(+/-)-(E)-(3S,R_S)-1-(phenylsulfinyl)-1-hexen-3-ol methoxyethoxymethyl ether

• 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)-(3S,R_S)-1-(phenylsulfinyl)-1-hexen-3-ol methoxyethoxymethyl ether
• 英文别名: [(R)-[(E,3S)-3-(2-methoxyethoxymethoxy)hex-1-enyl]sulfinyl]benzene
• 化学式: C₁₆H₂₄O₄S
• 分子量: 312.43
• InChiKey: QAOMZFQSEGYNEP-WOEFOLRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-(E)-(3S,R_S)-1-(phenylsulfinyl)-1-hexen-3-ol methoxyethoxymethyl ether 在 叔丁基过氧化氢 、 4 A molecular sieve 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 生成 (+/-)-(2S,3S,1'S,S_S)-3-(1'-methoxyethoxymethoxy-n-butyl)-2-(phenylsulfinyl)oxirane 、 (+/-)-(2R,3R,1'S,S_S)-3-(1'-methoxyethoxymethoxy-n-butyl)-2-(phenylsulfinyl)oxirane 、 (+/-)-(2SR,3SR,1'S)-3-(1'-methoxyethoxymethoxy-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 4-二甲氨基吡啶 、 sodium hydroxide 、 potassium carbonate 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (+/-)-(E)-(3S,R_S)-1-(phenylsulfinyl)-1-hexen-3-ol methoxyethoxymethyl ether
  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

• 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.