2-cyano-N-methyl-N-(4-nitrophenyl)acetamide | 1040067-89-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-cyano-N-methyl-N-(4-nitrophenyl)acetamide
• CAS: 1040067-89-7
• 化学式: C₁₀H₉N₃O₃
• mdl: MFCD11184882
• 分子量: 219.2
• InChiKey: RITBPLGKOXESEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyano-N-methyl-N-(4-nitrophenyl)acetamide 在 硫酸 、 sodium nitrite 作用下， 以 乙腈 为溶剂， 以41%的产率得到3,4-dihydro-4-methyl-7-nitro-3-oxoquinoxaline-2-carbonitrile-1-oxide
  参考文献：
  名称：

  Highly Efficient Synthesis of Quinoxalinone-N-oxide via Tandem Nitrosation/Aerobic Oxidative C–N Bond Formation

  摘要：

  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.

  DOI：

  10.1021/ol202760c
• 作为产物：
  描述：

  吉非替尼中间体3 、 N-甲基对硝基苯胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-cyano-N-methyl-N-(4-nitrophenyl)acetamide
  参考文献：
  名称：

  Highly Efficient Synthesis of Quinoxalinone-N-oxide via Tandem Nitrosation/Aerobic Oxidative C–N Bond Formation

  摘要：

  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.

  DOI：

  10.1021/ol202760c

文献信息

• A diversity-oriented synthesis of caroverine derivatives via TEMPO-promoted aerobic oxidative CN bond formation
  作者：Yusuke Kobayashi、Yusuke Suzuki、Tokutaro Ogata、Tetsutaro Kimachi、Yoshiji Takemoto

  DOI：10.1016/j.tetlet.2014.03.061

  日期：2014.5

  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.