4-isopropyl-3-(phenylsulfanyl)cyclohexanone

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-isopropyl-3-(phenylsulfanyl)cyclohexanone
• 英文别名: (3S,4R)-3-phenylsulfanyl-4-propan-2-ylcyclohexan-1-one
• 化学式: C₁₅H₂₀OS
• 分子量: 248.389
• InChiKey: YHULKQALUSETCU-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  4-isopropyl-3-(phenylsulfanyl)cyclohexanone 在 Candida antarctica lipase B 、 sodium hydroxide 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 异丙醚 为溶剂， 反应 13.0h， 生成 (1R,3R,4S)-4-isopropyl-3-(phenylsulfanyl)cyclohexanol
  参考文献：
  名称：

  Enantiomerically enriched cryptone by lipase catalysed kinetic resolution

  摘要：

  Thiophenol was added to racemic cryptone (4-isopropyl-2-cyclohexene-1-one) and the resulting 1,4-addition products, cis- and trans-4-isopropyl-3-(phenyisulfanyl)cyclohexanone were separated and the latter reduced to rac-1,3-cis-1,4-trans-4-isopropyl3-(phenylsulfanyl)cyclohexanol, which was subjected to lipase catalysed resolution by acylation catalysed by CAL-B (Candida antarctica lipase B). The alcohol enantiorners obtained were oxidised. The remaining alcohol was separated from the produced acetate, which was hydrolysed to the alcohol. The initial products, probably sulfoxidoketones spontaneously decomposed to furnish enantiomerically enriched (R)- and (S)-cryptone with up to 76% and 98% ee, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.012
• 作为产物：
  描述：

  4-异丙基环己-2-烯-1-酮 、 苯硫酚 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以51%的产率得到4-isopropyl-3-(phenylsulfanyl)cyclohexanone
  参考文献：
  名称：

  Enantiomerically enriched cryptone by lipase catalysed kinetic resolution

  摘要：

  Thiophenol was added to racemic cryptone (4-isopropyl-2-cyclohexene-1-one) and the resulting 1,4-addition products, cis- and trans-4-isopropyl-3-(phenyisulfanyl)cyclohexanone were separated and the latter reduced to rac-1,3-cis-1,4-trans-4-isopropyl3-(phenylsulfanyl)cyclohexanol, which was subjected to lipase catalysed resolution by acylation catalysed by CAL-B (Candida antarctica lipase B). The alcohol enantiorners obtained were oxidised. The remaining alcohol was separated from the produced acetate, which was hydrolysed to the alcohol. The initial products, probably sulfoxidoketones spontaneously decomposed to furnish enantiomerically enriched (R)- and (S)-cryptone with up to 76% and 98% ee, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.012

文献信息

• Enantiomerically enriched cryptone by lipase catalysed kinetic resolution
  作者：Dan Isaksson、Kristina Sjödin、Hans-Erik Högberg

  DOI：10.1016/j.tetasy.2005.12.012

  日期：2006.1

  Thiophenol was added to racemic cryptone (4-isopropyl-2-cyclohexene-1-one) and the resulting 1,4-addition products, cis- and trans-4-isopropyl-3-(phenyisulfanyl)cyclohexanone were separated and the latter reduced to rac-1,3-cis-1,4-trans-4-isopropyl3-(phenylsulfanyl)cyclohexanol, which was subjected to lipase catalysed resolution by acylation catalysed by CAL-B (Candida antarctica lipase B). The alcohol enantiorners obtained were oxidised. The remaining alcohol was separated from the produced acetate, which was hydrolysed to the alcohol. The initial products, probably sulfoxidoketones spontaneously decomposed to furnish enantiomerically enriched (R)- and (S)-cryptone with up to 76% and 98% ee, respectively. (c) 2005 Elsevier Ltd. All rights reserved.