methyl 5-[[5-[[N'-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamoyl]-1H-pyrrole-2-carbonyl]amino]pentanoate | 948863-37-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 5-[[5-[[N'-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamoyl]-1H-pyrrole-2-carbonyl]amino]pentanoate
• CAS: 948863-37-4
• 化学式: C₁₈H₂₇N₅O₆
• 分子量: 409.442
• InChiKey: NRNWIVHQKCDXFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-[[5-[[N'-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamoyl]-1H-pyrrole-2-carbonyl]amino]pentanoate 在 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 5-[[5-(diaminomethylidenecarbamoyl)-1H-pyrrole-2-carbonyl]amino]pentanoic acid
  参考文献：
  名称：

  Synthesis and Self-Association Properties of Flexible Guanidiniocarbonylpyrrole−Carboxylate Zwitterions in DMSO: Intra- versus Intermolecular Ion Pairing

  摘要：

  We have synthesized a new class of flexible zwitterions 6a-e, in which a carboxylate is linked via an alkyl chain with variable length (one to five methylene groups) to a guanidiniocarbonylpyrrole cation. The self-association properties of these zwitterions were determined by NMR dilution studies in DMSO and by ESI-MS experiments. The stability and hence also the size of the aggregates formed via self-assembly is critically dependent on the length and therefore flexibility of the spacer. Whereas the smallest zwitterion 6a forms large aggregates already at low concentrations, the more flexible zwitterions only form small oligomers (6b) or dimers (6c-e) at much larger concentrations. The differences between the five zwitterions can be explained based on the different extent of intramolecular ion pairing within the monomers. Any intramolecular ion pairing, which becomes possible with increasing linker length, stabilizes the monomer and therefore destabilizes any oligomer.

  DOI：

  10.1021/jo070641d
• 作为产物：
  描述：

  5-氨基颉草酸 在 N-甲基吗啉 、 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 methyl 5-[[5-[[N'-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamoyl]-1H-pyrrole-2-carbonyl]amino]pentanoate
  参考文献：
  名称：

  Synthesis and Self-Association Properties of Flexible Guanidiniocarbonylpyrrole−Carboxylate Zwitterions in DMSO: Intra- versus Intermolecular Ion Pairing

  摘要：

  We have synthesized a new class of flexible zwitterions 6a-e, in which a carboxylate is linked via an alkyl chain with variable length (one to five methylene groups) to a guanidiniocarbonylpyrrole cation. The self-association properties of these zwitterions were determined by NMR dilution studies in DMSO and by ESI-MS experiments. The stability and hence also the size of the aggregates formed via self-assembly is critically dependent on the length and therefore flexibility of the spacer. Whereas the smallest zwitterion 6a forms large aggregates already at low concentrations, the more flexible zwitterions only form small oligomers (6b) or dimers (6c-e) at much larger concentrations. The differences between the five zwitterions can be explained based on the different extent of intramolecular ion pairing within the monomers. Any intramolecular ion pairing, which becomes possible with increasing linker length, stabilizes the monomer and therefore destabilizes any oligomer.

  DOI：

  10.1021/jo070641d