cis-3-butyl-2-<(phenylthio)methyl>cyclohexanone | 143144-74-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: cis-3-butyl-2-<(phenylthio)methyl>cyclohexanone
• 英文别名: (2S,3S)-3-butyl-2-(phenylsulfanylmethyl)cyclohexan-1-one
• CAS: 143144-74-5
• 化学式: C₁₇H₂₄OS
• 分子量: 276.443
• InChiKey: MUBKYKCOHJMUJN-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  cis-3-butyl-2-<(phenylthio)methyl>cyclohexanone 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以28%的产率得到(2R,3S)-3-Butyl-2-phenylsulfanylmethyl-cyclohexanone
  参考文献：
  名称：

  Stereoselective synthesis of cis 2,3-disubstituted cycloheptanones by kinetic protonation

  摘要：

  The hitherto unknown stereochemistry concerning the formation of 2,3-disubstituted cycloheptanones by the Michael addition reaction was studied. The Michael addition of thiophenol to 3-substituted 2-methylene-cycloheptanones in the presence of triethylamine in THF at ambient temperature produced 3-substituted 2-[(phenylthio)methyl]cycloheptanones with high cis selectivity (>96/4), which was unequivocally established by H-1 NMR and X-rays analyses. An isomerization experiment and theoretical calculations (AM1) suggest that the origin of the observed high stereoselectivity can be explained in terms of kinetic protonation of the corresponding enolate intermediate.

  DOI：

  10.1021/jo00044a027
• 作为产物：
  描述：

  (3S)-3-butyl-2-methylidenecyclohexan-1-one 、 苯硫酚 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 cis-3-butyl-2-<(phenylthio)methyl>cyclohexanone
  参考文献：
  名称：

  Stereoselective synthesis of cis 2,3-disubstituted cycloheptanones by kinetic protonation

  摘要：

  The hitherto unknown stereochemistry concerning the formation of 2,3-disubstituted cycloheptanones by the Michael addition reaction was studied. The Michael addition of thiophenol to 3-substituted 2-methylene-cycloheptanones in the presence of triethylamine in THF at ambient temperature produced 3-substituted 2-[(phenylthio)methyl]cycloheptanones with high cis selectivity (>96/4), which was unequivocally established by H-1 NMR and X-rays analyses. An isomerization experiment and theoretical calculations (AM1) suggest that the origin of the observed high stereoselectivity can be explained in terms of kinetic protonation of the corresponding enolate intermediate.

  DOI：

  10.1021/jo00044a027

文献信息

• Stereoselective synthesis of cis 2,3-disubstituted cycloheptanones by kinetic protonation
  作者：Rui Tamura、Kenichiro Watabe、Akio Kamimura、Kenzi Hori、Yoshinobu Yokomori

  DOI：10.1021/jo00044a027

  日期：1992.8

  The hitherto unknown stereochemistry concerning the formation of 2,3-disubstituted cycloheptanones by the Michael addition reaction was studied. The Michael addition of thiophenol to 3-substituted 2-methylene-cycloheptanones in the presence of triethylamine in THF at ambient temperature produced 3-substituted 2-[(phenylthio)methyl]cycloheptanones with high cis selectivity (>96/4), which was unequivocally established by H-1 NMR and X-rays analyses. An isomerization experiment and theoretical calculations (AM1) suggest that the origin of the observed high stereoselectivity can be explained in terms of kinetic protonation of the corresponding enolate intermediate.