(2S,3R)-N-(4-toluenesulfonyl)-2-(4-trifluoromethylphenyl)-3-(phenylthio)piperidine | 1613582-55-0

• 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: (2S,3R)-N-(4-toluenesulfonyl)-2-(4-trifluoromethylphenyl)-3-(phenylthio)piperidine
• 英文别名: 1-Tosyl-2beta-(4-(trifluoromethyl)phenyl)-3alpha-phenylthiopiperidine；(2S,3R)-1-(4-methylphenyl)sulfonyl-3-phenylsulfanyl-2-[4-(trifluoromethyl)phenyl]piperidine
• CAS: 1613582-55-0
• 化学式: C₂₅H₂₄F₃NO₂S₂
• 分子量: 491.598
• InChiKey: ZKASNOODPUUXCB-RPWUZVMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 甲烷磺酸 、 (S)-4-(diisopropylamino)-3,5-dimethyl-4,5-dihydro-3H-dinaphtho[2,1-d:1’,2’-f][1,3,2]diazaphosphepine-4-selenide 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 (2S,3R)-N-(4-toluenesulfonyl)-2-(4-trifluoromethylphenyl)-3-(phenylthio)piperidine 、 (2R,3S)-N-(4-toluenesulfonyl)-2-(4-trifluoromethylphenyl)-3-(phenylthio)piperidine
  参考文献：
  名称：

  Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins

  摘要：

  A method for the enantioselective, intramolecular sulfenoamination of various olefins has been developed using a chiral BINAM-based selenophosphoramide, Lewis base catalyst. Terminal and trans disubstituted alkenes afforded pyrrolidines, piperidines, and azepanes in high yields and high enantiomeric ratios via enantioselective formation and subsequent stereospecific capture of the thiiranium intermediate with the pendant tosyl-protected amine.

  DOI：

  10.1021/ja5046296

文献信息

• Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins
  作者：Scott E. Denmark、Hyung Min Chi

  DOI：10.1021/ja5046296

  日期：2014.6.25

  A method for the enantioselective, intramolecular sulfenoamination of various olefins has been developed using a chiral BINAM-based selenophosphoramide, Lewis base catalyst. Terminal and trans disubstituted alkenes afforded pyrrolidines, piperidines, and azepanes in high yields and high enantiomeric ratios via enantioselective formation and subsequent stereospecific capture of the thiiranium intermediate with the pendant tosyl-protected amine.