2,3-dimethoxy-4-hydroxy-4-[3-[N-methyl-N-[1-(6,7-methylenedioxy)naphthyl]amino]-1-propynyl]-2-cyclobuten-1-one | 238431-89-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-dimethoxy-4-hydroxy-4-[3-[N-methyl-N-[1-(6,7-methylenedioxy)naphthyl]amino]-1-propynyl]-2-cyclobuten-1-one
• 英文别名: 4-[3-[Benzo[f][1,3]benzodioxol-5-yl(methyl)amino]prop-1-ynyl]-4-hydroxy-2,3-dimethoxycyclobut-2-en-1-one
• CAS: 238431-89-5
• 化学式: C₂₁H₁₉NO₆
• 分子量: 381.385
• InChiKey: WNBDRPBWUUMRAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-dimethoxy-4-hydroxy-4-[3-[N-methyl-N-[1-(6,7-methylenedioxy)naphthyl]amino]-1-propynyl]-2-cyclobuten-1-one 以 氯苯 为溶剂， 生成 2,3-Dimethoxy-12-methyl-12,13-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine-1,4-diol
  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：

  naphtho[2,3-d][1,3]dioxol-5-amine 在 T406石油添加剂 、 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.42h， 生成 2,3-dimethoxy-4-hydroxy-4-[3-[N-methyl-N-[1-(6,7-methylenedioxy)naphthyl]amino]-1-propynyl]-2-cyclobuten-1-one
  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

文献信息

• Rearrangements of Cyclobutenones. Synthesis of <i>N</i>-Methyl-7,8-dihydrobenzophenanthridine-9,12-diols and Related Compounds
  作者：Antonio R. Hergueta、Harold W. Moore

  DOI：10.1021/jo990505b

  日期：1999.8.1

  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.