(+)-(1S,2R)-trans-2-Phenylcyclohexyl (S)-methanesulfinate | 134311-28-7

• 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: (+)-(1S,2R)-trans-2-Phenylcyclohexyl (S)-methanesulfinate
• 英文别名: [(1S,2R)-2-phenylcyclohexyl] (R)-methanesulfinate
• CAS: 134311-28-7
• 化学式: C₁₃H₁₈O₂S
• 分子量: 238.351
• InChiKey: AKSRNOQXWVOXOV-DVOMOZLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(1S,2R)-trans-2-Phenylcyclohexyl (S)-methanesulfinate 、 对甲苯基溴化镁 以 乙醚 为溶剂， 反应 1.0h， 以76%的产率得到(S)-(-)-甲基对甲苯亚砜
  参考文献：
  名称：

  Improved method for the preparation of enantiomerically pure sulfinate esters

  摘要：

  DOI：

  10.1021/jo00014a045
• 作为产物：
  描述：

  (1S,2R)-(+)-反-2-苯基-1-环己醇 在 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成 (+)-(1S,2R)-trans-2-Phenylcyclohexyl (S)-methanesulfinate
  参考文献：
  名称：

  Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane

  摘要：

  Reaction of the chiral auxiliary trans-2-phenylcyclohexanol (1) with thionyl chloride afforded a nearly equal mixture of two diastereomeric chlorosulfite esters (6); Treatment of this mixture with an equivalent amount of a dialkylzinc reagent (Me, et, i-Pr) afforded high levels of conversion of both chlorosulfite esters to (mainly) a single diastereomer of the sulfinate ester (7). Levels of absolute stereochemical induction ranged from 10:1 to 96:4 under conditions affording high chemical yields. The method was employed for the separate synthesis of both enantiomers of sulforaphane (13).

  DOI：

  10.1021/jo00082a016

文献信息

• Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane
  作者：James K. Whitesell、Man-Shing Wong

  DOI：10.1021/jo00082a016

  日期：1994.2

  Reaction of the chiral auxiliary trans-2-phenylcyclohexanol (1) with thionyl chloride afforded a nearly equal mixture of two diastereomeric chlorosulfite esters (6); Treatment of this mixture with an equivalent amount of a dialkylzinc reagent (Me, et, i-Pr) afforded high levels of conversion of both chlorosulfite esters to (mainly) a single diastereomer of the sulfinate ester (7). Levels of absolute stereochemical induction ranged from 10:1 to 96:4 under conditions affording high chemical yields. The method was employed for the separate synthesis of both enantiomers of sulforaphane (13).
• Improved method for the preparation of enantiomerically pure sulfinate esters
  作者：James K. Whitesell、Man Shing Wong

  DOI：10.1021/jo00014a045

  日期：1991.7