1,1'-(1,2-ethanediyl)bis[N-(2-carbethoxy)-4-nitro-1H-pyrrole] | 1021332-08-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1,1'-(1,2-ethanediyl)bis[N-(2-carbethoxy)-4-nitro-1H-pyrrole]
• 英文别名: Ethyl 1-[2-(2-ethoxycarbonyl-4-nitropyrrol-1-yl)ethyl]-4-nitropyrrole-2-carboxylate
• CAS: 1021332-08-0
• 化学式: C₁₆H₁₈N₄O₈
• 分子量: 394.341
• InChiKey: ZVQAAUVDHRTDNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,1'-(1,2-ethanediyl)bis[N-(2-carbethoxy)-4-nitro-1H-pyrrole] 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 1,1'-(1,2-ethanediyl)bis[N-5-[[[(3-dimethylaminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl]-4-[[[4-formylamino-1-methyl-1H-pyrrol-2-yl]carbonyl]amino]-1H-pyrrole-2-carboxamide]
  参考文献：
  名称：

  Synthesis of a C-2 Stapled Bis-Lexitropsin

  摘要：

  A convenient synthesis method was developed for the preparation of C-stapled homodimeric bis-lexitropsins connected through the nitrogen atoms of the central pyrrole ring with a bis-methylene linker. This lexitropsin is designed as a standard for other bis-lexitropsins with longer chains in biological evaluation and NMR studies. The key step in this method is the treatment of ethyl 4-nitropyrrole-2-carboxylate with flame-dried potassium carbonate in DMF followed by the addition of 1,2-dibromoethane to form the 1,2-dipyrroloethane derivative.

  DOI：

  10.1007/s00706-007-0644-z
• 作为产物：
  描述：

  4-硝基吡咯-2-羧酸乙酯 、 1,2-二溴乙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以49%的产率得到1,1'-(1,2-ethanediyl)bis[N-(2-carbethoxy)-4-nitro-1H-pyrrole]
  参考文献：
  名称：

  Synthesis of a C-2 Stapled Bis-Lexitropsin

  摘要：

  A convenient synthesis method was developed for the preparation of C-stapled homodimeric bis-lexitropsins connected through the nitrogen atoms of the central pyrrole ring with a bis-methylene linker. This lexitropsin is designed as a standard for other bis-lexitropsins with longer chains in biological evaluation and NMR studies. The key step in this method is the treatment of ethyl 4-nitropyrrole-2-carboxylate with flame-dried potassium carbonate in DMF followed by the addition of 1,2-dibromoethane to form the 1,2-dipyrroloethane derivative.

  DOI：

  10.1007/s00706-007-0644-z

文献信息

• Synthesis of a C-2 Stapled Bis-Lexitropsin
  作者：Naim H. Al-Said、Sami Klaib

  DOI：10.1007/s00706-007-0644-z

  日期：2007.6

  A convenient synthesis method was developed for the preparation of C-stapled homodimeric bis-lexitropsins connected through the nitrogen atoms of the central pyrrole ring with a bis-methylene linker. This lexitropsin is designed as a standard for other bis-lexitropsins with longer chains in biological evaluation and NMR studies. The key step in this method is the treatment of ethyl 4-nitropyrrole-2-carboxylate with flame-dried potassium carbonate in DMF followed by the addition of 1,2-dibromoethane to form the 1,2-dipyrroloethane derivative.