4-methyl-6,7-(methylenedioxy)-9-[(3,4,5-trimethoxyphenyl)imino]-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one | 1020667-78-0

• 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: 4-methyl-6,7-(methylenedioxy)-9-[(3,4,5-trimethoxyphenyl)imino]-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one
• CAS: 1020667-78-0
• 化学式: C₂₂H₂₀N₂O₇
• 分子量: 424.41
• InChiKey: REKHZGNMGRULHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.74
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-methyl-6,7-(methylenedioxy)-9-[(3,4,5-trimethoxyphenyl)imino]-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、1.0 MPa 条件下， 反应 4.0h， 以80%的产率得到4-methyl-6,7-(methylenedioxy)-9-[(3,4,5-trimethoxyphenyl)amino]-3a,4-dihydrofuro[3,4-b]quinolin-1(3H)-one
  参考文献：
  名称：

  Design and Effective Synthesis of the First 4-Aza-2,3-didehydropodophyllotoxin Rigid Aminologue: A N-Methyl-4-[(3,4,5-trimethoxyphenyl)amino)]-1,2-dihydroquinoline-lactone

  摘要：

  [GRPAHICS]The first N1-alkyl-4-amino- 1,2-dihydroquinoline-lactone has been prepared by a five-step sequence in a 51 % overall yield via the corresponding furo[3,4-b]quinolin- 1 (3H)-one. A new practical synthesis of this intermediate was carried out using versatile, commercially available starting materials and constitutes the shortest and highest yielding route. These synthetic pathways could be widened with a view toward the preparation of different substituted derivatives, which could be considered as rigid aminologues of 4-aza-2,3-dide-hydropodophyllotoxins.

  DOI：

  10.1021/jo800166b
• 作为产物：
  描述：

  4-methyl-6,7-(methylenedioxy)-1-oxo-9-[(3,4,5-trimethoxyphenyl)amino]-1,3-dihydrofuro[3,4-b]quinolin-4-ium trifluoromethanesulfonate 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以98%的产率得到4-methyl-6,7-(methylenedioxy)-9-[(3,4,5-trimethoxyphenyl)imino]-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one
  参考文献：
  名称：

  Design and Effective Synthesis of the First 4-Aza-2,3-didehydropodophyllotoxin Rigid Aminologue: A N-Methyl-4-[(3,4,5-trimethoxyphenyl)amino)]-1,2-dihydroquinoline-lactone

  摘要：

  [GRPAHICS]The first N1-alkyl-4-amino- 1,2-dihydroquinoline-lactone has been prepared by a five-step sequence in a 51 % overall yield via the corresponding furo[3,4-b]quinolin- 1 (3H)-one. A new practical synthesis of this intermediate was carried out using versatile, commercially available starting materials and constitutes the shortest and highest yielding route. These synthetic pathways could be widened with a view toward the preparation of different substituted derivatives, which could be considered as rigid aminologues of 4-aza-2,3-dide-hydropodophyllotoxins.

  DOI：

  10.1021/jo800166b