1,8-dimethyl-3,5-dinitro-2-quinolone | 1433884-38-8

• 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: 1,8-dimethyl-3,5-dinitro-2-quinolone
• 英文别名: 1,8-Dimethyl-3,5-dinitroquinolin-2-one；1,8-dimethyl-3,5-dinitroquinolin-2-one
• CAS: 1433884-38-8
• 化学式: C₁₁H₉N₃O₅
• 分子量: 263.21
• InChiKey: IEFXRIZDPMSFBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 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：
  112
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  potassium cyanide 、 1,8-dimethyl-3,5-dinitro-2-quinolone 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 以47%的产率得到1,8-dimethyl-5-nitro-2-oxo-1,2-dihydroquinoline-4-carbonitrile
  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
• 作为产物：
  描述：

  8-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 1,8-dimethyl-3,5-dinitro-2-quinolone
  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

• Direct amino-halogenation and aziridination of the 2-quinolone framework by sequential treatment of 3-nitro-2-quinolone with amine and N-halosuccinimide
  作者：Feiyue Hao、Haruyasu Asahara、Nagatoshi Nishiwaki

  DOI：10.1016/j.tet.2017.01.028

  日期：2017.3

  sequential treatment of 3-nitro-2-quinolones with amines and N-halosuccinimides under mild conditions facilitated the direct amino-halogenation and aziridination at the 4- and 3-positions of the 2-quinolone framework. The selectivity of the functionalization was influenced by the electronic properties of the substituents on the benzene moiety of the nitroquinolone. The electron-withdrawing nitro group

  胺和氮对3-硝基-2-喹诺酮类药物的序贯处理-卤代琥珀酰亚胺在温和条件下促进了2-喹诺酮骨架的4-位和3-位的直接氨基卤化和叠氮化。官能化的选择性受硝基喹诺酮苯部分上取代基的电子性质的影响。吸电子的硝基促进了氨基的卤代，并且用卤素或氢取代硝基显着提高了叠氮化的选择性。此外，在4-位引入琥珀酰亚胺基团而不是烷基氨基基团，提供了4-氨基-3-氯-2-喹诺酮衍生物的掩蔽形式。此外，使制得的双官能化喹诺酮经受Suzuki-Miyaura偶联反应，开环和肼解，得到不同官能化的喹诺酮。
• A direct and vicinal functionalization of the 1-methyl-2-quinolone framework: 4-alkoxylation and 3-chlorination
  作者：Feiyue Hao、Haruyasu Asahara、Nagatoshi Nishiwaki

  DOI：10.1039/c6ob00868b

  日期：——

  Bis(functionalization), 4-alkoxylation and 3-chlorination, of the 1-methyl-2-quinolone framework was achieved by a sequential treatment of 3-nitrated 2-quinolones with sodium alkoxide and NCS.

  1-甲基-2-喹啉骨架的双官能团化，4-烷氧化和3-氯化，通过将3-硝化的2-喹啉与钠烷氧化物和NCS顺序处理而实现。
• 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.