(S)-1-(2-naphthylmethyl)-3-[[1-(R)-phenylethyl]amino]pyrrolidine | 216669-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-(2-naphthylmethyl)-3-[[1-(R)-phenylethyl]amino]pyrrolidine
• 英文别名: (3S)-1-(naphthalen-2-ylmethyl)-N-[(1R)-1-phenylethyl]pyrrolidin-3-amine
• CAS: 216669-45-3
• 化学式: C₂₃H₂₆N₂
• 分子量: 330.473
• InChiKey: OKWWRRKGPVPGSE-JPYJTQIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-naphthylmethyl)-3-[[1-(R)-phenylethyl]amino]pyrrolidine 在 [6Li]-methyllithium 作用下， 以 氘代四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  烷基锂和手性锂酰胺之间聚集体的核磁共振和理论研究：通过单个不对称中心控制拓扑

  摘要：

  使用多核 ((1)H, (6)Li, (13)C, (15)N) 研究了甲基锂和手性 3-氨基吡咯烷 (3-AP) 氨基化锂之间的配合物，在其侧氨基上带有第二个不对称中心) 四氢呋喃-d(8) 中的低温核磁共振光谱。结果表明，锂螯合迫使 3-AP 的吡咯烷环采用类降冰片基构象，并且在介质中形成甲基锂和 3-AP 氨基锂之间的 1:1 非共价复合物。一组 (1)H-(1)H 和 (1)H-(6)Li 核磁共振交叉耦合相关性表明，甲基锂的结合可以沿着这种褶皱的“外”或“内”面发生结构，取决于横向手性基团的相对构型。这一聚集步骤使 3-氨基基团的氮呈手性，“ 即使考虑到溶剂，也几乎是等能的。这一结果表明混合聚集体的形成受到严格的动力学控制。提出了这些配合物的拓扑结构与烷基锂对芳香醛的对映选择性烷基化的诱导意义之间的关系。即使考虑到溶剂，也几乎是等能的。这一结果表明混合聚集体的形成受到严格的动力学

  DOI：

  10.1021/ja016945d
• 作为产物：
  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
• 作为试剂：
  描述：

  正丁基锂 、 2-甲基苯甲醛 在 (S)-1-(2-naphthylmethyl)-3-[[1-(R)-phenylethyl]amino]pyrrolidine 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R)-1-o-tolyl-1-pentanol 、 (-)-1-(2-methyl-phenyl)-pentan-1-ol
  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.
• A NMR and Theoretical Study of the Aggregates between Alkyllithium and Chiral Lithium Amides:  Control of the Topology through a Single Asymmetric Center
  作者：Aline Corruble、Daniel Davoust、Stéphanie Desjardins、Catherine Fressigné、Claude Giessner-Prettre、Anne Harrison-Marchand、Henri Houte、Marie-Claire Lasne、Jacques Maddaluno、Hassan Oulyadi、Jean-Yves Valnot

  DOI：10.1021/ja016945d

  日期：2002.12.1

  theory calculations show that the "exo" and "endo" arrangements are, for both diastereomers, almost isoenergetic even when solvent is taken into account. This result suggests that the formation of the mixed aggregates is under strict kinetic control. A relationship between the topology of these complexes and the sense of induction in the enantioselective alkylation of aromatic aldehydes by alkyllithiums

  使用多核 ((1)H, (6)Li, (13)C, (15)N) 研究了甲基锂和手性 3-氨基吡咯烷 (3-AP) 氨基化锂之间的配合物，在其侧氨基上带有第二个不对称中心) 四氢呋喃-d(8) 中的低温核磁共振光谱。结果表明，锂螯合迫使 3-AP 的吡咯烷环采用类降冰片基构象，并且在介质中形成甲基锂和 3-AP 氨基锂之间的 1:1 非共价复合物。一组 (1)H-(1)H 和 (1)H-(6)Li 核磁共振交叉耦合相关性表明，甲基锂的结合可以沿着这种褶皱的“外”或“内”面发生结构，取决于横向手性基团的相对构型。这一聚集步骤使 3-氨基基团的氮呈手性，“ 即使考虑到溶剂，也几乎是等能的。这一结果表明混合聚集体的形成受到严格的动力学控制。提出了这些配合物的拓扑结构与烷基锂对芳香醛的对映选择性烷基化的诱导意义之间的关系。即使考虑到溶剂，也几乎是等能的。这一结果表明混合聚集体的形成受到严格的动力学