4,11-dimethoxy-1-methyl-1H-naphtho[2,3-f]indole-2,3,5,10-tetraone | 1325667-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4,11-dimethoxy-1-methyl-1H-naphtho[2,3-f]indole-2,3,5,10-tetraone
• 英文别名: 4,11-Dimethoxy-1-methyl-1h-naphtho[2,3-f]indole-2,3,5,10-tetraone；4,11-dimethoxy-1-methylnaphtho[2,3-f]indole-2,3,5,10-tetrone
• CAS: 1325667-20-6
• 化学式: C₁₉H₁₃NO₆
• 分子量: 351.315
• InChiKey: JNCNFTNEOWTVEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,11-dimethoxy-1-methyl-1H-naphtho[2,3-f]indole-2,3,5,10-tetraone 、 氨基硫脲 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以53%的产率得到4,11-dimethoxy-1-methyl-1H-naphtho[2,3-f]indole-2,3,5,10-tetraone (3Z)-3-thiosemicarbazone
  参考文献：
  名称：

  Heterocyclic analogs of 5,12-naphthacenequinone 9*. Study of the synthesis and reactivity of 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones

  摘要：

  A preparative method has been developed for N-alkyl 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones. Condensation reactions with several N- and C-nucleophiles have been carried out to give the corresponding derivatives at position 3. An efficient method has been discovered for the demethylation of the N-alkyl-4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones to give a high yield of N-substituted 4,11-dihydroxynaphtho[2,3-f]isatin-5,10-diones. Successive halogenation using phosphorus pentachloride and acylation of tert-butylamine by the intermediate 2-chloro derivative converted 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-dione to the 2-amino-3H-naphtho[2,3-f]indole-3,5,10-trione derivative.

  DOI：

  10.1007/s10593-011-0740-1
• 作为产物：
  描述：

  4,11-dimethoxy-1-methylnaphtho[2,3-f]indole-5,10-dione 在 磺酰氯 、 水 、 sodium acetate 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 25.0h， 以65%的产率得到4,11-dimethoxy-1-methyl-1H-naphtho[2,3-f]indole-2,3,5,10-tetraone
  参考文献：
  名称：

  Heterocyclic analogs of 5,12-naphthacenequinone 9*. Study of the synthesis and reactivity of 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones

  摘要：

  A preparative method has been developed for N-alkyl 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones. Condensation reactions with several N- and C-nucleophiles have been carried out to give the corresponding derivatives at position 3. An efficient method has been discovered for the demethylation of the N-alkyl-4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones to give a high yield of N-substituted 4,11-dihydroxynaphtho[2,3-f]isatin-5,10-diones. Successive halogenation using phosphorus pentachloride and acylation of tert-butylamine by the intermediate 2-chloro derivative converted 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-dione to the 2-amino-3H-naphtho[2,3-f]indole-3,5,10-trione derivative.

  DOI：

  10.1007/s10593-011-0740-1

文献信息

• Heterocyclic analogs of 5,12-naphthacenequinone 9*. Study of the synthesis and reactivity of 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones
  作者：A. N. Nikitina、A. E. Shchekotikhin、Y. N. Luzikov、A. M. Korolev、V. N. Buyanov、M. N. Preobrazhenskaya

  DOI：10.1007/s10593-011-0740-1

  日期：2011.5

  A preparative method has been developed for N-alkyl 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones. Condensation reactions with several N- and C-nucleophiles have been carried out to give the corresponding derivatives at position 3. An efficient method has been discovered for the demethylation of the N-alkyl-4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones to give a high yield of N-substituted 4,11-dihydroxynaphtho[2,3-f]isatin-5,10-diones. Successive halogenation using phosphorus pentachloride and acylation of tert-butylamine by the intermediate 2-chloro derivative converted 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-dione to the 2-amino-3H-naphtho[2,3-f]indole-3,5,10-trione derivative.