[1R,2S,(S)S]-N-[1-(4-bromophenyl)-2-phenyl-2-(phenylselenyl)ethyl]-p-toluenesulfinamide | 1328883-77-7

• 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: [1R,2S,(S)S]-N-[1-(4-bromophenyl)-2-phenyl-2-(phenylselenyl)ethyl]-p-toluenesulfinamide
• 英文别名: (S)-N-[(1R,2S)-1-(4-bromophenyl)-2-phenyl-2-phenylselanylethyl]-4-methylbenzenesulfinamide
• CAS: 1328883-77-7
• 化学式: C₂₇H₂₄BrNOSSe
• 分子量: 569.424
• InChiKey: YYHZVPADIDFVSN-UFRMOSHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  48.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [1R,2S,(S)S]-N-[1-(4-bromophenyl)-2-phenyl-2-(phenylselenyl)ethyl]-p-toluenesulfinamide 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以68%的产率得到(1R,2S)-1-(4-bromophenyl)-2-phenyl-2-(phenylselenyl)ethanamine
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure anti-1,2-Diaryl and syn-1,2-Alkylaryl vic-Selenoamines

  摘要：

  Phenylselenyl benzylcarbanion stabilized by an (S)-2-p-tolylsulfinyl group evolves in a highly stereoselective way in the reactions with (S)-N-(p-tolylsulfinyl)imines at -98 degrees C affording diastereomerically pure 1,2-selenoamino derivatives in good yields. The syn or anti relationship of the obtained compounds depends on the alkyl or aryl character of the imine. They are easily transformed into enantiomerically pure (1R,2S)-1-aryl [or (1S,2S)-1-alkyl]-2-(phenylseleno)-2-phenylethylamines by reaction with t-BuLi and subsequent methanolysis of the generated sulfinamide derivatives with TFA.

  DOI：

  10.1021/jo202611v
• 作为产物：
  描述：

  (S)-1-methyl-2-(p-tolylsulfinyl)benzene 在 正丁基锂 、 叔丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 正戊烷 为溶剂， 反应 0.67h， 生成 [1R,2S,(S)S]-N-[1-(4-bromophenyl)-2-phenyl-2-(phenylselenyl)ethyl]-p-toluenesulfinamide
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure anti-1,2-Diaryl and syn-1,2-Alkylaryl vic-Selenoamines

  摘要：

  Phenylselenyl benzylcarbanion stabilized by an (S)-2-p-tolylsulfinyl group evolves in a highly stereoselective way in the reactions with (S)-N-(p-tolylsulfinyl)imines at -98 degrees C affording diastereomerically pure 1,2-selenoamino derivatives in good yields. The syn or anti relationship of the obtained compounds depends on the alkyl or aryl character of the imine. They are easily transformed into enantiomerically pure (1R,2S)-1-aryl [or (1S,2S)-1-alkyl]-2-(phenylseleno)-2-phenylethylamines by reaction with t-BuLi and subsequent methanolysis of the generated sulfinamide derivatives with TFA.

  DOI：

  10.1021/jo202611v

文献信息

• Synthesis of Enantiomerically Pure <i>anti</i>-1,2-Diaryl and <i>syn</i>-1,2-Alkylaryl <i>vic</i>-Selenoamines
  作者：José L. García Ruano、Esther Torrente、Inés Alonso、Mercedes Rodriguez、Ana M. Martín-Castro、Alessandro Degl’Innocenti、Lucrezia Frateschi、Antonella Capperucci

  DOI：10.1021/jo202611v

  日期：2012.2.17

  Phenylselenyl benzylcarbanion stabilized by an (S)-2-p-tolylsulfinyl group evolves in a highly stereoselective way in the reactions with (S)-N-(p-tolylsulfinyl)imines at -98 degrees C affording diastereomerically pure 1,2-selenoamino derivatives in good yields. The syn or anti relationship of the obtained compounds depends on the alkyl or aryl character of the imine. They are easily transformed into enantiomerically pure (1R,2S)-1-aryl [or (1S,2S)-1-alkyl]-2-(phenylseleno)-2-phenylethylamines by reaction with t-BuLi and subsequent methanolysis of the generated sulfinamide derivatives with TFA.