(+)-N-<2-(2(R)-Phenyl-1-(phenylthio)ethyl)>-5(S)-phenyl-2-pyrrolidine | 132959-49-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (+)-N-<2-(2(R)-Phenyl-1-(phenylthio)ethyl)>-5(S)-phenyl-2-pyrrolidine
• 英文别名: (+)-N-{2-[2(R)-Phenyl-1-(phenylthio)ethyl]}-5(S)-phenyl-2-pyrrolidine；(2S)-2-phenyl-1-[(1R)-1-phenyl-2-phenylsulfanylethyl]pyrrolidine
• CAS: 132959-49-0
• 化学式: C₂₄H₂₅NS
• 分子量: 359.535
• InChiKey: FTXMWAAVJUTSIO-ZEQRLZLVSA-N

物化性质

• 沸点：
  494.7±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+)-N-<2-(2(R)-Phenyl-1-(phenylthio)ethyl)>-5(S)-phenyl-2-pyrrolidine 在 lithium di-tert-butylbiphenylide 作用下， 以 四氢呋喃 为溶剂， 以51%的产率得到(S)-2-苯基吡咯烷
  参考文献：
  名称：

  A simple asymmetric synthesis of 2-substituted pyrrolidines and 5-substituted pyrrolidinones

  摘要：

  An efficient procedure for the preparation of the title compounds in high enantiomeric purity has been realized starting from 3-acylpropionic acids. Stereoselective reduction of chiral bicyclic lactams 2a-h, prepared from the corresponding gamma-keto acid and (R)-phenylglycinol, using alane or triethylsilane with titanium tetrachloride provided the N-substituted pyrrolidines and pyrrolidinones, respectively. Subsequent cleavage of the phenylglycinol returned the desired amines and lactams. The enantiomeric purity of these compounds was determined to be > 98% by chiral stationary-phase HPLC.

  DOI：

  10.1021/jo00032a012
• 作为产物：
  描述：

  (3R-顺)-3,7A-二苯基L四氢吡咯并-[2,1-B]唑-5(6H)-酮 在 lithium aluminium tetrahydride 、 三氯化铝 、 三乙基膦 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 15.33h， 生成 (+)-N-<2-(2(R)-Phenyl-1-(phenylthio)ethyl)>-5(S)-phenyl-2-pyrrolidine
  参考文献：
  名称：

  A simple asymmetric synthesis of 2-substituted pyrrolidines and 5-substituted pyrrolidinones

  摘要：

  An efficient procedure for the preparation of the title compounds in high enantiomeric purity has been realized starting from 3-acylpropionic acids. Stereoselective reduction of chiral bicyclic lactams 2a-h, prepared from the corresponding gamma-keto acid and (R)-phenylglycinol, using alane or triethylsilane with titanium tetrachloride provided the N-substituted pyrrolidines and pyrrolidinones, respectively. Subsequent cleavage of the phenylglycinol returned the desired amines and lactams. The enantiomeric purity of these compounds was determined to be > 98% by chiral stationary-phase HPLC.

  DOI：

  10.1021/jo00032a012

文献信息

• A simple asymmetric synthesis of 2-substituted pyrrolidines from 3-acylpropionic acids
  作者：A. I. Meyers、Laurence E. Burgess

  DOI：10.1021/jo00007a011

  日期：1991.3

  The title compounds have been prepared from 3-acylpropionic acids 2 and (-)-R-phenylglycinol in a three-step sequence in > 98% enantiomeric excess. The R group in 2 ultimately becomes the 2-substituent in the chiral pyrrolidine.
• MEYERS, A. I.;BURGESS, LAURENCE E., J. ORG. CHEM., 56,(1991) N, C. 2294-2296
  作者：MEYERS, A. I.、BURGESS, LAURENCE E.

  DOI：——

  日期：——