(S₁,S₂,R_S)-1-methyl-2-p-tolylsulfinyl cyclohexanol | 135682-13-2

• 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: (S₁,S₂,R_S)-1-methyl-2-p-tolylsulfinyl cyclohexanol
• 英文别名: (1S,2S,(S)R)-1-metil-2-p-tolilsulfinilciclohexan-1-ol；(1S,2S)-1-methyl-2-[(R)-(4-methylphenyl)sulfinyl]cyclohexan-1-ol
• CAS: 135682-13-2
• 化学式: C₁₄H₂₀O₂S
• 分子量: 252.378
• InChiKey: MCQJCFFFBPTEDC-ZQIUZPCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (S₁,S₂,R_S)-1-methyl-2-p-tolylsulfinyl cyclohexanol 、 三氟乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以76%的产率得到(-)-(S)-3-methyl-2-p-tolylsulfenyl-2-cyclohexenyl trifluoroacetate
  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：

  4-Methyl-benzenesulfinic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 在 bromomagnesium diisopropylamide 作用下， 生成 (S₁,S₂,R_S)-1-methyl-2-p-tolylsulfinyl cyclohexanol
  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

• Bueno, Ana B.; Carreno, M. Carmen; Ruano, Jose L. Garcia, Anales de Quimica, 1994, vol. 90, # 7-8, p. 442 - 451
  作者：Bueno, Ana B.、Carreno, M. Carmen、Ruano, Jose L. Garcia

  DOI：——

  日期：——
• Reactions of chiral 2-p-tolylsulfinycycloalkanones with AlMe3
  作者：Ana B Bueno、M Carmen Carreño、Jean Fischer、J.L García Ruano、Begoña Peña、Lorenzo Peñas、Almudena Rubio

  DOI：10.1016/s0040-4039(00)79719-x

  日期：1991.7

  The reactions of (S2,Rs) and (R2,Rs)-2-p-tolylsulfinylcyclohexanones with AlMe3/ZnCl2 only yield the cyclohexylmethylcarbinols with R configuration at hydroxylic carbon. The (R1,S2,Rs)-1-methyl-2-p-tolylsulfinylcyclopentanol was the only compound obtained in the reaction of Me3Al with both epimeric 2-p-tolylsulfinylcyclopentanones. The d.e. of both reactions are higher than 96%.