(4,4',5'-trichloro-5-(dimethylamino)-1'H-1,3'-bipyrrole-2,2'-diyl)bis((2-hydroxyphenyl)methanone) | 1228032-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4,4',5'-trichloro-5-(dimethylamino)-1'H-1,3'-bipyrrole-2,2'-diyl)bis((2-hydroxyphenyl)methanone)
• 英文别名: [4-chloro-1-[4,5-dichloro-2-(2-hydroxybenzoyl)-1H-pyrrol-3-yl]-5-(dimethylamino)pyrrol-2-yl]-(2-hydroxyphenyl)methanone
• CAS: 1228032-23-2
• 化学式: C₂₄H₁₈Cl₃N₃O₄
• 分子量: 518.784
• InChiKey: PKXYKWIMINEQKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  98.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  marinopyrrole F 、 二甲胺 以 四氢呋喃 为溶剂， 反应 48.0h， 以100%的产率得到(4,4',5'-trichloro-5-(dimethylamino)-1'H-1,3'-bipyrrole-2,2'-diyl)bis((2-hydroxyphenyl)methanone)
  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