3-benzoyl-8,9-diethoxy-1,5,6,10b-tetrahydro-10b-methyl-1-phenyl-1,2,4-triazolo[3,4-a]isoquinoline

• 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: 3-benzoyl-8,9-diethoxy-1,5,6,10b-tetrahydro-10b-methyl-1-phenyl-1,2,4-triazolo[3,4-a]isoquinoline
• 英文别名: (8,9-Diethoxy-10b-methyl-1-phenyl-5,6-dihydro-[1,2,4]triazolo[3,4-a]isoquinolin-3-yl)-phenylmethanone
• 化学式: C₂₈H₂₉N₃O₃
• 分子量: 455.557
• InChiKey: BBUXKTLUYQZZRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-甲基-6,7-二乙氧基-3,4-二氢异喹啉 、 C-benzoyl-N-phenylnitrilimine 以 四氢呋喃 为溶剂， 反应 6.0h， 以81%的产率得到3-benzoyl-8,9-diethoxy-1,5,6,10b-tetrahydro-10b-methyl-1-phenyl-1,2,4-triazolo[3,4-a]isoquinoline
  参考文献：
  名称：

  New Routes to Fused Isoquinolines

  摘要：

  Treatment of 6.7-diethoxy-3,4-dihydroisoquinoline (8) and its 1-methyl derivative 12 with hydrazonoyl halides, 10 in the presence of Et3N in THF under reflux afforded the corresponding 5,6-dihydro-1,2,4-triazolo[3,4-a]isoquinolines 11 and 13. respectively, in high yield (Schemes 2 and 3.). The products are formed via regioselective 1,3-dipolar cycloaddition of the intermediate nitrilimines 9 with the isoquinoline C=N bond. Reaction of 6,7-diethoxy-3,4-dihydroisoquinoline-1-acetonitrile (4a) with ethyl alpha-cyanocinnamates 15 in the presence of piperidine m refluxing MeCN yielded benzo[a]quinolizin-4-ones 16 (Scheme 4), Under the same conditions. 12 and arylidene malononitriles 19 reacted to give benzo[a]quinolizin-4-imines 20 (Scheme5). Instead of 15 and 19, mixtures of an aromatic aldehyde. and ethyl cyanoacetate or malononitrile. respectively can be used in a one-pot reaction.

  DOI：

  10.1002/1522-2675(200201)85:1<320::aid-hlca320>3.0.co;2-x