(2R,3S)-2-<(methylsulfonyl)methyl>-3-propyloxirane

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: (2R,3S)-2-<(methylsulfonyl)methyl>-3-propyloxirane
• 英文别名: (2R,3S)-2-(methylsulfonylmethyl)-3-propyloxirane
• 化学式: C₇H₁₄O₃S
• 分子量: 178.252
• InChiKey: WKFUGKRHNUGZCW-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-<(methylsulfonyl)methyl>-3-propyloxirane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以68%的产率得到(3S)-(E)-1-(methylsulfonyl)hex-1-en-3-ol
  参考文献：
  名称：

  Homochiral 2,3-epoxy sulfides—powerful new synthetic building blocks providing stereoselective access to 2,3-epoxy sulfoxides, 2,3-dihydroxy sulfoxides and (E)-γ-hydroxy-α,β-unsaturated sulfoxides and sulfones. X-Ray molecular structure of rac-(2R*,3R*)-1-[(S*)-phenylsulfinyl] hexane-2,3-diol

  摘要：

  The stereoselective transformation of homochiral 2,3-epoxy sulfoxides into 2,3-epoxy sulfoxides is described. These intermediates undergo elimination under basic reaction conditions to give (E)-gamma-hydroxy-alpha,beta-unsaturated sulfoxides, and under Lewis acidic conditions form novel cyclic sulfoxonium salts which on hydrolysis give 2,3-dihydroxy sulfoxides with excellent stereochemical control. 2,3-Dihydroxy sulfoxides can also be converted into (E)-gamma-hydroxy-alpha,beta-unsaturated sulfoxides by elimination via a cyclic sulfite. The synthesis of (E)-gamma-hydroxy-alpha,beta-unsaturated sulfones by base-catalysed elimination of a 2,3-epoxy sulfone is also described.

  DOI：

  10.1039/p19950000847
• 作为产物：
  描述：

  (2R,3S)-2-<(methylsulfanyl)methyl>-3-propyloxirane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以88%的产率得到(2R,3S)-2-<(methylsulfonyl)methyl>-3-propyloxirane
  参考文献：
  名称：

  Homochiral 2,3-epoxy sulfides—powerful new synthetic building blocks providing stereoselective access to 2,3-epoxy sulfoxides, 2,3-dihydroxy sulfoxides and (E)-γ-hydroxy-α,β-unsaturated sulfoxides and sulfones. X-Ray molecular structure of rac-(2R*,3R*)-1-[(S*)-phenylsulfinyl] hexane-2,3-diol

  摘要：

  The stereoselective transformation of homochiral 2,3-epoxy sulfoxides into 2,3-epoxy sulfoxides is described. These intermediates undergo elimination under basic reaction conditions to give (E)-gamma-hydroxy-alpha,beta-unsaturated sulfoxides, and under Lewis acidic conditions form novel cyclic sulfoxonium salts which on hydrolysis give 2,3-dihydroxy sulfoxides with excellent stereochemical control. 2,3-Dihydroxy sulfoxides can also be converted into (E)-gamma-hydroxy-alpha,beta-unsaturated sulfoxides by elimination via a cyclic sulfite. The synthesis of (E)-gamma-hydroxy-alpha,beta-unsaturated sulfones by base-catalysed elimination of a 2,3-epoxy sulfone is also described.

  DOI：

  10.1039/p19950000847

文献信息

• Homochiral 2,3-epoxy sulfides—powerful new synthetic building blocks providing stereoselective access to 2,3-epoxy sulfoxides, 2,3-dihydroxy sulfoxides and (E)-γ-hydroxy-α,β-unsaturated sulfoxides and sulfones. X-Ray molecular structure of rac-(2R*,3R*)-1-[(S*)-phenylsulfinyl] hexane-2,3-diol
  作者：Andrew D. Westwell、Mark Thornton-Pett、Christopher M. Rayner

  DOI：10.1039/p19950000847

  日期：——

  The stereoselective transformation of homochiral 2,3-epoxy sulfoxides into 2,3-epoxy sulfoxides is described. These intermediates undergo elimination under basic reaction conditions to give (E)-gamma-hydroxy-alpha,beta-unsaturated sulfoxides, and under Lewis acidic conditions form novel cyclic sulfoxonium salts which on hydrolysis give 2,3-dihydroxy sulfoxides with excellent stereochemical control. 2,3-Dihydroxy sulfoxides can also be converted into (E)-gamma-hydroxy-alpha,beta-unsaturated sulfoxides by elimination via a cyclic sulfite. The synthesis of (E)-gamma-hydroxy-alpha,beta-unsaturated sulfones by base-catalysed elimination of a 2,3-epoxy sulfone is also described.