3,4-dihydro-4-methyl-3-oxo-7-trifluoromethylquinoxaline-2-carbonitrile-1-oxide | 1345694-34-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3,4-dihydro-4-methyl-3-oxo-7-trifluoromethylquinoxaline-2-carbonitrile-1-oxide
• CAS: 1345694-34-9
• 化学式: C₁₁H₆F₃N₃O₂
• 分子量: 269.183
• InChiKey: OGSYOHZSHAVEKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.73
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  N-methyl-N-<4-(trifluoromethyl)phenyl>cyanoacetamide 在 2,2,6,6-四甲基哌啶氧化物 、 硫酸 、 sodium nitrite 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以79%的产率得到3,4-dihydro-4-methyl-3-oxo-7-trifluoromethylquinoxaline-2-carbonitrile-1-oxide
  参考文献：
  名称：

  A diversity-oriented synthesis of caroverine derivatives via TEMPO-promoted aerobic oxidative CN bond formation

  摘要：

  A concise method has been developed for the synthesis of caroverine and its derivatives. The quinoxalinone scaffold of these compounds was constructed via the tandem nitrosation/aerobic oxidative C N bond formation reaction of N-(2-chloroethyl)-2-cyano-N-phenylacetamide, followed by sequential Grignard, Finkelstein and nucleophilic substitutions reactions to give several different derivatives. Herein, we describe the development of this strategy in terms of the optimization of each step as well as the effect of different additives on the individual reactions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.061

文献信息

• Highly Efficient Synthesis of Quinoxalinone-<i>N</i>-oxide via Tandem Nitrosation/Aerobic Oxidative C–N Bond Formation
  作者：Yusuke Kobayashi、Mami Kuroda、Natsuki Toba、Mari Okada、Rie Tanaka、Tetsutaro Kimachi

  DOI：10.1021/ol202760c

  日期：2011.12.2

  An efficient method for constructing quinoxalinone-N-oxides from cyanoacetanilides has been developed. This transformation can be achieved using inexpensive reagents and molecular oxygen under mild conditions, thus offering a practical pathway to quinoxalinone-containing pharmaceuticals such as ataquimast and opaviraline.