(R)-N-[(1S,2R)-1-(benzenesulfonyl)-1-fluoro-2-(4-methylphenyl)propan-2-yl]-2-methylpropane-2-sulfinamide | 1092458-11-1

• 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: (R)-N-[(1S,2R)-1-(benzenesulfonyl)-1-fluoro-2-(4-methylphenyl)propan-2-yl]-2-methylpropane-2-sulfinamide
• CAS: 1092458-11-1
• 化学式: C₂₀H₂₆FNO₃S₂
• 分子量: 411.562
• InChiKey: RNSMTVNBPUCWHO-QRRVGDGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  90.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  、 氟甲基苯基砜 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以218 mg的产率得到(R)-N-[(1R,2R)-1-(benzenesulfonyl)-1-fluoro-2-(4-methylphenyl)propan-2-yl]-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Stereoselective Monofluoromethylation of N-tert-Butylsulfinyl Ketimines Using Pregenerated Fluoro(phenylsulfonyl)methyl Anion

  摘要：

  Pregeneration of fluoro(phenylsulfonyl)methyl anion (PhSO2CHF-) paves the way for the efficient and highly stereoselective monofluoromethylation of (R)-N-tert-butylsulfinyl ketimines. The stereocontrol mode of the present diastereoselective monofluoromethylation of ketimines is different from the previously known nucleophilic fluoroalkylation of (R)-N-tert-butylsulfinyl aldimines, which suggests that a cyclic six-membered transition state (rather than a nonchelation controlled one) is involved in the current ketimine reaction.

  DOI：

  10.1021/ol802226k

文献信息

• Stereoselective Monofluoromethylation of <i>N-tert-</i>Butylsulfinyl Ketimines Using Pregenerated Fluoro(phenylsulfonyl)methyl Anion
  作者：Jun Liu、Laijun Zhang、Jinbo Hu

  DOI：10.1021/ol802226k

  日期：2008.12.4

  Pregeneration of fluoro(phenylsulfonyl)methyl anion (PhSO2CHF-) paves the way for the efficient and highly stereoselective monofluoromethylation of (R)-N-tert-butylsulfinyl ketimines. The stereocontrol mode of the present diastereoselective monofluoromethylation of ketimines is different from the previously known nucleophilic fluoroalkylation of (R)-N-tert-butylsulfinyl aldimines, which suggests that a cyclic six-membered transition state (rather than a nonchelation controlled one) is involved in the current ketimine reaction.