(R1R2RS)-2-p-tolylsulfinylcyclohexanol | 104792-01-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R1R2RS)-2-p-tolylsulfinylcyclohexanol
• 英文别名: (R1S2RS)-2-p-tolylsulfinylcyclohexanol；(S1S2RS)-2-p-tolylsulfinylcyclohexanol；(S1R2RS)-2-p-tolylsulfinylcyclohexanol；2-(Toluene-4-sulfinyl)-cyclohexanol
• CAS: 104792-01-0；111466-40-1；116049-65-1；116049-66-2；116049-67-3；116049-68-4；116257-81-9；116257-82-0；116257-83-1；116257-84-2
• 化学式: C₁₃H₁₈O₂S
• 分子量: 238.351
• InChiKey: NQEMHDDYIOYJSI-BSBHGOPBSA-N

物化性质

• 沸点：
  425.0±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R1R2RS)-2-p-tolylsulfinylcyclohexanol 在 sodium hydroxide 、 sodium acetate 作用下， 生成 (1S)-2-(4-methylphenyl)sulfanylcyclohex-2-en-1-ol
  参考文献：
  名称：

  Behaviour of 2-p-tolylsulfinyl cyclohexanols under the pummerer reaction conditions

  摘要：

  The reactions of the chiral 2-p-tolylsulfinyl cyclohexanols with Ac2O/NaOAc (or (CF3CO)2O/Py) at r.t. yielded the 2-p-tolylsulfenyl-2-cyclohexenyl acetates, which cannot be hydrolyzed into the alpha-hydroxyketones. The 1-methyl-2-p-tolylsulfinylcyclohexanols evolved with (CF3CO)2O/Py into the 3-methyl-2-p-tolylsulfenyl-2-cyclohexenyl trifluoroacetates, the latter resulting from a very highly stereoselective hetero-Claisen rearrangement (e.e. > 97%) of the initially formed 1-methyl-2-p-tolylsulfenyl-2-cyclohexenyl trifluoroacetates.

  DOI：

  10.1016/s0957-4166(00)80203-7
• 作为产物：
  描述：

  环己酮 在 bromomagnesium diisopropylamide 、 二异丁基氢化铝 作用下， 生成 (R1R2RS)-2-p-tolylsulfinylcyclohexanol
  参考文献：
  名称：

  Behaviour of 2-p-tolylsulfinyl cyclohexanols under the pummerer reaction conditions

  摘要：

  The reactions of the chiral 2-p-tolylsulfinyl cyclohexanols with Ac2O/NaOAc (or (CF3CO)2O/Py) at r.t. yielded the 2-p-tolylsulfenyl-2-cyclohexenyl acetates, which cannot be hydrolyzed into the alpha-hydroxyketones. The 1-methyl-2-p-tolylsulfinylcyclohexanols evolved with (CF3CO)2O/Py into the 3-methyl-2-p-tolylsulfenyl-2-cyclohexenyl trifluoroacetates, the latter resulting from a very highly stereoselective hetero-Claisen rearrangement (e.e. > 97%) of the initially formed 1-methyl-2-p-tolylsulfenyl-2-cyclohexenyl trifluoroacetates.

  DOI：

  10.1016/s0957-4166(00)80203-7