2-bromomethyl-7,8-dimethoxy-5-oxo-1,2-dihydro-5H-oxazolo-[3,2-a]quinoline-4-carboxylic acid isopropylamide | 1265181-61-0

• 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: 2-bromomethyl-7,8-dimethoxy-5-oxo-1,2-dihydro-5H-oxazolo-[3,2-a]quinoline-4-carboxylic acid isopropylamide
• 英文别名: 2-Bromomethyl-7,8-dimethoxy-5-oxo-1,2-dihydro-5h-oxazolo[3,2-a]quinoline-4-carboxylic acid isopropylamide；2-(bromomethyl)-7,8-dimethoxy-5-oxo-N-propan-2-yl-1,2-dihydro-[1,3]oxazolo[3,2-a]quinoline-4-carboxamide
• CAS: 1265181-61-0
• 化学式: C₁₈H₂₁BrN₂O₅
• 分子量: 425.279
• InChiKey: PNABWYJVNQHEJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  di(2-bromomethyl-7,8-dimethoxy-4-isopropylcarbamoyl-1,2-dihydrooxazolo-[3,2-a]quinolinium) ditribromide complex with bromine 在 水 作用下， 以 丙酮 为溶剂， 以72%的产率得到2-bromomethyl-7,8-dimethoxy-5-oxo-1,2-dihydro-5H-oxazolo-[3,2-a]quinoline-4-carboxylic acid isopropylamide
  参考文献：
  名称：

  4-Hydroxy-2-quinolones. 180*. Synthesis, chemical reactions, and analgesic activity of 1-allyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkylamides

  摘要：

  A targeted synthesis was carried out of a series of 1-allyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline- 3-carboxylic acid alkylamides which show interest for biological study as potential analgesics. It was found that, in the presence of one equivalent of bromine, the compounds indicated undergo halocyclization to the corresponding 2-bromomethyl-7,8-dimethoxy-5-oxo-1,2-dihydro-5Hoxa- zolo[3,2-a] quinoline-4-carboxylic acid alkylamides. However, with an excess of bromine the reaction occurs somewhat differently and concludes with the formation of complexes of bromine with 4-alkyl-carbamoyl-2-bromomethyl-5-hydroxy-7,8-dimethoxy-1,2-dihydrooxazolo[3,2-a] quinolinium ditribromides. According to the results of pharmacological screening there are found compounds within the substances discovered with high analgesic activity.

  DOI：

  10.1007/s10593-010-0631-x