2-[(3,4-Dimethoxyphenyl)methyl-[(3-methoxyphenyl)methyl]amino]-1-phenylethanone | 206125-90-8

• 英文名称: 2-[(3,4-Dimethoxyphenyl)methyl-[(3-methoxyphenyl)methyl]amino]-1-phenylethanone
• CAS: 206125-90-8
• 化学式: C₂₅H₂₇NO₄
• 分子量: 405.494
• InChiKey: MHQOCAHAMKRUQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(3,4-Dimethoxyphenyl)methyl-[(3-methoxyphenyl)methyl]amino]-1-phenylethanone 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以62%的产率得到4,5,13-Trimethoxy-1-phenyl-9-azatetracyclo[7.7.1.02,7.011,16]heptadeca-2,4,6,11(16),12,14-hexaene
  参考文献：
  名称：

  Synthesis of 7,12-Dihydro-12-phenyl-5H-6,12-methanodibenz[c,f]azocines via N,N-Dibenzylphenacylamines

  摘要：

  N,N-Dibenzylphenacylamines (1) were prepared in high yields by a one-pot reaction and cyclized at room temperature to give 7,12-dihydro-l2-phenyl-5H-6,1 2-methanodibenz[c,f]azocines in high yields. 95% H2SO4 or 70% HClO4 was used as cycIization catalysts. The double-cyclization proceeds smoothly in the cases where electron-donating groups are present in both benzene ring. N-2,3-dimethoxybenzyl-N-benzylphenacylamine (1f) gave the corresponding N-benzyl-1,2-dihydro-4-phenylisoquinoline on treatment with 95% H2SO4 while N-3,4-Dimethoxybenzyl-N-benzylphenacylamine (1a) at the same reaction conditions and reaction time cyclized to the corresponding dibenzazocine. However 1a gave the corresponding dihydroisoquinoline which disproportionates to give N-benzyl-1,2,3,4-tetrahydro-4-phenylisoquinoline and N-benzyl-4-phenylisoquinolinium when treated with 70% perchloric acid al room temperature.

  DOI：

  10.3987/com-97-7986
• 作为产物：
  描述：

  在 钾硼氢 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 2-[(3,4-Dimethoxyphenyl)methyl-[(3-methoxyphenyl)methyl]amino]-1-phenylethanone
  参考文献：
  名称：

  Synthesis of 7,12-Dihydro-12-phenyl-5H-6,12-methanodibenz[c,f]azocines via N,N-Dibenzylphenacylamines

  摘要：

  N,N-Dibenzylphenacylamines (1) were prepared in high yields by a one-pot reaction and cyclized at room temperature to give 7,12-dihydro-l2-phenyl-5H-6,1 2-methanodibenz[c,f]azocines in high yields. 95% H2SO4 or 70% HClO4 was used as cycIization catalysts. The double-cyclization proceeds smoothly in the cases where electron-donating groups are present in both benzene ring. N-2,3-dimethoxybenzyl-N-benzylphenacylamine (1f) gave the corresponding N-benzyl-1,2-dihydro-4-phenylisoquinoline on treatment with 95% H2SO4 while N-3,4-Dimethoxybenzyl-N-benzylphenacylamine (1a) at the same reaction conditions and reaction time cyclized to the corresponding dibenzazocine. However 1a gave the corresponding dihydroisoquinoline which disproportionates to give N-benzyl-1,2,3,4-tetrahydro-4-phenylisoquinoline and N-benzyl-4-phenylisoquinolinium when treated with 70% perchloric acid al room temperature.

  DOI：

  10.3987/com-97-7986