(5S,1''S,2''R)-5-(4'-<2'',3''-dihydroxy-1''-methylpropyl>phenyl)-2-cyclohexenone | 155907-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (5S,1''S,2''R)-5-(4'-<2'',3''-dihydroxy-1''-methylpropyl>phenyl)-2-cyclohexenone
• CAS: 155907-17-8
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: MOLHGRHSOPXCMT-PJODQICGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5S,1''S,2''R)-5-(4'-<2'',3''-dihydroxy-1''-methylpropyl>phenyl)-2-cyclohexenone 在 palladium on activated charcoal ruthenium trichloride 、 sodium periodate 、 氢气 作用下， 以 四氯化碳 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 2.75h， 生成 (2S,1''S)-2-(4'-<3''-oxocyclohexyl>phenyl)propanoic acid
  参考文献：
  名称：

  Enantioselective synthesis of the four isomers of the biologically active metabolite of the 2-arylpropanoic acid NSAID, ximoprofen, and assessment of their inhibitory activity on human platelet cyclo-oxygenase in vitro

  摘要：

  The four stereoisomers of the parent keto acid of the oximino drug ximoprofen have been prepared in high enantiomeric purity. The stereochemistry in the propionic acid chain was established by the combination of Sharpless epoxidation followed by stereoselective hydrogenolysis of the benzylic carbon-oxygen bond with inversion of configuration. The stereochemistry of the centre in the cyclohexanone ring was controlled by the stereoselective conjugate addition of the arylpropanoic acid moiety to the enantiomers of 5-(trimethylsilyl)-2-cyclohexenone with subsequent removal of the trimethylsilyl group. The pharmacological activity of each of the four isomers of the keto acid parent of ximoprofen were assessed by their in vitro inhibition of human platelet cyclo-oxygenase. As expected, the (S) configuration of the propionic acid chain was essential for activity but it was also found that the stereochemistry in the cyclohexanone moiety was important. Attempts to separate the (E) and (Z) isomers of the oxime derivative from one of the stereoisomers were unsuccessful.

  DOI：

  10.1016/0957-4166(95)00443-2
• 作为产物：
  描述：

  (3R,5S,1'S,4''R)-3-(4-<1'-<2'',2''-dimethyl-1,3-dioxolan-4''-yl>ethyl>phenyl)-5-(trimethylsilyl)cyclohexanone 在 盐酸 、 copper dichloride 作用下， 生成 (5S,1''S,2''R)-5-(4'-<2'',3''-dihydroxy-1''-methylpropyl>phenyl)-2-cyclohexenone
  参考文献：
  名称：

  Enantioselective synthesis of the four isomers of the biologically active metabolite of the 2-arylpropanoic acid NSAID, ximoprofen, and assessment of their inhibitory activity on human platelet cyclo-oxygenase in vitro

  摘要：

  The four stereoisomers of the parent keto acid of the oximino drug ximoprofen have been prepared in high enantiomeric purity. The stereochemistry in the propionic acid chain was established by the combination of Sharpless epoxidation followed by stereoselective hydrogenolysis of the benzylic carbon-oxygen bond with inversion of configuration. The stereochemistry of the centre in the cyclohexanone ring was controlled by the stereoselective conjugate addition of the arylpropanoic acid moiety to the enantiomers of 5-(trimethylsilyl)-2-cyclohexenone with subsequent removal of the trimethylsilyl group. The pharmacological activity of each of the four isomers of the keto acid parent of ximoprofen were assessed by their in vitro inhibition of human platelet cyclo-oxygenase. As expected, the (S) configuration of the propionic acid chain was essential for activity but it was also found that the stereochemistry in the cyclohexanone moiety was important. Attempts to separate the (E) and (Z) isomers of the oxime derivative from one of the stereoisomers were unsuccessful.

  DOI：

  10.1016/0957-4166(95)00443-2