(S)-1-(2-naphthoyl)-3-[[1-(R)-phenylethyl]amino]pyrrolidine | 216669-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-(2-naphthoyl)-3-[[1-(R)-phenylethyl]amino]pyrrolidine
• 英文别名: naphthalen-2-yl-[(3S)-3-[[(1R)-1-phenylethyl]amino]pyrrolidin-1-yl]methanone
• CAS: 216669-31-7
• 化学式: C₂₃H₂₄N₂O
• 分子量: 344.456
• InChiKey: BWIGTVAOHAZDGZ-VGSWGCGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-naphthoyl)-3-[[1-(R)-phenylethyl]amino]pyrrolidine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以75%的产率得到(S)-1-(2-naphthylmethyl)-3-[[1-(R)-phenylethyl]amino]pyrrolidine
  参考文献：
  名称：

  Structure-Selectivity Relationship in Alkyllithium−Aldehyde Condensations Using 3-Aminopyrrolidine Lithium Amides as Chiral Auxiliaries

  摘要：

  A nonracemizing route to a set of chiral 3-aminopyrrolidines, based on 4-hydroxy-(L)-proline, is described. The induction potential of the lithium amides derived from these diamines has then been investigated in the asymmetric addition of alkyllithium compounds onto various aldehydes. Enantiomeric excesses up to 76% have been obtained in the case of the condensation of n-butyllithium onto o-tolualdehyde under standard experimental conditions (THF, -78 degrees C). Interestingly, the presence of a second asymmetric center, such as an alpha-methylbenzyl group, on the lateral 3-amino group gives access, according to its configuration, to one or the other of the 1-o-tolylpentan-1-ol enantiomers.

  DOI：

  10.1021/jo9810260
• 作为产物：
  描述：

  ((R)-3-Hydroxy-pyrrolidin-1-yl)-naphthalen-2-yl-methanone 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 68.0h， 生成 (S)-1-(2-naphthoyl)-3-[[1-(R)-phenylethyl]amino]pyrrolidine
  参考文献：
  名称：

  Structure-Selectivity Relationship in Alkyllithium−Aldehyde Condensations Using 3-Aminopyrrolidine Lithium Amides as Chiral Auxiliaries

  摘要：

  A nonracemizing route to a set of chiral 3-aminopyrrolidines, based on 4-hydroxy-(L)-proline, is described. The induction potential of the lithium amides derived from these diamines has then been investigated in the asymmetric addition of alkyllithium compounds onto various aldehydes. Enantiomeric excesses up to 76% have been obtained in the case of the condensation of n-butyllithium onto o-tolualdehyde under standard experimental conditions (THF, -78 degrees C). Interestingly, the presence of a second asymmetric center, such as an alpha-methylbenzyl group, on the lateral 3-amino group gives access, according to its configuration, to one or the other of the 1-o-tolylpentan-1-ol enantiomers.

  DOI：

  10.1021/jo9810260

文献信息

• Structure-Selectivity Relationship in Alkyllithium−Aldehyde Condensations Using 3-Aminopyrrolidine Lithium Amides as Chiral Auxiliaries
  作者：Aline Corruble、Jean-Yves Valnot、Jacques Maddaluno、Pierre Duhamel

  DOI：10.1021/jo9810260

  日期：1998.11.1

  A nonracemizing route to a set of chiral 3-aminopyrrolidines, based on 4-hydroxy-(L)-proline, is described. The induction potential of the lithium amides derived from these diamines has then been investigated in the asymmetric addition of alkyllithium compounds onto various aldehydes. Enantiomeric excesses up to 76% have been obtained in the case of the condensation of n-butyllithium onto o-tolualdehyde under standard experimental conditions (THF, -78 degrees C). Interestingly, the presence of a second asymmetric center, such as an alpha-methylbenzyl group, on the lateral 3-amino group gives access, according to its configuration, to one or the other of the 1-o-tolylpentan-1-ol enantiomers.