14α-hydroxymarcfortine A

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌嗪基哌啶类
• 英文名称: 14α-hydroxymarcfortine A
• 英文别名: (1'S,7'R,8R,8'R,10'R)-7'-hydroxy-4,4,11',11',14'-pentamethylspiro[10H-[1,4]dioxepino[2,3-g]indole-8,12'-3,14-diazatetracyclo[6.5.2.01,10.03,8]pentadecane]-9,15'-dione
• 化学式: C₂₈H₃₅N₃O₅
• 分子量: 493.603
• InChiKey: FHAVTZCWTWSDEE-UYBSWNAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  36
• 可旋转键数：
  0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  91.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  14α-hydroxymarcfortine A 在 platinum on activated charcoal 氧气 、 间氯过氧苯甲酸 作用下， 生成 14α-hydroxy-16-oxoparaherquamide B 、 14,15-dehydro-16,17-dioxomarcfortine A
  参考文献：
  名称：

  Conversion of Marcfortine A to Paraherquamides via a Novel Platinum−Oxygen-Mediated Ring Contracting Reaction

  摘要：

  The paraherquamides and marcfortines represent a novel class of anthelmintics. The sole structural difference between marcfortine A (1) and paraherquamide A (5) occurs in ring G. By employing a ring contracting reaction utilizing platinum and oxygen (Pt/O-2) at a key point in the synthesis, we were able to directly convert marcfortine A to the intermediate 16-oxoparherquamide B (2), thereby eliminating six steps in our earlier synthesis. Paraherquamide A was also prepared from 14 alpha-hydroxymarcfortine A (3) and 14 alpha-hydroxy-14 beta-methylmarcfortine A (6) using Pt/O-2 chemistry. Additionally, parahequamide derivative 20 was synthesized from marcfortine A derivative 16.

  DOI：

  10.1021/jo971227o