pacificanone B | 1016901-17-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: pacificanone B
• 英文别名: (2R,3S,4R,6S)-6-ethyl-3-hydroxy-3-[(1E,3E,5S,6R)-6-hydroxy-3,5-dimethylocta-1,3-dienyl]-2,4-dimethylcyclohexan-1-one
• CAS: 1016901-17-9
• 化学式: C₂₀H₃₄O₃
• 分子量: 322.488
• InChiKey: JSPPQWVTDRBUIB-BUQRBMCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  pacificanone B 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Salinipyrones and Pacificanones, Mixed-Precursor Polyketides from the Marine Actinomycete Salinispora pacifica

  摘要：

  Chemical examination of a phylogenetically unique strain of the obligate marine actinomycete Salinispora pacifica led to the discovery of four new polyketides, salinipyrones A and B (1, 2) and pacificanones A and B (3, 4). These compounds appear to be derived from a mixed-precursor polyketide biosynthesis involving acetate, propionate, and butyrate building blocks. Spectral analysis, employing NMR, IR, UV, and CD methods and chemical derivatization, was used to assign the structures and absolute configurations of these new metabolites. Salinipyrones A and B displayed exactly opposite CD spectra, indicating their pseudoenantiomeric relationship. This relationship was shown to be a consequence of the geometric isomerization of one double bond. The phenomenon of polyketide module skipping is proposed to explain the unusual biosynthesis of the salinipyrones and the pacificanones.

  DOI：

  10.1021/np0705155