(+/-)-(E)-(3R,R_S)-1-(phenylsulfinyl)-1-hexen-3-ol

• 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: (+/-)-(E)-(3R,R_S)-1-(phenylsulfinyl)-1-hexen-3-ol
• 英文别名: (E,3R)-1-[(R)-phenylsulfinyl]hex-1-en-3-ol
• 化学式: C₁₂H₁₆O₂S
• 分子量: 224.324
• InChiKey: PDEQJPRAXZRIRV-KYNPEBHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-(E)-(3R,R_S)-1-(phenylsulfinyl)-1-hexen-3-ol 在 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 4 A molecular sieve 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (+/-)-(2R,3R,1'R)-3-(1'-tert-butyldimethylsilyloxy-n-butyl)-2-(phenylsulfonyl)oxirane
  参考文献：
  名称：

  Nucleophilic Epoxidation of γ-Hydroxyvinyl Sulfoxide Derivatives

  摘要：

  The nucleophilic epoxidation of simple (gamma-silyloxy)vinyl sulfoxides takes place with complete stereocontrol and high yields. For substrates bearing an additional substituent at the gamma position, a reinforcing/nonreinforcing scenario is operative. While E and Z silylated substrates undergo a primarily sulfur directed epoxidation with good to excellent diastereocontrol, the related (E)-(2-methoxyethoxy)methyl ethers display diminished selectivity for the diastereomer derived from the nonreinforcing scenario.

  DOI：

  10.1021/jo0342828
• 作为产物：
  描述：

  trans-1-phenylthio-2,3-epoxyhexane 在 sodium hydroxide 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (+/-)-(E)-(3R,R_S)-1-(phenylsulfinyl)-1-hexen-3-ol
  参考文献：
  名称：

  Nucleophilic Epoxidation of γ-Hydroxyvinyl Sulfoxide Derivatives

  摘要：

  The nucleophilic epoxidation of simple (gamma-silyloxy)vinyl sulfoxides takes place with complete stereocontrol and high yields. For substrates bearing an additional substituent at the gamma position, a reinforcing/nonreinforcing scenario is operative. While E and Z silylated substrates undergo a primarily sulfur directed epoxidation with good to excellent diastereocontrol, the related (E)-(2-methoxyethoxy)methyl ethers display diminished selectivity for the diastereomer derived from the nonreinforcing scenario.

  DOI：

  10.1021/jo0342828

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.
• Nucleophilic Epoxidation of γ-Hydroxyvinyl Sulfoxide Derivatives
  作者：Roberto Fernández de la Pradilla、María Victoria Buergo、Pilar Manzano、Carlos Montero、Julián Priego、Alma Viso、Félix H. Cano、María Paz Martínez-Alcázar

  DOI：10.1021/jo0342828

  日期：2003.6.1

  The nucleophilic epoxidation of simple (gamma-silyloxy)vinyl sulfoxides takes place with complete stereocontrol and high yields. For substrates bearing an additional substituent at the gamma position, a reinforcing/nonreinforcing scenario is operative. While E and Z silylated substrates undergo a primarily sulfur directed epoxidation with good to excellent diastereocontrol, the related (E)-(2-methoxyethoxy)methyl ethers display diminished selectivity for the diastereomer derived from the nonreinforcing scenario.