ethyl (3S)-3-[[(1S)-1-phenylethyl]-prop-2-enylamino]butanoate | 487000-80-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (3S)-3-[[(1S)-1-phenylethyl]-prop-2-enylamino]butanoate
• CAS: 487000-80-6
• 化学式: C₁₇H₂₅NO₂
• 分子量: 275.391
• InChiKey: YQHVKLOIRQKHNP-GJZGRUSLSA-N

物化性质

• 沸点：
  345.3±30.0 °C(Predicted)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (3S)-3-[[(1S)-1-phenylethyl]-prop-2-enylamino]butanoate 在 4-二甲氨基吡啶 bis(η3-allyl-μ-chloropalladium(II)) 、 硫代水杨酸 、 N,N'-羰基二咪唑 、 1,4-双(二苯基膦)丁烷 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.0h， 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
• 作为产物：
  描述：

  反式-2-丁烯酸乙酯 、 lithium (S)-N-allyl-N-α-methylbenzyl amide 在 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到ethyl (3S)-3-[[(1S)-1-phenylethyl]-prop-2-enylamino]butanoate
  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.