ethyl 3-bromo-2-(1H-indol-3-yl)-3-nitropropanoate | 1128070-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 3-bromo-2-(1H-indol-3-yl)-3-nitropropanoate
• CAS: 1128070-86-9
• 化学式: C₁₃H₁₃BrN₂O₄
• 分子量: 341.161
• InChiKey: IJYGYXABWMZYNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  458.4±45.0 °C(predicted)
• 密度：
  1.588±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-bromo-2-(1H-indol-3-yl)-3-nitropropanoate 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 2.5h， 以55%的产率得到ethyl 2-(1H-indol-3-yl)-3-nitroacrylate
  参考文献：
  名称：

  α-Indolyl-β-nitroacrylates. Synthesis and structure

  摘要：

  A one-pot procedure has been developed for the synthesis of alpha-indolyl-beta-nitroacrylates by reaction of beta-bromo-beta-nitroacrilates with indole and substituted indoles. All indolylnitroacrilates thus obtained have Z configuration of the double bond. According to the X-ray diffraction data, ethyl 2-(1-methyl-1H-indol-3-yl)-3-nitroacrylate is characterized by s-trans conformation of the double C=C bond and indole ring; its crystal packing involves intermolecular hydrogen bonds C-H center dot center dot center dot O and C-H center dot center dot center dot pi with formation of centrosymmetric dimers which give rise to bilayer supramolecular structures.

  DOI：

  10.1134/s1070363208050228
• 作为产物：
  描述：

  吲哚 、 ethyl 3-bromo-3-nitroacrylate 以 苯 为溶剂， 以84%的产率得到ethyl 3-bromo-2-(1H-indol-3-yl)-3-nitropropanoate
  参考文献：
  名称：

  α-Indolyl-β-nitroacrylates. Synthesis and structure

  摘要：

  A one-pot procedure has been developed for the synthesis of alpha-indolyl-beta-nitroacrylates by reaction of beta-bromo-beta-nitroacrilates with indole and substituted indoles. All indolylnitroacrilates thus obtained have Z configuration of the double bond. According to the X-ray diffraction data, ethyl 2-(1-methyl-1H-indol-3-yl)-3-nitroacrylate is characterized by s-trans conformation of the double C=C bond and indole ring; its crystal packing involves intermolecular hydrogen bonds C-H center dot center dot center dot O and C-H center dot center dot center dot pi with formation of centrosymmetric dimers which give rise to bilayer supramolecular structures.

  DOI：

  10.1134/s1070363208050228