N-methyl-N-prop-2-ynylbenzo[f][1,3]benzodioxol-5-amine | 238431-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-methyl-N-prop-2-ynylbenzo[f][1,3]benzodioxol-5-amine
• CAS: 238431-90-8
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: KSTNJEIDJHRKQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基-3-环丁烯-1,2-二酮 、 N-methyl-N-prop-2-ynylbenzo[f][1,3]benzodioxol-5-amine 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.42h， 以79%的产率得到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
• 作为产物：
  描述：

  N-Naphtho[2,3-d][1,3]dioxol-5-yl-formamide 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 生成 N-methyl-N-prop-2-ynylbenzo[f][1,3]benzodioxol-5-amine
  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