(2R,3R)-3-fluoro-3-{2-[(S)-p-tolylsulfinyl]phenyl}-2-(4-methoxyphenyl)prop-1-yl phenyl sulfone | 1363721-82-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2R,3R)-3-fluoro-3-{2-[(S)-p-tolylsulfinyl]phenyl}-2-(4-methoxyphenyl)prop-1-yl phenyl sulfone
• 英文别名: 1-[(1R,2R)-3-(benzenesulfonyl)-1-fluoro-2-(4-methoxyphenyl)propyl]-2-[(S)-(4-methylphenyl)sulfinyl]benzene
• CAS: 1363721-82-7
• 化学式: C₂₉H₂₇FO₄S₂
• 分子量: 522.661
• InChiKey: UKRCLIZUUAOARX-QOSYSIPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  88
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 正丁基锂 、 二异丙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 0.1h， 生成 (2R,3R)-3-fluoro-3-{2-[(S)-p-tolylsulfinyl]phenyl}-2-(4-methoxyphenyl)prop-1-yl phenyl sulfone 、 (2S,3R)-3-fluoro-3-{2-[(S)-p-tolylsulfinyl]phenyl}-2-(4-methoxyphenyl)prop-1-yl phenyl sulfone
  参考文献：
  名称：

  Stereocontrolled Fluorobenzylation of Vinyl Sulfones and α,β-Unsaturated Esters Mediated by a Remote Sulfinyl Group. Synthesis of Functionalized Enantiomerically Pure Benzylic Fluorides

  摘要：

  A sulfinyl group in an ortho position confers enough chemical and configurational stability to monofluorobenzylcarbanions to evolve in a completely stereoselective way in their reactions with beta-substituted vinyl sulfones and alpha,beta-unsaturated esters. Reactions afford easily separable mixtures of two epimers differing in the configuration of the center derived from the Michael acceptor (up to 98% de). They can be easily converted into enantiomerically pure gamma-fluorinated gamma-phenylsulfones and gamma-phenylesters bearing two chiral centers.

  DOI：

  10.1021/jo300174k

文献信息

• Stereocontrolled Fluorobenzylation of Vinyl Sulfones and α,β-Unsaturated Esters Mediated by a Remote Sulfinyl Group. Synthesis of Functionalized Enantiomerically Pure Benzylic Fluorides
  作者：José Luis García Ruano、José Antonio Fernández-Salas、M. Carmen Maestro

  DOI：10.1021/jo300174k

  日期：2012.3.16

  A sulfinyl group in an ortho position confers enough chemical and configurational stability to monofluorobenzylcarbanions to evolve in a completely stereoselective way in their reactions with beta-substituted vinyl sulfones and alpha,beta-unsaturated esters. Reactions afford easily separable mixtures of two epimers differing in the configuration of the center derived from the Michael acceptor (up to 98% de). They can be easily converted into enantiomerically pure gamma-fluorinated gamma-phenylsulfones and gamma-phenylesters bearing two chiral centers.