ethyl 4-nitro-1-(3-cyanopropyl)pyrrole-2-carboxylate | 1575816-22-6

• 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: ethyl 4-nitro-1-(3-cyanopropyl)pyrrole-2-carboxylate
• 英文别名: Ethyl 1-(3-cyanopropyl)-4-nitropyrrole-2-carboxylate
• CAS: 1575816-22-6
• 化学式: C₁₁H₁₃N₃O₄
• 分子量: 251.242
• InChiKey: RMVFQLJMCCRZDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-nitro-1-(3-cyanopropyl)pyrrole-2-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以78%的产率得到4-nitro-1-(3-cyanopropyl)pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Orthogonally Positioned Diamino Pyrrole- and Imidazole-Containing Polyamides: Synthesis of 1-(3-Substituted-propyl)-4-nitropyrrole-2-carboxylic Acid and 1-(3-Chloropropyl)-4-nitroimidazole-2-carboxylic Acid

  摘要：

  Pyrrole- and imidazole-containing polyamides can be tailored to recognize the DNA 6-8 base pair sequence. We found that adding a second amino group via the N1-position of pyrrole or imidazole in polyamides could enhance their DNA binding affinity and water solubility while retaining sequence specificity. Synthesis of the key 1-substituted-4-nitropyrrole (and imidazole)-2-carboxylic acid building blocks are described. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.839795
• 作为产物：
  描述：

  4-硝基吡咯-2-羧酸乙酯 、 4-溴丁腈 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以99%的产率得到ethyl 4-nitro-1-(3-cyanopropyl)pyrrole-2-carboxylate
  参考文献：
  名称：

  Orthogonally Positioned Diamino Pyrrole- and Imidazole-Containing Polyamides: Synthesis of 1-(3-Substituted-propyl)-4-nitropyrrole-2-carboxylic Acid and 1-(3-Chloropropyl)-4-nitroimidazole-2-carboxylic Acid

  摘要：

  Pyrrole- and imidazole-containing polyamides can be tailored to recognize the DNA 6-8 base pair sequence. We found that adding a second amino group via the N1-position of pyrrole or imidazole in polyamides could enhance their DNA binding affinity and water solubility while retaining sequence specificity. Synthesis of the key 1-substituted-4-nitropyrrole (and imidazole)-2-carboxylic acid building blocks are described. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.839795