(4,5-dichloro-3-iodo-1H-pyrrol-2-yl)(2-hydroxyphenyl)methanone | 117598-09-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4,5-dichloro-3-iodo-1H-pyrrol-2-yl)(2-hydroxyphenyl)methanone
• 英文别名: C-3-iodo-monodeoxypyoluteorin；(4,5-dichloro-3-iodo-1H-pyrrol-2-yl)-(2-hydroxyphenyl)methanone
• CAS: 117598-09-1
• 化学式: C₁₁H₆Cl₂INO₂
• 分子量: 381.985
• InChiKey: GAWMCIIYJQIJMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  [2-(4,5-dichloro-3-iodo-1H-pyrrole-2-carbonyl)phenyl] acetate 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以94%的产率得到(4,5-dichloro-3-iodo-1H-pyrrol-2-yl)(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