5,6-dihydro-8,9-dimethoxy-5-methyl-6-oxobenzophenanthridine-12-carboxylic acid | 143370-39-2

• 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-6-oxobenzophenanthridine-12-carboxylic acid
• 英文别名: 8,9-Dimethoxy-5-methyl-6-oxobenzo[c]phenanthridine-12-carboxylic acid
• CAS: 143370-39-2
• 化学式: C₂₁H₁₇NO₅
• 分子量: 363.37
• InChiKey: FWIWUQOWRBAKDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-dihydro-8,9-dimethoxy-5-methyl-6-oxobenzophenanthridine-12-carboxylic acid 在 铜 作用下， 以 喹啉 为溶剂， 反应 0.25h， 以85%的产率得到8,9-dimethoxy-5-methylbenzophenanthridin-6-one
  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：

  ethyl 5,6-dihydro-8,9-dimethoxy-5-methyl-6-oxobenzophenanthridine-12-carboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以100%的产率得到5,6-dihydro-8,9-dimethoxy-5-methyl-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.