methyl 2-(4-nitrophenyl)azocarboxylate | 13444-01-4

• 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: methyl 2-(4-nitrophenyl)azocarboxylate
• 英文别名: methyl p-nitrophenylazoformate；(4-nitro-phenyl)-diazenecarboxylic acid methyl ester；(4-Nitro-phenyl)-diazencarbonsaeure-methylester；(4-Nitro-phenylazo)-ameisensaeure-methylester；p-Nitro-phenyl-diazencarbonsaeure-methylester；p-Nitro-phenylazo-carbonsaeure-methylester；methyl N-(4-nitrophenyl)iminocarbamate
• CAS: 13444-01-4
• 化学式: C₈H₇N₃O₄
• 分子量: 209.161
• InChiKey: FJVTUVRXJPFHOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  96.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-nitrophenyl)azocarboxylate 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Formation of cinnoline derivatives by a gold(I)-catalyzed hydroarylation of N-propargyl-N′-arylhydrazines

  摘要：

  A study concerning the gold(I)-catalyzed hydroarylation of N-propargyl-N'-arylhydrazinecarboxylic acid methyl esters is described. The use of the gold complex [XPhosAu(NCCH(3))SbF(6)] as the catalyst in refluxing nitromethane allows the generally rapid and efficient synthesis of a range of functionalized 4-exo-methylene-1,2-dihydrocinnolines. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.06.017
• 作为产物：
  描述：

  N-[(4-硝基苯基)氨基]氨基甲酸甲酯 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2-(4-nitrophenyl)azocarboxylate
  参考文献：
  名称：

  Formation of cinnoline derivatives by a gold(I)-catalyzed hydroarylation of N-propargyl-N′-arylhydrazines

  摘要：

  A study concerning the gold(I)-catalyzed hydroarylation of N-propargyl-N'-arylhydrazinecarboxylic acid methyl esters is described. The use of the gold complex [XPhosAu(NCCH(3))SbF(6)] as the catalyst in refluxing nitromethane allows the generally rapid and efficient synthesis of a range of functionalized 4-exo-methylene-1,2-dihydrocinnolines. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.06.017

文献信息

• Nucleophilic Substitutions and Radical Reactions of Phenylazocarboxylates
  作者：Hannelore Jasch、Sarah B. Höfling、Markus R. Heinrich

  DOI：10.1021/jo202406k

  日期：2012.2.3

  Nucleophilic substitutions of the benzene ring proceed with aromatic amines and alcohols under mild conditions. The attack of aliphatic amines may be directed to the aromatic core as well as to the carbonyl unit leading to azocarboxamides. The benzene ring can further be modified through radical reactions, in which the tert-butyloxycarbonylazo group enables the generation of aryl radicals at either elevated

  苯基偶氮羧酸叔丁酯是合成有机化学的多功能构建基块。苯环的亲核取代是在温和条件下用芳族胺和醇进行的。脂族胺的攻击可以直接针对芳族核以及导致偶氮羧酰胺的羰基单元。苯环可通过自由基反应进一步改性，其中叔丁氧基羰基偶氮基团能够在升高的温度或在酸性条件下生成芳基。自由基反应包括氧合，卤化，碳卤化，碳羟基化和芳基-芳基偶联。
• Longo, Gazzetta Chimica Italiana, 1933, vol. 63, p. 463,466
  作者：Longo

  DOI：——

  日期：——
• Formation of cinnoline derivatives by a gold(I)-catalyzed hydroarylation of N-propargyl-N′-arylhydrazines
  作者：Igor Dias Jurberg、Fabien Gagosz

  DOI：10.1016/j.jorganchem.2010.06.017

  日期：2011.1

  A study concerning the gold(I)-catalyzed hydroarylation of N-propargyl-N'-arylhydrazinecarboxylic acid methyl esters is described. The use of the gold complex [XPhosAu(NCCH(3))SbF(6)] as the catalyst in refluxing nitromethane allows the generally rapid and efficient synthesis of a range of functionalized 4-exo-methylene-1,2-dihydrocinnolines. (C) 2010 Elsevier B.V. All rights reserved.