(3S,4R,5S,1'S) ethyl-2,2,5-trimethyl-1-(1'-phenylethyl)-3-phenylsulfanyl-pyrrolidin-4-carboxylate | 487000-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3S,4R,5S,1'S) ethyl-2,2,5-trimethyl-1-(1'-phenylethyl)-3-phenylsulfanyl-pyrrolidin-4-carboxylate
• 英文别名: ethyl (2S,3R,4S)-2,5,5-trimethyl-1-[(1S)-1-phenylethyl]-4-phenylsulfanylpyrrolidine-3-carboxylate
• CAS: 487000-87-3
• 化学式: C₂₄H₃₁NO₂S
• 分子量: 397.582
• InChiKey: YBNPBZDSHYEVNL-GPHNJDIKSA-N

物化性质

• 沸点：
  474.7±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S,1'S) ethyl-2,2,5-trimethyl-1-(1'-phenylethyl)-3-phenylsulfanyl-pyrrolidin-4-carboxylate 、 3,5-二硝基苯甲酰氯 在 palladium dihydroxide 作用下， 生成
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure 2,2,3,4,5-Pentasubstituted Pyrrolidines by Phenylsulfanyl Migration

  摘要：

  [GRAPHICS]Enantiomerically pure 2,2,3,4,5-pentasubstituted pyrrolidines can be prepared, in high overall yield, from alpha-,beta-unsaturated esters. Asymmetry is introduced via a Michael addition, and additional stereogenic centers are introduced by an aldol reaction. A novel stereospecific ring-forming reaction, proceeding via a thiiranlum (episulfonium) ion, yields pyrrolidines from beta-hydroxy sulfides. In this manner, 2,2,3,4,5-pentasubstituted pyrrolidines, containing three contiguous stereogenic centers around the ring, can be prepared in 44% overall yield from ethyl crotonate.

  DOI：

  10.1021/ol0268384
• 作为产物：
  描述：

  反式-2-丁烯酸乙酯 在 4-二甲氨基吡啶 正丁基锂 、 ammonium cerium(IV) nitrate 、 水 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.5h， 生成 (3S,4R,5S,1'S) ethyl-2,2,5-trimethyl-1-(1'-phenylethyl)-3-phenylsulfanyl-pyrrolidin-4-carboxylate
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure 2,2,3,4,5-Pentasubstituted Pyrrolidines by Phenylsulfanyl Migration

  摘要：

  [GRAPHICS]Enantiomerically pure 2,2,3,4,5-pentasubstituted pyrrolidines can be prepared, in high overall yield, from alpha-,beta-unsaturated esters. Asymmetry is introduced via a Michael addition, and additional stereogenic centers are introduced by an aldol reaction. A novel stereospecific ring-forming reaction, proceeding via a thiiranlum (episulfonium) ion, yields pyrrolidines from beta-hydroxy sulfides. In this manner, 2,2,3,4,5-pentasubstituted pyrrolidines, containing three contiguous stereogenic centers around the ring, can be prepared in 44% overall yield from ethyl crotonate.

  DOI：

  10.1021/ol0268384

文献信息

• Synthesis of Enantiomerically Pure 2,2,3,4,5-Pentasubstituted Pyrrolidines by Phenylsulfanyl Migration
  作者：I. Craig Baldwin、Paul Briner、Martin D. Eastgate、David J. Fox、Stuart Warren

  DOI：10.1021/ol0268384

  日期：2002.12.1

  [GRAPHICS]Enantiomerically pure 2,2,3,4,5-pentasubstituted pyrrolidines can be prepared, in high overall yield, from alpha-,beta-unsaturated esters. Asymmetry is introduced via a Michael addition, and additional stereogenic centers are introduced by an aldol reaction. A novel stereospecific ring-forming reaction, proceeding via a thiiranlum (episulfonium) ion, yields pyrrolidines from beta-hydroxy sulfides. In this manner, 2,2,3,4,5-pentasubstituted pyrrolidines, containing three contiguous stereogenic centers around the ring, can be prepared in 44% overall yield from ethyl crotonate.