1,6-dimethyl-3,5,7-trinitroquinolin-2(1H)-one | 1433884-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,6-dimethyl-3,5,7-trinitroquinolin-2(1H)-one
• 英文别名: 1,6-Dimethyl-3,5,7-trinitroquinolin-2-one；1,6-dimethyl-3,5,7-trinitroquinolin-2-one
• CAS: 1433884-10-6
• 化学式: C₁₁H₈N₄O₇
• 分子量: 308.207
• InChiKey: UUTJUURYNSFZIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 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：
  158
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-甲基喹啉 在 硫酸 、 硝酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 生成 1,6-dimethyl-3,5,7-trinitroquinolin-2(1H)-one 、 1,6-dimethyl-5,7-dinitroquinolin-2(1H)-one 、 1,6-dimethyl-3,5-dinitroquinolin-2(1H)-one
  参考文献：
  名称：

  Reactive 2-quinolones dearomatized by steric repulsion between 1-methyl and 8-substituted groups

  摘要：

  Usual 1-methyl-2-quinolone (MeQone) derivatives are not reactive because of aromatic property in the heterocyclic ring. On the other hand, 8-substituted MeQones have been proved to be highly reactive, which is caused by steric repulsion between the 1-methyl and the 8-substituted groups. When 1-methyl-3,6,8-trinitro-2-quinolone was treated with potassium (or trimethylsilyl) cyanide, cyanation proceeded at the 4-position regioselectively as a result of cine-substitution. This reaction is initiated with addition of cyanide species, and the cyanoquinolone is formed by the protonation of the resultant anionic intermediate followed by elimination of nitrous acid. The high reactivity was maintained even when one of the nitro groups on the benzene moiety was replaced by a methyl group, which afforded corresponding cine-substituted products upon treatment with potassium cyanide. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.008

文献信息

• Reactive 2-quinolones dearomatized by steric repulsion between 1-methyl and 8-substituted groups
  作者：Xin Chen、Kazuya Kobiro、Haruyasu Asahara、Kiyomi Kakiuchi、Ryuichi Sugimoto、Kazuhiko Saigo、Nagatoshi Nishiwaki

  DOI：10.1016/j.tet.2013.04.008

  日期：2013.6

  Usual 1-methyl-2-quinolone (MeQone) derivatives are not reactive because of aromatic property in the heterocyclic ring. On the other hand, 8-substituted MeQones have been proved to be highly reactive, which is caused by steric repulsion between the 1-methyl and the 8-substituted groups. When 1-methyl-3,6,8-trinitro-2-quinolone was treated with potassium (or trimethylsilyl) cyanide, cyanation proceeded at the 4-position regioselectively as a result of cine-substitution. This reaction is initiated with addition of cyanide species, and the cyanoquinolone is formed by the protonation of the resultant anionic intermediate followed by elimination of nitrous acid. The high reactivity was maintained even when one of the nitro groups on the benzene moiety was replaced by a methyl group, which afforded corresponding cine-substituted products upon treatment with potassium cyanide. (C) 2013 Elsevier Ltd. All rights reserved.