N-methyl-N-phenyl-(4-nitrophenyl)acetamide | 31733-79-6

• 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: N-methyl-N-phenyl-(4-nitrophenyl)acetamide
• 英文别名: N-(4-Nitro-phenylacetyl)-N-methyl-anilin；N-methyl-2-(4-nitrophenyl)-N-phenylacetamide
• CAS: 31733-79-6
• 化学式: C₁₅H₁₄N₂O₃
• 分子量: 270.288
• InChiKey: HJASLCYXTYYESP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methyl-N-phenyl-(4-nitrophenyl)acetamide 在 ferrous(II) sulfate heptahydrate 、 水 作用下， 以 甲醇 、 硝基甲烷 、 2,2,2-三氟乙醇 为溶剂， 反应 0.69h， 生成 4-imino-1'-methyl-1'H-spiro[cyclohexane-1,4'-quinoline]-2,5-dien-2'(3'H)-one 2,2,2-trifluoroacetate
  参考文献：
  名称：

  高价碘（III）介导的芳胺氧化脱芳香化环化

  摘要：

  AbstractAn oxidative dearomatizing cyclization of arylamines promoted by iodobenzene bis(trifluoroacetate) [PhI(CF3CO2)2] has been explored, leading to a novel synthetic approach to functionalized spirocyclic building blocks containing the structurally unique dieniminium moiety. This unprecedented methodology, featuring oxidative dearomatization and carbon‐carbon bond‐forming cyclization, to some extent, not only expands the synthetic potential of hypervalent iodine chemistry, but also enriches the oxidation chemistry of arylamines.magnified image

  DOI：

  10.1002/adsc.201400191
• 作为产物：
  描述：

  对硝基苯乙酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 N-methyl-N-phenyl-(4-nitrophenyl)acetamide
  参考文献：
  名称：

  高价碘（III）介导的芳胺氧化脱芳香化环化

  摘要：

  AbstractAn oxidative dearomatizing cyclization of arylamines promoted by iodobenzene bis(trifluoroacetate) [PhI(CF3CO2)2] has been explored, leading to a novel synthetic approach to functionalized spirocyclic building blocks containing the structurally unique dieniminium moiety. This unprecedented methodology, featuring oxidative dearomatization and carbon‐carbon bond‐forming cyclization, to some extent, not only expands the synthetic potential of hypervalent iodine chemistry, but also enriches the oxidation chemistry of arylamines.magnified image

  DOI：

  10.1002/adsc.201400191

文献信息

• Vicarious nucleophilic substitution of hydrogen proceeding via heterocyclic ring opening
  作者：Mieczyslaw Ma̧kosza、Michal Sypniewski、Tomasz Glinka

  DOI：10.1016/0040-4020(95)01104-8

  日期：1996.2

  Carbanions of five-membered S-heterocycles react with nitroarenes via the ring-opening VNS reaction or oxidative nucleophilic substitution of hydrogen. The reaction course is affected by rigidity of the ring.

  五元S杂环的碳负离子会通过开环VNS反应或氢的氧化亲核取代反应与硝基芳烃反应。反应过程受环的刚度影响。
• Irreversible enzyme inhibitors. 197. Water-soluble reversible inhibitors of dihydrofolate reductase with potent antitumor activity derived from 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-phenyl-s-triazine
  作者：B. R. Baker、Wallace T. Ashton

  DOI：10.1021/jm00261a009

  日期：1973.3
• Hypervalent Iodine(III)-Mediated Oxidative Dearomatizing Cyclization of Arylamines
  作者：Cong-Yang Jin、Ji-Yuan Du、Chao Zeng、Xian-He Zhao、Ye-Xing Cao、Xiang-Zhi Zhang、Xin-Yun Lu、Chun-An Fan

  DOI：10.1002/adsc.201400191

  日期：2014.8.11

  AbstractAn oxidative dearomatizing cyclization of arylamines promoted by iodobenzene bis(trifluoroacetate) [PhI(CF3CO2)2] has been explored, leading to a novel synthetic approach to functionalized spirocyclic building blocks containing the structurally unique dieniminium moiety. This unprecedented methodology, featuring oxidative dearomatization and carbon‐carbon bond‐forming cyclization, to some extent, not only expands the synthetic potential of hypervalent iodine chemistry, but also enriches the oxidation chemistry of arylamines.magnified image