8,9-Dimethoxy-10b-methyl-5-phenyl-6,10b-dihydro-5H-oxazolo[2,3-a]isoquinoline-2,3-dione | 135365-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 8,9-Dimethoxy-10b-methyl-5-phenyl-6,10b-dihydro-5H-oxazolo[2,3-a]isoquinoline-2,3-dione
• CAS: 135365-14-9
• 化学式: C₂₀H₁₉NO₅
• 分子量: 353.375
• InChiKey: UHPQDBWTNGVWKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  8,9-Dimethoxy-10b-methyl-5-phenyl-6,10b-dihydro-5H-oxazolo[2,3-a]isoquinoline-2,3-dione 在 硫酸 作用下， 以 甲醇 为溶剂， 生成 6,7-dimethoxy-1-methyl-3-phenyl-3,4-dihydroisoquinoline
  参考文献：
  名称：

  A modified Bischler-Napieralski procedure for the synthesis of 3-aryl-3,4-dihydroisoquinolines

  摘要：

  A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.

  DOI：

  10.1021/jo00021a014
• 作为产物：
  描述：

  2-(3,4-二甲氧基苯基)-N-甲氧基-N-甲基乙酰胺 在 盐酸 、 sodium hydroxide 、 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 8,9-Dimethoxy-10b-methyl-5-phenyl-6,10b-dihydro-5H-oxazolo[2,3-a]isoquinoline-2,3-dione
  参考文献：
  名称：

  A modified Bischler-Napieralski procedure for the synthesis of 3-aryl-3,4-dihydroisoquinolines

  摘要：

  A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.

  DOI：

  10.1021/jo00021a014