ethyl p-fluorophenyl sulfoxide | 144488-63-1

• 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: ethyl p-fluorophenyl sulfoxide
• 英文别名: (R)-ethyl (p-F)-phenyl sulfoxide；1-[(R)-ethylsulfinyl]-4-fluorobenzene
• CAS: 144488-63-1
• 化学式: C₈H₉FOS
• 分子量: 172.223
• InChiKey: HMNZWRINAXKQRI-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-fluorophenyl vinyl sulfide 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 C₅₄H₅₀O₄P₂ 、 氢气 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 环己烷 为溶剂， -78.0~20.0 ℃ 、500.01 kPa 条件下， 反应 0.5h， 生成 (S)-(p-F)-phenyl vinyl sulfoxide 、 ethyl p-fluorophenyl sulfoxide
  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

• Effects of substrate structure on the enantioselectivity and stereochemical course of sulfoxidation catalyzed by cyclohexanone monooxygenase
  作者：Glacomo Carrea、Barbara Redigolo、Sergio Riva、Stefano Colonna、Nicoleta Gaggero、Ezio Battistel、Daniele Bianchi

  DOI：10.1016/s0957-4166(00)86040-1

  日期：1992.8

  A systematic study of the stereochemistry of oxidation at sulfur catalyzed by cyclohexanone monooxygenase from Acinetobacter using as the substrates numerous alkyl aryl sulfides, dialkyl sulfides and dialkyl disulfides has been carried out. It was found that the structure of the sulfide dramatically influenced the enantioselectivity of the enzyme which yielded sulfoxides with optical purities ranging from 99% ee and R-configuration to 93% ee and S-configuration.
• 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).