4-formamido-3-(2-methoxy-4,5-methylenedioxyphenyl)-6,7-methylenedioxy-1-naphthol | 168098-79-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-formamido-3-(2-methoxy-4,5-methylenedioxyphenyl)-6,7-methylenedioxy-1-naphthol
• CAS: 168098-79-1
• 化学式: C₂₀H₁₅NO₇
• 分子量: 381.342
• InChiKey: TYEGWHQKDAARHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  95.48
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 4-formamido-3-(2-methoxy-4,5-methylenedioxyphenyl)-6,7-methylenedioxy-1-naphthol 在 苄基三丁基氯化铵 sodium hydroxide 作用下， 以 氯仿 为溶剂， 反应 72.0h， 以70%的产率得到4-methoxy-2-(2-methoxy-4,5-methylenedioxyphenyl)-1-(N-methylformamido)-6,7-methylenedioxynaphthalene
  参考文献：
  名称：

  Synthesis of macarpine and its cytotoxicity: Toward a synthetic route for 12-alkoxybenzo[c]phenanthridine alkaloids through aromatic nitrosation under basic condition

  摘要：

  Macarpine (1), a 2, 3, 7, 8, 10, 12-hexaoxygenated benzo[c]phenanthridine alkaloid (O-6 base), was effectively synthesized from sesamol methyl ether (7) through the newly developed aromatic nitrosation under basic condition. The tests for the cytotoxicity of 1 and its analogous 2, 3, 7, 8, 10-pentaoxygenated (O-5) bases 23, 24 against HeLa S3 tumor cell showed that 1 exhibited the highest activity among them.

  DOI：

  10.1016/0040-4020(95)00460-p
• 作为产物：
  描述：

  甲酸 、 (Z)-2-(2-methoxy-4,5-methylenedioxyphenyl)-1-methoxyimino-6,7-methylenedioxynaphthalen-4(2H)-one 在 palladium on activated charcoal 氢气 作用下， 生成 4-formamido-3-(2-methoxy-4,5-methylenedioxyphenyl)-6,7-methylenedioxy-1-naphthol
  参考文献：
  名称：

  Synthesis of macarpine and its cytotoxicity: Toward a synthetic route for 12-alkoxybenzo[c]phenanthridine alkaloids through aromatic nitrosation under basic condition

  摘要：

  Macarpine (1), a 2, 3, 7, 8, 10, 12-hexaoxygenated benzo[c]phenanthridine alkaloid (O-6 base), was effectively synthesized from sesamol methyl ether (7) through the newly developed aromatic nitrosation under basic condition. The tests for the cytotoxicity of 1 and its analogous 2, 3, 7, 8, 10-pentaoxygenated (O-5) bases 23, 24 against HeLa S3 tumor cell showed that 1 exhibited the highest activity among them.

  DOI：

  10.1016/0040-4020(95)00460-p