5,8-dimethylisoquinoline-N-oxide | 155826-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5,8-dimethylisoquinoline-N-oxide
• 英文别名: 5,8-Dimethyl-2-oxidoisoquinolin-2-ium
• CAS: 155826-17-8
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: JSZZWJXWYRNLJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  25.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,8-dimethylisoquinoline-N-oxide 在 对甲苯磺酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 以63%的产率得到5,8-dimethylisoquinoline-1-(2H)-one
  参考文献：
  名称：

  Ring D modifications of ellipticine. Part 2. Chlorination of ellipticine via its N-oxide and synthesis and selective acetylation of 5,6,11-trimethyl-5H-benzo[b]carbazole.

  摘要：

  The N-oxide of ellipticine can be used for the introduction of a chlorine atom at carbon-3 of the ellipticine nucleus. According to modelstudies with 5,8-dimethylisoquinoline-N-oxide the reaction is guided both by steric hindrance and by nitrogen-6 of the ellipticine system. Attempted nucleophilic substitution reactions of 3-chloro-ellipticines failed. The high cytostatic activity observed for 9-acetylellipticine stimulated us to prepare the corresponding deaza analogue. This compound was synthesized in 2 steps starting from 1-methylindole. Regioselective acetylation at C-2 was accomplished using acetic anhydride and ZnCl2 as a catalyst. Under a variety of other conditions the 2,9-diacetylproduct was formed and no 9-monoacetylated compound could be isolated. Just as the parent compound, the acetylated deazaellipticines showed only very low cytostatic activity.

  DOI：

  10.1016/s0040-4020(01)85018-3
• 作为产物：
  描述：

  2,5-二甲基苯甲醛 在 硫酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 33.0h， 生成 5,8-dimethylisoquinoline-N-oxide
  参考文献：
  名称：

  Ring D modifications of ellipticine. Part 2. Chlorination of ellipticine via its N-oxide and synthesis and selective acetylation of 5,6,11-trimethyl-5H-benzo[b]carbazole.

  摘要：

  The N-oxide of ellipticine can be used for the introduction of a chlorine atom at carbon-3 of the ellipticine nucleus. According to modelstudies with 5,8-dimethylisoquinoline-N-oxide the reaction is guided both by steric hindrance and by nitrogen-6 of the ellipticine system. Attempted nucleophilic substitution reactions of 3-chloro-ellipticines failed. The high cytostatic activity observed for 9-acetylellipticine stimulated us to prepare the corresponding deaza analogue. This compound was synthesized in 2 steps starting from 1-methylindole. Regioselective acetylation at C-2 was accomplished using acetic anhydride and ZnCl2 as a catalyst. Under a variety of other conditions the 2,9-diacetylproduct was formed and no 9-monoacetylated compound could be isolated. Just as the parent compound, the acetylated deazaellipticines showed only very low cytostatic activity.

  DOI：

  10.1016/s0040-4020(01)85018-3

文献信息

• Ring D modifications of ellipticine. Part 2. Chlorination of ellipticine via its N-oxide and synthesis and selective acetylation of 5,6,11-trimethyl-5H-benzo[b]carbazole.
  作者：Adrian T. Boogaard、Upendra K. Pandit、Gerrit-Jan Koomen

  DOI：10.1016/s0040-4020(01)85018-3

  日期：1994.4

  The N-oxide of ellipticine can be used for the introduction of a chlorine atom at carbon-3 of the ellipticine nucleus. According to modelstudies with 5,8-dimethylisoquinoline-N-oxide the reaction is guided both by steric hindrance and by nitrogen-6 of the ellipticine system. Attempted nucleophilic substitution reactions of 3-chloro-ellipticines failed. The high cytostatic activity observed for 9-acetylellipticine stimulated us to prepare the corresponding deaza analogue. This compound was synthesized in 2 steps starting from 1-methylindole. Regioselective acetylation at C-2 was accomplished using acetic anhydride and ZnCl2 as a catalyst. Under a variety of other conditions the 2,9-diacetylproduct was formed and no 9-monoacetylated compound could be isolated. Just as the parent compound, the acetylated deazaellipticines showed only very low cytostatic activity.