methyl (1R,2R,3R,3aR,9aR)-1,8-dihydroxy-3-methyl-9-oxo-2-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxy-2,3,3a,9a-tetrahydrocyclopenta[b]chromene-1-carboxylate | 1358786-53-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: methyl (1R,2R,3R,3aR,9aR)-1,8-dihydroxy-3-methyl-9-oxo-2-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxy-2,3,3a,9a-tetrahydrocyclopenta[b]chromene-1-carboxylate
• CAS: 1358786-53-4
• 化学式: C₂₅H₂₃F₃O₉
• 分子量: 524.447
• InChiKey: SKGGCLQDGZDVBM-ZLVPGBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (-)-preussochromone D 、 (R)-methoxytrifluoromethylphenylacetyl chloride 以 pyridine-d₅ 为溶剂， 反应 5.0h， 以0.5 mg的产率得到methyl (1R,2R,3R,3aR,9aR)-1,8-dihydroxy-3-methyl-9-oxo-2-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxy-2,3,3a,9a-tetrahydrocyclopenta[b]chromene-1-carboxylate
  参考文献：
  名称：

  A Thiopyranchromenone and Other Chromone Derivatives from an Endolichenic Fungus, Preussia africana

  摘要：

  The first example of a naturally occurring thiopyranchromenone, preussochromone A (1), and five other new chromone derivatives, preussochromones B-F (2-6), were isolated from solid cultures of an endolichenic fungus, Preussia africana. The structures of 1-6 were established primarily by NMR experiments, and 2 and 4 were further confirmed by X-ray crystallography. The absolute configurations of 1 and 2 were determined by the application of electronic circular dichroism (ECD), whereas those of C-5 in 3, C-6 in 4, and the 6,7-diol in 5 were deduced via the CD data of the in situ formed [Rh-2(OCOCF3)(4)] complex, the modified Mosher method, and Snatzke's method, respectively. Compounds 1 and 3 showed significant cytotoxicity against A549 cells.

  DOI：

  10.1021/np2009362