(2S,4R,5S)-4-hydroxy-5-methoxy-2-[(1S)-1-phenyl-2-propenyl]-cyclohexanone | 857906-70-8

• 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: (2S,4R,5S)-4-hydroxy-5-methoxy-2-[(1S)-1-phenyl-2-propenyl]-cyclohexanone
• 英文别名: (2S,4R,5S)-4-hydroxy-5-methoxy-2-[(1R)-1-phenylprop-2-enyl]cyclohexan-1-one
• CAS: 857906-70-8
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: XFQZPZFTYDDJIR-UGQVUOCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4R,5S)-4-hydroxy-5-methoxy-2-[(1S)-1-phenyl-2-propenyl]-cyclohexanone 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以22.6 mg的产率得到(1R,2S,4S,5S)-2-methoxy-5-[(1R)-1-phenyl-2-propenyl]-1,4-cyclohexanediol
  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