3-hydroxy-3,4-dimethylpentyl p-methoxyphenyl sulfide | 150666-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-hydroxy-3,4-dimethylpentyl p-methoxyphenyl sulfide
• 英文别名: 1-(4-Methoxyphenyl)sulfanyl-3,4-dimethylpentan-3-ol
• CAS: 150666-76-5
• 化学式: C₁₄H₂₂O₂S
• 分子量: 254.393
• InChiKey: JXYPPGHGIORUQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  54.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3,4-dimethylpentyl p-methoxyphenyl sulfide 在 氧气 、 rose bengal 作用下， 以 丙酮 为溶剂， 以56%的产率得到3-hydroxy-3,4-dimethylpentyl p-methoxyphenyl sulfone
  参考文献：
  名称：

  Remote participation during photooxidation at sulfur. Evidence for sulfurane intermediates

  摘要：

  The photooxidations of geminally substituted gamma-hydroxy sulfides results in formation of unusual oxidative elimination products. Detailed spectral data and the independent synthesis of a close analogue provide compelling evidence for the structures of these olefins. The formation of the olefins is attributed to decomposition of sulfurane intermediates. This conclusion is supported by a detailed kinetic study which separated the chemical, k(r), and physical, k(q), components to the overall deactivation of singlet oxygen. Those sulfides with the best geometry for sulfide-hydroxyl interaction are also the substrates which react most rapidly with singlet oxygen to give oxidation products. In addition, sulfone yields are in excess of 50% for the hydroxy-substituted sulfides but less than 5% for their hydrocarbon analogues. Several mechanisms that provide explanations for these unusually high sulfone yields are presented.

  DOI：

  10.1021/jo00042a031