(2S,3R,3aS,5R,6S,7aS)-6-methoxy-3-phenyl-2-(phenylselanylmethyl)-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-5-ol | 1054809-57-2

• 分子结构分类: 有机化合物
• 英文名称: (2S,3R,3aS,5R,6S,7aS)-6-methoxy-3-phenyl-2-(phenylselanylmethyl)-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-5-ol
• CAS: 1054809-57-2
• 化学式: C₂₂H₂₆O₃Se
• 分子量: 417.407
• InChiKey: NJDUXSAYLAYVTR-OGVIVNNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R,3aS,5R,6S,7aS)-6-methoxy-3-phenyl-2-(phenylselanylmethyl)-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-5-ol 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以7.5 mg的产率得到(2R,3R,3aS,5R,6S,7aS)-6-methoxy-2-methyl-3-phenyl-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-5-ol
  参考文献：
  名称：

  Neoflavonoids and Related Constituents from Nepalese Propolis and Their Nitric Oxide Production Inhibitory Activity

  摘要：

  A methanolic extract of Nepalese propolis yielded 10 new open-chain neoflavonoids (1-10), a new chalcone (11), and eight previously reported compounds (12-19). Their structures were determined on the basis of spectroscopic data and chemical conversion. The isolated compounds other than 5, 8, and 16 showed dose-dependent inhibitory activities on nitric oxide production in lipopolysaccharide-activated macrophage-like J774.1 cells and were more active than a positive control, N-G-monomethyl-L-arginine (IC50, 27.1 mu M). The most potent activities, of 6 and 7 (IC50, 0.5 mu M), were greater than another positive control, caffeic acid phenethyl ester (IC50, 4.8 mu M).

  DOI：

  10.1021/np050009k
• 作为产物：
  描述：

  (1R,2S,4S,5S)-2-methoxy-5-[(1R)-1-phenyl-2-propenyl]-1,4-cyclohexanediol 、 苯基氯化硒 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以17.2 mg的产率得到(2S,3R,3aS,5R,6S,7aS)-6-methoxy-3-phenyl-2-(phenylselanylmethyl)-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-5-ol
  参考文献：
  名称：

  Neoflavonoids and Related Constituents from Nepalese Propolis and Their Nitric Oxide Production Inhibitory Activity

  摘要：

  A methanolic extract of Nepalese propolis yielded 10 new open-chain neoflavonoids (1-10), a new chalcone (11), and eight previously reported compounds (12-19). Their structures were determined on the basis of spectroscopic data and chemical conversion. The isolated compounds other than 5, 8, and 16 showed dose-dependent inhibitory activities on nitric oxide production in lipopolysaccharide-activated macrophage-like J774.1 cells and were more active than a positive control, N-G-monomethyl-L-arginine (IC50, 27.1 mu M). The most potent activities, of 6 and 7 (IC50, 0.5 mu M), were greater than another positive control, caffeic acid phenethyl ester (IC50, 4.8 mu M).

  DOI：

  10.1021/np050009k