6-styrylpyran-2-one | 1208-97-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-styrylpyran-2-one
• 英文别名: 6-styryl-2-pyrone；6--pyron-(2)；6-Styryl-2h-pyran-2-one；6-(2-phenylethenyl)pyran-2-one
• CAS: 1208-97-5
• 化学式: C₁₃H₁₀O₂
• 分子量: 198.221
• InChiKey: PJQXIFKFVCLVQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-styrylpyran-2-one 以 水 为溶剂， 生成 goniotamirenone A
  参考文献：
  名称：

  Styryllactones from Goniothalamus tamirensis

  摘要：

  The phytochemical investigation of the twig and leaf extracts of Goniothalamus tamirensis led to the isolation and identification of 15 compounds including three rare previously undescribed styryllactones, goniotamirenones A-C, together with 12 known compounds. (Z)-6-Styryl-5,6-dihydro-2-pyranone and 5-(1-hydroxy-3-phenyl-allyl)dihydro-furan-2-one are reported here for the first time as previously undescribed natural products. Their structures were elucidated by spectroscopic methods. Goniotamirenone A was synthesized via a [2 + 2] cycloaddition reaction of 6-styrrylpyran-2-one in quantitative yield. The absolute configurations of goniotamirenones B and C were identified from experimental and calculated ECD data, while the absolute configurations of (-)-5-acetoxygoniothalamin, (-)-isoaltholactone, parvistone E, and 5-(1-hydroxy-3-phenyl-allyl)-dihydro-furan-2-one were identified by single-crystal X-ray diffraction analysis using Cu K alpha radiation. The absolute configurations of the other related compounds were determined from comparisons of their ECD spectra with relevant compounds reported in the literature. (-)-5-Acetoxygoniothalamin exhibited potent cytotoxicity against the colon cancer cell line (HCT116) with an IC50 value of 8.6 mu M which was better than the standard control (doxorubicin, IC50 = 9.7 mu M), while (Z)-6-styry1-5,6-dihydro-2-pyranone was less active with an IC50 value of 22.1 mu M.

  DOI：

  10.1016/j.phytochem.2019.112248