N-[3-[2-amino-4-[(E)-1-(2-amino-1H-imidazol-5-yl)-3-[(4,5-dibromo-1H-pyrrole-2-carbonyl)amino]prop-1-enyl]-1H-imidazol-5-yl]propyl]-4,5-dibromo-1H-pyrrole-2-carboxamide | 1433132-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[3-[2-amino-4-[(E)-1-(2-amino-1H-imidazol-5-yl)-3-[(4,5-dibromo-1H-pyrrole-2-carbonyl)amino]prop-1-enyl]-1H-imidazol-5-yl]propyl]-4,5-dibromo-1H-pyrrole-2-carboxamide
• CAS: 1433132-02-5
• 化学式: C₂₂H₂₂Br₄N₁₀O₂
• 分子量: 778.098
• InChiKey: RNISWAUJGXDYCK-YCRREMRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  199
• 氢给体数：
  8
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲酸 、 N-[3-[2-amino-4-[(E)-1-(2-amino-1H-imidazol-5-yl)-3-[(4,5-dibromo-1H-pyrrole-2-carbonyl)amino]prop-1-enyl]-1H-imidazol-5-yl]propyl]-4,5-dibromo-1H-pyrrole-2-carboxamide 在 10% palladium hydroxide on charcoal 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 以63%的产率得到debromonagelamide D
  参考文献：
  名称：

  Unprecedented Biomimetic Homodimerization of Oroidin and Clathrodin Marine Metabolites in the Presence of HMPA or Phosphonate Salt Tweezers

  摘要：

  The first biomimetic homodimerization of oroidin and clathrodin was effected in the presence HMPA and diphosphonate salts, strong guanidinium and amide chelating agents. The intermolecular associations probably interfere with the entropically and kinetically favored intramolecular cyclizations. Use of oroidin.1/2HCl salt or clathrodin.1/2HCl was indicative in the presence of the ambident nucleophilic and electrophilic tautomers of the 2-aminoimidazolic oroidin and clathrodin precursors. Surprisingly, the homodimerization of oroidin led to the nagelamide D skeleton, while the homodimerization of clathrodin gave the benzene para-symmetrical structure 19. The common process was rationalized from tautomeric precursors I and III.

  DOI：

  10.1021/np400048r

文献信息

• Unprecedented Biomimetic Homodimerization of Oroidin and Clathrodin Marine Metabolites in the Presence of HMPA or Phosphonate Salt Tweezers
  作者：Clarisse Lejeune、Hua Tian、Jérôme Appenzeller、Ludmila Ermolenko、Marie-Thérèse Martin、Ali Al-Mourabit

  DOI：10.1021/np400048r

  日期：2013.5.24

  The first biomimetic homodimerization of oroidin and clathrodin was effected in the presence HMPA and diphosphonate salts, strong guanidinium and amide chelating agents. The intermolecular associations probably interfere with the entropically and kinetically favored intramolecular cyclizations. Use of oroidin.1/2HCl salt or clathrodin.1/2HCl was indicative in the presence of the ambident nucleophilic and electrophilic tautomers of the 2-aminoimidazolic oroidin and clathrodin precursors. Surprisingly, the homodimerization of oroidin led to the nagelamide D skeleton, while the homodimerization of clathrodin gave the benzene para-symmetrical structure 19. The common process was rationalized from tautomeric precursors I and III.