tert-butyl (3S)-3-((R)-fluoro{2-[(S)-p-tolylsulfinyl]phenyl}methyl)-5-phenylpentanoate | 1363722-16-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: tert-butyl (3S)-3-((R)-fluoro{2-[(S)-p-tolylsulfinyl]phenyl}methyl)-5-phenylpentanoate
• 英文别名: tert-butyl (3S)-3-[(R)-fluoro-[2-[(S)-(4-methylphenyl)sulfinyl]phenyl]methyl]-5-phenylpentanoate
• CAS: 1363722-16-0
• 化学式: C₂₉H₃₃FO₃S
• 分子量: 480.644
• InChiKey: HNZWBTHMYCENHB-FQLJSUSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S)-3-((R)-fluoro{2-[(S)-p-tolylsulfinyl]phenyl}methyl)-5-phenylpentanoate 在 Raney Ni 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以80%的产率得到tert-butyl (3S)-3-[(R)-fluoro(phenyl)methyl]-5-phenylpentanoate
  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
• 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 0.08h， 生成 tert-butyl (3S)-3-((R)-fluoro{2-[(S)-p-tolylsulfinyl]phenyl}methyl)-5-phenylpentanoate
  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.