ethyl 4'-cyano-4-nitro[1,1'-biphenyl]-2-carboxylate | 835916-54-6

• 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: ethyl 4'-cyano-4-nitro[1,1'-biphenyl]-2-carboxylate
• 英文别名: Ethyl 4a(2)-cyano-4-nitro[1,1a(2)-biphenyl]-2-carboxylate；ethyl 2-(4-cyanophenyl)-5-nitrobenzoate
• CAS: 835916-54-6
• 化学式: C₁₆H₁₂N₂O₄
• 分子量: 296.282
• InChiKey: GNGBSBONADQGET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-碘苯甲酸乙酯, 在 硫酸 、 苯基氯化镁 、 硝酸 作用下， 以 四氢呋喃 为溶剂， 反应 14.25h， 生成 ethyl 4'-cyano-4-nitro[1,1'-biphenyl]-2-carboxylate
  参考文献：
  名称：

  Synthesis of Functionalized Nitroarylmagnesium Halides via an Iodine−Magnesium Exchange

  摘要：

  Various nitro-substituted aryl and heteroaryl iodides undergo an iodine-magnesium exchange reaction when treated with PhMgCl leading to nitro-containing magnesium organometallics. These Grignard reagents display an excellent stability at temperatures below -40 degrees C and do not undergo electron-transfer reactions. They react as expected with various electrophiles.

  DOI：

  10.1021/jo048132o

文献信息

• Synthesis of Nitro-Substituted Polyfunctional Biphenyls by Negishi Cross-Coupling ofo-Nitroarylzinc Reagents
  作者：Ioannis Sapountzis、Henry Dube、Paul Knochel

  DOI：10.1002/adsc.200303235

  日期：2004.6

  iodine-magnesium exchange reaction allows the preparation of polyfunctional arylmagnesium species bearing a nitro group in the ortho-position. After transmetalation to the corresponding arylzinc compound, these organometallics undergo a palladium-catalyzed Negishi cross-coupling with various aryl iodides to provide polyfunctional biphenyls bearing nitro groups in moderate to good yields.

  碘-镁交换反应允许制备在邻位带有硝基的多官能芳基镁物质。在金属转移成相应的芳基锌化合物后，这些有机金属与各种芳基碘化物进行钯催化的Negishi交叉偶联，以中等至良好的产率提供带有硝基的多官能联苯。
• Synthesis of Functionalized Nitroarylmagnesium Halides via an Iodine−Magnesium Exchange
  作者：Ioannis Sapountzis、Henry Dube、Robert Lewis、Nina Gommermann、Paul Knochel

  DOI：10.1021/jo048132o

  日期：2005.4.1

  Various nitro-substituted aryl and heteroaryl iodides undergo an iodine-magnesium exchange reaction when treated with PhMgCl leading to nitro-containing magnesium organometallics. These Grignard reagents display an excellent stability at temperatures below -40 degrees C and do not undergo electron-transfer reactions. They react as expected with various electrophiles.