(S)-3-Methyl-2-p-tolylsulfanyl-cyclohex-2-enol | 140710-37-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (S)-3-Methyl-2-p-tolylsulfanyl-cyclohex-2-enol
• 英文别名: (1S)-3-methyl-2-(4-methylphenyl)sulfanylcyclohex-2-en-1-ol
• CAS: 140710-37-8
• 化学式: C₁₄H₁₈OS
• 分子量: 234.362
• InChiKey: XDASKQXNBVDYOM-ZDUSSCGKSA-N

物化性质

• 沸点：
  382.0±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (-)-(S)-3-methyl-2-p-tolylsulfenyl-2-cyclohexenyl trifluoroacetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以84%的产率得到(S)-3-Methyl-2-p-tolylsulfanyl-cyclohex-2-enol
  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

文献信息

• Asymmetric synthesis of cyclohex-2-enols: The examples of seudenol and analogues
  作者：Ana B. Bueno、M. Carmen Carreño、JoséL. García Ruano、Chafiq Hamdouchi

  DOI：10.1016/0957-4166(95)00152-f

  日期：1995.6

  An efficient Synthesis of enantiomerically pure cyclohex-2-enols from the reaction of 2-p-tolylsulfinyl cyclohexanols with (CF3CO)(2)O/Py and subsequent hydrogenolysis of the C-S bond with Li/Naphthalene, is reported. This strategy has been applied to the asymmetric synthesis of seudenol and 1-methylcyclohex-2-en-1-ol. New data on the rearrangement of the trifluoroacetate group when 2-p-tolylsulfinyl-1-methylcyclohexenols are treated under the Pummerer reaction conditions are also reported.