1-epi-acremine F | 1448507-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-epi-acremine F
• 英文别名: (1R,2R,4S)-5-[(E)-3-hydroxy-3-methylbut-1-enyl]-2-methylcyclohex-5-ene-1,2,4-triol
• CAS: 1448507-19-4
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: KLZSJMCXTDLPSF-VYWVJKCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  acremine A 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以2 mg的产率得到acremine F
  参考文献：
  名称：

  Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum

  摘要：

  This study reports the isolation and characterization of six new acremine metabolites, 5-chloroacremine A (4), 5-chloroacremine H (5), and acremines 0 (6), P (7), Q(8), and R (9), together with the known acremines A (1), F (2), and N (3) from the fungus Acremonium persicinum cultured from the marine sponge Anomoianthella rubra. The relative configuration of acremine F (2) was determined by analyses of proton coupling constant values and NOESY data, and the absolute configuration confirmed as (IS, 4S, 6R) by X-ray crystallographic analysis of the borate ester derivative 15. Acremines O, P, and R were each shown to be of 8R configuration by H-1 NMR analyses of MPA esters. The relative configurations suggested for acremines P and Q were each deduced by molecular modeling together with NOESY and coupling constant data. The (3)J(H-C) values in acremine P were measured using the pulse sequence EXSIDE, and the observed (3)J(H8-C4) of 5.4 Hz and small (3)J(H-C) values (<1.5 Hz) from H-8 to C-10 and C-11 were fully consistent with stereoisomer 7a. For acremine Q NOESY data combined with molecular modeling established the preferred diastereomer 8a.

  DOI：

  10.1021/np4002114