(S)-benzyl vinyl sulfoxide

• 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: (S)-benzyl vinyl sulfoxide
• 英文别名: [(S)-ethenylsulfinyl]methylbenzene
• 化学式: C₉H₁₀OS
• 分子量: 166.244
• InChiKey: SMWJPJLZIVEXKQ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二苄基二硫 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 C₅₄H₅₀O₄P₂ 、 氢气 、 双氧水 、 sodium hydroxide 作用下， 以 二氯甲烷 、 环己烷 、 水 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 1.92h， 生成 (S)-benzyl vinyl sulfoxide 、 (S)- ((ethylsulfinyl)methyl)benzene
  参考文献：
  名称：

  Hydrogenative Kinetic Resolution of Vinyl Sulfoxides

  摘要：

  Enantiopure sulfoxides are valuable precursors of organosulfur compounds with broad application in organic and pharmaceutical chemistry. An unprecedented strategy for obtaining highly enantioenriched sulfoxides based on a hydrogenative kinetic resolution using Rh-complexes of phosphine-phosphite ligands as catalysts is reported. After optimization, highly efficient conditions for the kinetic resolution of racemic sulfoxides have been identified. This methodology has been applied to a set of racemic aralkyl or aryl vinyl sulfoxides and allowed the isolation of both recovered and reduced products in excellent yields and enantioselectivities (up to 99% and 97% ee, respectively; 16 examples).

  DOI：

  10.1021/acs.orglett.5b02139

文献信息

• Hydrogenative Kinetic Resolution of Vinyl Sulfoxides
  作者：Joan R. Lao、Héctor Fernández-Pérez、Anton Vidal-Ferran

  DOI：10.1021/acs.orglett.5b02139

  日期：2015.8.21

  Enantiopure sulfoxides are valuable precursors of organosulfur compounds with broad application in organic and pharmaceutical chemistry. An unprecedented strategy for obtaining highly enantioenriched sulfoxides based on a hydrogenative kinetic resolution using Rh-complexes of phosphine-phosphite ligands as catalysts is reported. After optimization, highly efficient conditions for the kinetic resolution of racemic sulfoxides have been identified. This methodology has been applied to a set of racemic aralkyl or aryl vinyl sulfoxides and allowed the isolation of both recovered and reduced products in excellent yields and enantioselectivities (up to 99% and 97% ee, respectively; 16 examples).