(2S)-5-hydroxy-2-(1'-hydroxy-4'-oxo-cyclohexyl)-6,7-dimethoxy-2,3-dihydro-4H-chromen-4-one | 1522365-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2S)-5-hydroxy-2-(1'-hydroxy-4'-oxo-cyclohexyl)-6,7-dimethoxy-2,3-dihydro-4H-chromen-4-one
• CAS: 1522365-79-2
• 化学式: C₁₇H₂₀O₇
• 分子量: 336.342
• InChiKey: MOESEMNWTBZVQN-ZDUSSCGKSA-N

反应信息

• 作为产物：
  描述：

  (2S,1'R)-5-hydroxy-2-(1'-hydroxy-4'-oxo-cyclohex-2'-en-1'-yl)-6,7-dimethoxy-2,3-dihydro-4H-chromen-4-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、506.66 kPa 条件下， 反应 4.0h， 以90%的产率得到(2S)-5-hydroxy-2-(1'-hydroxy-4'-oxo-cyclohexyl)-6,7-dimethoxy-2,3-dihydro-4H-chromen-4-one
  参考文献：
  名称：

  Cytotoxic non-aromatic B-ring flavanones from Piper carniconnectivum C. DC.

  摘要：

  The EtOAc extract from the leaves of Piper carniconnectivum C. DC. was subjected to chromatographic separation to afford two non-aromatic B-ring flavanone compounds: 5-hydroxy-2-(1'-hydroxy-4'-oxo-cyclohex-2'-en-1'-yl)-6,7-dimethoxy-2,3-dihydro-4H-chromen-4-one (1) and 5-hydroxy-2-(1',2'-dihydroxy-4'-oxo-cyclohexyl)-6,7-dimethoxy-2,3-dihydro-4H-chromen-4-one (2). The absolute configuration of (+)-1 was unambiguously determined as 2S,1'R by electronic circular dichroism (ECD) spectroscopy and comparison to simulated spectra that were calculated using time-dependent density functional theory (TDDFT). This methodology allowed the assignment of the absolute configuration of (+)-2 also as 2S,1'R, except for the stereogenic center at C-2', which was assigned as R because of the evidence drawn from high resolution NMR experiments. The cytotoxic activity of both compounds and 3 (hydrogenated B-ring derivative of 1) was evaluated on twelve human leukemia cell lines, and the IC50 values (<10 mu M) indicated the activity of 1 against seven cell lines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.10.012