6-nitro-5-ethoxycarbonylbenzofuran | 1131538-81-2

• 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: 6-nitro-5-ethoxycarbonylbenzofuran
• CAS: 1131538-81-2
• 化学式: C₁₁H₉NO₅
• 分子量: 235.196
• InChiKey: OYIVYDOYDWKFJT-UHFFFAOYSA-N

物化性质

• 沸点：
  346.6±22.0 °C(predicted)
• 密度：
  1.362±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  82.58
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-(2-硝基乙烯基)呋喃 、 (E)-ethyl 3-nitroacrylate 在 三氯化铝 作用下， 以 xylene 为溶剂， 反应 2.0h， 生成 4-nitro-5-ethoxycarbonylbenzofuran 、 6-nitro-5-ethoxycarbonylbenzofuran 、 4,6-dinitro-5-ethoxycarbonyl-4,5,6,7-tetrahydrobenzofuran 、 ethyl benzo[b]furan-5-carboxylate
  参考文献：
  名称：

  Reaction of alkyl-3-nitro-and-3-bromo-3-nitroacrylates with 2-(2-nitroethenyl)furan

  摘要：

  The diene condensation of beta-nitro and beta-bromo-beta-nitroacrylates with 2-(2-nitroethenyl)furan as 1,3-diene leads to a mixture of regioisomeric tetrahydrobenzofurans transforming under the reaction conditions into benzofurancarboxylates due to the easy dehydrohalogenation, denitration, and dehydration. In the case of a gem-bromonitroacrylate reaction takes two routes: diene synthesis and alkylation of the furan ring, the latter process prevailing. The structure of products formed was established by spectral methods. The investigation of geometry of 2-(1-methoxycarbonyl-2-nitroethenyl)-5-(2-nitroethenyl)furan by XRD analysis showed that its vinyl fragments have the coplanar chelate-like structure with the cisoid orientation of the CO2Me and NO2 groups. The ester group deviates from the plane of the the carbon-carbon multiple bond.

  DOI：

  10.1134/s1070363208050216