diethyl 4,4',5,5'-tetrabromo-1'H-1,3'-bipyrrole-2,2'-dicarboxylate | 1228049-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: diethyl 4,4',5,5'-tetrabromo-1'H-1,3'-bipyrrole-2,2'-dicarboxylate
• 英文别名: ethyl 4,5-dibromo-1-(4,5-dibromo-2-ethoxycarbonyl-1H-pyrrol-3-yl)pyrrole-2-carboxylate
• CAS: 1228049-52-2
• 化学式: C₁₄H₁₂Br₄N₂O₄
• 分子量: 591.876
• InChiKey: JAWBAJGQIYZXNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  diethyl 1′H-[1,3′-bipyrrole]-2,2′-dicarboxylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以86%的产率得到diethyl 4,4',5,5'-tetrabromo-1'H-1,3'-bipyrrole-2,2'-dicarboxylate
  参考文献：
  名称：

  Structures, Reactivities, and Antibiotic Properties of the Marinopyrroles A−F

  摘要：

  Cultivation of actinomycete strain CNQ-418, retrieved from a deep ocean sediment sample off the coast of La Jolla, CA, has provided marinopyrroles A F. Sharing just 98% 16S rRNA gene sequence identity with S. sannurensis, the strain likely represents a new Streptomyces species. The metabolites contain an unusual 1,3'-bipyrrole core decorated with several chlorine and bromine substituents and possess marked antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). The congested N,C-biaryl bond establishes an axis of chirality that, for marinopyrroles A-E, is configurationally stable at room temperature. Moreover, the natural products are fashioned strictly in the M-configuration. The Paal-Knorr condensation was adapted for the synthesis of the 1,3'-bipyrrole core. Halogenation of this material with N-bromosuccinimide cleanly furnished the 4,4',5,5'-tetrahalogenated core that characterizes this class of marine-derived metabolites.

  DOI：

  10.1021/jo1002054

文献信息

• Structures, Reactivities, and Antibiotic Properties of the Marinopyrroles A−F
  作者：Chambers C. Hughes、Christopher A. Kauffman、Paul R. Jensen、William Fenical

  DOI：10.1021/jo1002054

  日期：2010.5.21

  Cultivation of actinomycete strain CNQ-418, retrieved from a deep ocean sediment sample off the coast of La Jolla, CA, has provided marinopyrroles A F. Sharing just 98% 16S rRNA gene sequence identity with S. sannurensis, the strain likely represents a new Streptomyces species. The metabolites contain an unusual 1,3'-bipyrrole core decorated with several chlorine and bromine substituents and possess marked antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). The congested N,C-biaryl bond establishes an axis of chirality that, for marinopyrroles A-E, is configurationally stable at room temperature. Moreover, the natural products are fashioned strictly in the M-configuration. The Paal-Knorr condensation was adapted for the synthesis of the 1,3'-bipyrrole core. Halogenation of this material with N-bromosuccinimide cleanly furnished the 4,4',5,5'-tetrahalogenated core that characterizes this class of marine-derived metabolites.