(2S,1''R)-2-<4'-(3''-oxocyclohexyl)phenyl>propanoic acid | 155907-24-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S,1''R)-2-<4'-(3''-oxocyclohexyl)phenyl>propanoic acid
• 英文别名: (2S,1''R)-2-(4'-<3''-oxocyclohexyl>phenyl)propanoic acid；(2S)-2-[4-[(1R)-3-oxocyclohexyl]phenyl]propanoic acid
• CAS: 155907-24-7
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: FASVODQCERZDFX-GXFFZTMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S,1''R)-2-<4'-(3''-oxocyclohexyl)phenyl>propanoic acid 在 盐酸羟胺 作用下， 以 吡啶 为溶剂， 生成 (S)-2-(4-{(R)-3-[(E)-Hydroxyimino]-cyclohexyl}-phenyl)-propionic acid
  参考文献：
  名称：

  Concerning the enantioselective synthesis of the isomers of the arylpropanoic acid NSAID ximoprofen

  摘要：

  All four stereoisomers of the parent ketone of the oximido drug ximoprofen have been prepared pure. An attempt to isolate the pure E and Z isomers of the oxime derivative from one of these stereoisomers was unsuccessful.

  DOI：

  10.1016/s0040-4039(00)79970-9
• 作为产物：
  描述：

  (R)-(-)-5-trimethylsilyl-2-cyclohexenone 在 ruthenium trichloride 、 palladium on activated charcoal 盐酸 、 甲醇 、 potassium fluoride 、 sodium periodate 、 copper(I) bromide dimethylsulfide complex 、 氢气 、 magnesium 、 copper dichloride 作用下， 以 甲醇 为溶剂， 生成 (2S,1''R)-2-<4'-(3''-oxocyclohexyl)phenyl>propanoic acid
  参考文献：
  名称：

  Concerning the enantioselective synthesis of the isomers of the arylpropanoic acid NSAID ximoprofen

  摘要：

  All four stereoisomers of the parent ketone of the oximido drug ximoprofen have been prepared pure. An attempt to isolate the pure E and Z isomers of the oxime derivative from one of these stereoisomers was unsuccessful.

  DOI：

  10.1016/s0040-4039(00)79970-9

文献信息

• 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
  作者：David P.G. Hamon、Peter J. Hayball、Ralph A. Massy-Westropp、Josephine L. Newton、Julie G. Tamblyn

  DOI：10.1016/0957-4166(95)00443-2

  日期：1996.1

  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.
• Hamon David P. G., Massy-Westropp Ralph A., Newton Josephine L., Tetrahedron Lett, 35 (1994) N 7, S 1079-1082
  作者：Hamon David P. G., Massy-Westropp Ralph A., Newton Josephine L.

  DOI：——

  日期：——