercaptoquinoline-3-carbaldehyde 在 potassium carbonate 、 三氯氧磷 作用下， 以 丙酮 为溶剂， 生成 [(7-氯-6-氟-3-甲酰基喹啉-2-基)硫代]乙酸乙酯
  参考文献：
  名称：

  Chemistry of Substituted Quinolines: Thieno[2,3- b ] and Thiopyrano[2,3- b ]quinolines

  摘要：

  The reaction of 3-formyl-2-chloroquinolines with thioglycolic acid afforded a mixture of uncyclized [(3-formylquinolin-2-yl)thio]acetic acid in a 60-70% yield and cyclized thieno[2,3-b]quinoline-2-carboxylic acids in a 30-40% yield, respectively. The uncyclized compounds on refluxing with POCl3 in various alcoholic media gave [(3-formylquinolin-2-yl)thio]acetates. Further cyclization was achieved by refluxing them with dimethylformamide (DMF) to produce thieno[2,3-b]quinoline derivatives. On the other hand, the reaction of 3-formyl-2-mercaptoquinolines with chloroacetyl chloride in DMF gave 3-chloro-2H-thiopyrano[2,3-b]quinolin-2-ones. The structures of all the newly synthesized compounds were characterized on the basis of elemental analysis, IR, H-1 NMR, and mass spectral data.

  DOI：

  10.1080/10426500601088846