(3S,5S)-3-(4'-methylbenzenethio)-5-(trimethylsilyl)cyclohexanone | 116498-72-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3S,5S)-3-(4'-methylbenzenethio)-5-(trimethylsilyl)cyclohexanone
• 英文别名: (5R)-trans-3-p-tolylthio-5-(trimethylsilyl)cyclohexanone；(+)-3-p-tolylthio-5-(trimethylsilyl)cyclohexanone；(3S,5S)-3-(4-methylphenyl)sulfanyl-5-trimethylsilylcyclohexan-1-one
• CAS: 116498-72-7
• 化学式: C₁₆H₂₄OSSi
• 分子量: 292.517
• InChiKey: DBMNNWLCXPBYPJ-HOTGVXAUSA-N

物化性质

• 沸点：
  388.8±42.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,5S)-3-(4'-methylbenzenethio)-5-(trimethylsilyl)cyclohexanone 在 sodium hydroxide 、 disodium hydrogenphosphate 、 N-氯代丁二酰亚胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成
  参考文献：
  名称：

  Construction of chiral quarternary carbon centers using 3-substituted-5-trimethylsilyl-2-cyclohexenones: Synthesis of (+)−∝-cuparenone

  摘要：

  DOI：

  10.1016/s0040-4039(00)80086-6
• 作为产物：
  描述：

  5-trimethylsilyl-2-cyclohexanone 、 4-甲苯硫酚 、 辛可尼丁 以50%的产率得到
  参考文献：
  名称：

  ASAOKA, MORIO;SHIMA, KUNIHISA;TAKEI, HISASHI, TETRAHEDRON LETT., 28,(1987) N 46, 5669-5672

  摘要：

  DOI：

文献信息

• Synthesis of (+)-α-curcumene, (+)-curcumone, and (-)-methyl citronellate starting from optically pure 5-trimethylsilyl-2-cyclohexenone
  作者：Morio Asaoka、Kunihisa Shima、Naoaki Fujii、Hisashi Takei

  DOI：10.1016/s0040-4020(01)86178-0

  日期：1988.1
• (R)- and (S)-5-trimethylsilyl-2-cyclohexenone: a versatile chiral source for the synthesis of optically active cyclohexanone derivatives
  作者：Morio Asaoka、Kunihisa Shima、Hisashi Takei

  DOI：10.1016/s0040-4039(00)96809-6

  日期：1987.1
• 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.