5-nitro-2-(2-nitroethenyl)furan | 830-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-nitro-2-(2-nitroethenyl)furan
• 英文别名: 1-nitro-2-(5-nitrofuran-2-yl)ethene；2-nitro-5-(2-nitroethenyl)furan
• CAS: 830-07-9
• 化学式: C₆H₄N₂O₅
• 分子量: 184.108
• InChiKey: NMZDNQIJZAERIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-nitro-2-(2-nitroethenyl)furan 在 溴 、 potassium acetate 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 25.25h， 生成 4-[2-bromo-2-nitro-1-(5-nitrofuran-2-yl)ethyl]morpholine
  参考文献：
  名称：

  Furan-containing gem-bromonitroethenes: Synthesis and reaction with morpholine

  摘要：

  The first time the representative of furan-containing gem-bromonitroethenes 5-nitro-2-(2-bromo-2-nitro-ethenyl)furan was synthesized by bromination of 5-nitro-2-(2-nitroethenyl)furan followed by dehydrohalogenation of the dibromide. Morpholine adducts of the synthesized beta-substituted gem-bromonitroethene and its analog with a 5-bromo-2-furyl substituent were obtained. The structures of the gem-bromonitroethenes and aza adducts were characterized by spectral methods (IR, UV, H-1, and C-13-{H-1} NMR, including H-1-C-13 HMQC and HMBC).

  DOI：

  10.1134/s1070363215060110

文献信息

• Ionic liquid-promoted stereoselective [3 + 2] cycloaddition of 1-hetaryl-2-nitroethenes to azomethine imines generated in situ
  作者：Mikhail I. Pleshchev、Margarita A. Epishina、Vadim V. Kachala、Vladimir V. Kuznetsov、Alexander S. Goloveshkin、Ivan S. Bushmarinov、Nina N. Makhova

  DOI：10.1016/j.mencom.2013.07.009

  日期：2013.7

  Ionic liquids facilitate regio- and stereoselective [3+2] cycloaddition of 1-hetaryl-2-nitroethenes to azomethine imines generated catalytically from 6-Ar-1,5-diazabicyclo[3.1.0]hexanes in the presence of BF3 center dot Et2O. The similar reaction is possible in MeCN only for azomethine imine with Ar = 2,4-(MeO)(2)C6H3 to give a mixture of two diastereomers.
• Furan-containing gem-bromonitroethenes: Synthesis and reaction with morpholine
  作者：S. S. Eliseenko、S. V. Makarenko、V. M. Berestovitskaya

  DOI：10.1134/s1070363215060110

  日期：2015.6

  The first time the representative of furan-containing gem-bromonitroethenes 5-nitro-2-(2-bromo-2-nitro-ethenyl)furan was synthesized by bromination of 5-nitro-2-(2-nitroethenyl)furan followed by dehydrohalogenation of the dibromide. Morpholine adducts of the synthesized beta-substituted gem-bromonitroethene and its analog with a 5-bromo-2-furyl substituent were obtained. The structures of the gem-bromonitroethenes and aza adducts were characterized by spectral methods (IR, UV, H-1, and C-13-H-1} NMR, including H-1-C-13 HMQC and HMBC).