10,11-dimethoxy-N-methyl-7,8-dihydrobenzophenanthridine-9,12-diol | 185384-57-0

• 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: 10,11-dimethoxy-N-methyl-7,8-dihydrobenzophenanthridine-9,12-diol
• 英文别名: 8,9-dimethoxy-5-methyl-6H-benzo[c]phenanthridine-7,10-diol
• CAS: 185384-57-0
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: RQUPKSPTABDADQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  10,11-dimethoxy-N-methyl-7,8-dihydrobenzophenanthridine-9,12-diol 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 7,8,9,10-Tetramethoxy-5-methyl-5,6-dihydro-benzo[c]phenanthridine
  参考文献：
  名称：

  Rearrangements of Cyclobutenones. Synthesis of N-Methyl-7,8-dihydrobenzophenanthridine-9,12-diols and Related Compounds

  摘要：

  A useful synthetic route to benzophenanthridines and annulated derivatives is reported. These arise from the thermolysis (refluxing chlorobenzene) of squaric acid-derived C(3-N-methyl-N-arylpropynyl)-cyclobutenones via a mechanism which involves an electrocyclic ring opening of the cyclobutenone to the corresponding enynylketenes. Subsequent ring closure to a diradical intermediate followed by radical arylation gives the benzophenanthridines.

  DOI：

  10.1021/jo990505b
• 作为产物：
  描述：

  2,3-dimethoxy-4-hydroxy-4-{3-[N-methyl-(1-naphthyl)amino]-1-propynyl}-2-cyclobuten-1-one 以 氯苯 为溶剂， 反应 2.0h， 以68%的产率得到10,11-dimethoxy-N-methyl-7,8-dihydrobenzophenanthridine-9,12-diol
  参考文献：
  名称：

  Ring Expansion of 4-Alkynylcyclobutenones. Synthesis of Piperidinoquinones, Highly Substituted Dihydrophenanthridines, Benzophenanthridines, and the Naturally Occurring Pyrrolophenanthridine, Assoanine

  摘要：

  New synthetic routes to a variety of N-heterocyclic quinones and hydroquinones are described. These include thermolyses of 4-hydroxy-4-[4-N-(benzenesulfonyl)-4-aza-1,6-dialkynyl]cyclobutenones to piperidinoquinones and 4-hydroxy-4-[3-(N-phenylamino)-1-propynyl] cyclobutenones to dihydrophenanthridinediols. Included in the array of products available by this method are benzophenanthridines, indolophenanthridines, isoindoloindoles, and pyrrolophenanthridines. The methodology was employed in a five-step synthesis of the alkaloid assoanine starting with dimethyl squarate and indoline. The key step in all of these transformations is the ring expansion of appropriately substituted 4-hydroxy-4-alkynylcyclobutenones. These are envisaged to undergo electrocyclic ring opening to the corresponding enynylketenes which ring close to diradical intermediates that then lead to products via either radical additions to proximal alkyne moieties or undergo homolytic aromatic substitution to appropriately placed aryl groups. The synthetic scope and mechanism of the ring expansion reactions are discussed.

  DOI：

  10.1021/jo9613803