(2R,3R)-1-<(S)-phenylsulfinyl>hexane-2,3-diol | 156041-91-7

• 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: (2R,3R)-1-<(S)-phenylsulfinyl>hexane-2,3-diol
• 英文别名: (2R,3R)-1-[(S)-phenylsulfinyl]hexane-2,3-diol
• CAS: 156041-91-7
• 化学式: C₁₂H₁₈O₃S
• 分子量: 242.339
• InChiKey: DCSDPOJQQJRWHY-WQGACYEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1-<(S)-phenylsulfinyl>hexane-2,3-diol 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (4S,5S)-4-((S)-Benzenesulfinylmethyl)-5-propyl-[1,3,2]dioxathiolane 2-oxide
  参考文献：
  名称：

  Homochiral 2,3-epoxy sulfides as precursors to -γ-hydroxy-α,β-unsaturated sulfoxides and sulfones.

  摘要：

  The synthesis of E-gamma-hydroxy-alpha,beta-unsaturated sulfoxides and sulfones from the corresponding homochiral 2,3-epoxy sulfides is described with excellent control of double bond geometry and stereochemistry at both the sulfoxide and secondary alcohol chiral centres.

  DOI：

  10.1016/s0957-4166(00)86205-9
• 作为产物：
  描述：

  (2R,3S)-2-<(phenylsulfinyl)methyl>-3-propyloxirane 在 三氟化硼乙醚 、 碳酸氢钠 作用下， 生成 (2R,3S)-2-<(S)-(phenylsulfinyl)methyl>-3-propyloxirane 、 (2R,3R)-1-<(S)-phenylsulfinyl>hexane-2,3-diol
  参考文献：
  名称：

  Homochiral 2,3-epoxy sulfides as precursors to -γ-hydroxy-α,β-unsaturated sulfoxides and sulfones.

  摘要：

  The synthesis of E-gamma-hydroxy-alpha,beta-unsaturated sulfoxides and sulfones from the corresponding homochiral 2,3-epoxy sulfides is described with excellent control of double bond geometry and stereochemistry at both the sulfoxide and secondary alcohol chiral centres.

  DOI：

  10.1016/s0957-4166(00)86205-9

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.
• Homochiral 2,3-epoxy sulfides as precursors to -γ-hydroxy-α,β-unsaturated sulfoxides and sulfones.
  作者：Andrew D. Westwell、Christopher M. Rayner

  DOI：10.1016/s0957-4166(00)86205-9

  日期：1994.3

  The synthesis of E-gamma-hydroxy-alpha,beta-unsaturated sulfoxides and sulfones from the corresponding homochiral 2,3-epoxy sulfides is described with excellent control of double bond geometry and stereochemistry at both the sulfoxide and secondary alcohol chiral centres.