4,11-dimethoxy-1H-naphtho[2,3-f]indole-2,3,5,10-tetraone | 1181813-22-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4,11-dimethoxy-1H-naphtho[2,3-f]indole-2,3,5,10-tetraone
• 英文别名: 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-dione；4,11-dimethoxy-1H-naphtho[2,3-f]indole-2,3,5,10-tetrone
• CAS: 1181813-22-8
• 化学式: C₁₈H₁₁NO₆
• 分子量: 337.288
• InChiKey: XVHJLAJXDIBVSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  98.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,11-dimethoxy-1H-naphtho[2,3-f]indole-2,3,5,10-tetraone 在 五氯化磷 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.17h， 生成 2-(tert-butylamino)-4,11-dimethoxy-3H-naphtho[2,3-f]indole-3,5,10-trione
  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：

  2,3,3-trichloro-4,11-dimethoxy-3H-naphtho[2,3-f]indole-5,10-dione 在 水 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 以86%的产率得到4,11-dimethoxy-1H-naphtho[2,3-f]indole-2,3,5,10-tetraone
  参考文献：
  名称：

  Heterocyclic analogs of 5,12-naphthacenequinone 7*. Synthesis of naphtho-[2,3-f]isatin-5,10-dione derivatives

  摘要：

  On chlorination of 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione with sulfuryl chloride in chloroform, its mono-, di-, and trichloro derivatives are formed depending on the conditions. Hydrolysis of the di- and trichloro derivatives gives a new polycondensed derivative of isatin, 4,11-dimethoxynaphtho-[2,3-f]isatin-5,10-dione. Its demethylation occurs effectively on extended heating with HBr in acetic acid and leads to 4,11-dihydroxynaphtho[2,3-f]isatin-5,10-dione (4,11-di-hydroxynaphtho[2,3-f]indole-2,3,5,10-tetraone).

  DOI：

  10.1007/s10593-009-0173-2