2-(benzoylamino)-5,6-dihydro-8,9-dimethoxy-5-methyl-3,6-dioxo-3H-pyrano<2,3-c>isoquinoline | 143370-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(benzoylamino)-5,6-dihydro-8,9-dimethoxy-5-methyl-3,6-dioxo-3H-pyrano<2,3-c>isoquinoline
• 英文别名: N-(8,9-dimethoxy-5-methyl-3,6-dioxopyrano[2,3-c]isoquinolin-2-yl)benzamide
• CAS: 143370-27-8
• 化学式: C₂₂H₁₈N₂O₆
• 分子量: 406.395
• InChiKey: JPWWUEVWGFFOHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  邻氨基苯甲酸 、 2-(benzoylamino)-5,6-dihydro-8,9-dimethoxy-5-methyl-3,6-dioxo-3H-pyrano<2,3-c>isoquinoline 在 亚硝酸异戊酯 作用下， 生成 N-(8,9-Dimethoxy-5-methyl-6-oxo-5,6-dihydro-benzo[c]phenanthridin-12-yl)-benzamide 、 12-(benzoylamino)-4b,5,6,12-tetrahydro-8,9-dimethoxy-5-methyl-6-oxo-4b,12-o-benzenobenzophenanthridine
  参考文献：
  名称：

  A new approach to the synthesis of antitumor benzophenanthridine alkaloids. Formal synthesis of nitidine

  摘要：

  The synthesis of benzophenanthridine alkaloids by an efficient new convergent strategy based on the Diels-Alder reaction between an alpha-pyrone and an aryne is described. With minor modifications, norbenzophenanthridines and phenanthridines and their 12-amino derivatives were obtained in good overall yields.

  DOI：

  10.1021/jo00048a025
• 作为产物：
  描述：

  6,7-dimethoxy-2-methylisoquinoline-1,3(2H,4H)-dione 、 methyl 2-benzoylamino-3-dimethylaminopropenoate 在 溶剂黄146 作用下， 反应 3.0h， 以79%的产率得到2-(benzoylamino)-5,6-dihydro-8,9-dimethoxy-5-methyl-3,6-dioxo-3H-pyrano<2,3-c>isoquinoline
  参考文献：
  名称：

  A new approach to the synthesis of antitumor benzophenanthridine alkaloids. Formal synthesis of nitidine

  摘要：

  The synthesis of benzophenanthridine alkaloids by an efficient new convergent strategy based on the Diels-Alder reaction between an alpha-pyrone and an aryne is described. With minor modifications, norbenzophenanthridines and phenanthridines and their 12-amino derivatives were obtained in good overall yields.

  DOI：

  10.1021/jo00048a025

文献信息

• A new approach to the synthesis of antitumor benzophenanthridine alkaloids. Formal synthesis of nitidine
  作者：Dolores Perez、Enrique Guitian、Luis Castedo

  DOI：10.1021/jo00048a025

  日期：1992.10

  The synthesis of benzophenanthridine alkaloids by an efficient new convergent strategy based on the Diels-Alder reaction between an alpha-pyrone and an aryne is described. With minor modifications, norbenzophenanthridines and phenanthridines and their 12-amino derivatives were obtained in good overall yields.