5,6-dihydro-8,9-dimethoxy-5-methyl-2,3-(methylenedioxy)-6-oxobenzophenanthridine-12-carboxylic acid | 143370-40-5

• 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: 5,6-dihydro-8,9-dimethoxy-5-methyl-2,3-(methylenedioxy)-6-oxobenzophenanthridine-12-carboxylic acid
• 英文别名: 2,3-Dimethoxy-12-methyl-13-oxo-[1,3]benzodioxolo[5,6-c]phenanthridine-6-carboxylic acid
• CAS: 143370-40-5
• 化学式: C₂₂H₁₇NO₇
• 分子量: 407.379
• InChiKey: WWVLIVGSOPHJNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5,6-dihydro-8,9-dimethoxy-5-methyl-2,3-(methylenedioxy)-6-oxobenzophenanthridine-12-carboxylic acid 在 2,2'-联吡啶 、 铜 、 copper(II) acetylacetonate 作用下， 以 喹啉 为溶剂， 反应 0.5h， 以72%的产率得到oxynitidine
  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 在 盐酸 、 氢氧化钾 、 sodium methylate 、 乙酸酐 、 亚硝酸异戊酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.92h， 生成 5,6-dihydro-8,9-dimethoxy-5-methyl-2,3-(methylenedioxy)-6-oxobenzophenanthridine-12-carboxylic acid
  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.