[1R,2S,(S)S]-N-{1-[(S)-(2-(p-toluenesulfinyl)phenyl)ethyl]pentyl}-p-toluenesulfinamide | 503819-55-4

• 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: [1R,2S,(S)S]-N-{1-[(S)-(2-(p-toluenesulfinyl)phenyl)ethyl]pentyl}-p-toluenesulfinamide
• 英文别名: (S)-4-methyl-N-[(2S,3R)-2-[2-[(S)-(4-methylphenyl)sulfinyl]phenyl]heptan-3-yl]benzenesulfinamide
• CAS: 503819-55-4
• 化学式: C₂₇H₃₃NO₂S₂
• 分子量: 467.697
• InChiKey: YOTKPNNYAITTSG-FSAUPZCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [1R,2S,(S)S]-N-{1-[(S)-(2-(p-toluenesulfinyl)phenyl)ethyl]pentyl}-p-toluenesulfinamide 在 镍 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (1R)-1-[(S)-1-(phenyl)ethyl]pentylamine N-(R)-MTPA amide
  参考文献：
  名称：

  Facile Synthesis of Optically Pure 1,2-Diaryl (and 1-Alkyl-2-aryl) Ethyl and Propylamines

  摘要：

  [GRAPHICS]A concise high-yielding route to synthetically useful 1,2-diaryl (and 1-alkyl-2-aryl) ethyl and propylamines in high enantiomeric purity is described. The key step of this route is the completely stereoselective addition of lithium (R)-ortho-(p-toluenesulfinyl)benzylic carbanions to (S)-N-p-toluenesulfinylimines, which takes place in very high or quantitative yields. N-Desulfinylation and C-desulfinylation of the resulting adducts can be achieved with no loss of optical. purity employing conventional methods (TFA and Raney-Ni, respectively).

  DOI：

  10.1021/ol027464h
• 作为产物：
  描述：

  (S)-(+)-对甲基苯亚磺酰胺 在 titanium(IV) tetraethanolate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 [1R,2S,(S)S]-N-{1-[(S)-(2-(p-toluenesulfinyl)phenyl)ethyl]pentyl}-p-toluenesulfinamide
  参考文献：
  名称：

  Facile Synthesis of Optically Pure 1,2-Diaryl (and 1-Alkyl-2-aryl) Ethyl and Propylamines

  摘要：

  [GRAPHICS]A concise high-yielding route to synthetically useful 1,2-diaryl (and 1-alkyl-2-aryl) ethyl and propylamines in high enantiomeric purity is described. The key step of this route is the completely stereoselective addition of lithium (R)-ortho-(p-toluenesulfinyl)benzylic carbanions to (S)-N-p-toluenesulfinylimines, which takes place in very high or quantitative yields. N-Desulfinylation and C-desulfinylation of the resulting adducts can be achieved with no loss of optical. purity employing conventional methods (TFA and Raney-Ni, respectively).

  DOI：

  10.1021/ol027464h

文献信息

• Facile Synthesis of Optically Pure 1,2-Diaryl (and 1-Alkyl-2-aryl) Ethyl and Propylamines
  作者：José L. García Ruano、José Alemán、José F. Soriano

  DOI：10.1021/ol027464h

  日期：2003.3.1

  [GRAPHICS]A concise high-yielding route to synthetically useful 1,2-diaryl (and 1-alkyl-2-aryl) ethyl and propylamines in high enantiomeric purity is described. The key step of this route is the completely stereoselective addition of lithium (R)-ortho-(p-toluenesulfinyl)benzylic carbanions to (S)-N-p-toluenesulfinylimines, which takes place in very high or quantitative yields. N-Desulfinylation and C-desulfinylation of the resulting adducts can be achieved with no loss of optical. purity employing conventional methods (TFA and Raney-Ni, respectively).