(S)-1-benzyl-3-(benzylamino)pyrrolidine | 145223-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-benzyl-3-(benzylamino)pyrrolidine
• 英文别名: 1-benzyl-3-benzylaminopyrrolidine；(S)-N,1-Dibenzylpyrrolidin-3-amine；(3S)-N,1-dibenzylpyrrolidin-3-amine
• CAS: 145223-69-4
• 化学式: C₁₈H₂₂N₂
• 分子量: 266.386
• InChiKey: BHEXKVGLZMEJRQ-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (R)-2-fluoro-2-phenylacetyl chloride 、 (S)-1-benzyl-3-(benzylamino)pyrrolidine 在 甲基锂 作用下， 生成
  参考文献：
  名称：

  Handy access to chiral N,N′-disubstituted 3-aminopyrrolidines.

  摘要：

  A new and rapid synthesis of (S)-3-aminopyrrolidines 7 is proposed from N-protected (S)-Asparagine. Basic cyclization of methyl N-Z-(S)-Asparaginate 1 followed by one-pot N-benzylation directly leads to (S)-aminosuccinimide 3 which, after cleavage of the Z-protecting group, is converted to corresponding imines and readily reduced to disubstituted chiral 3-aminopyrrolidines 7. Almost no racemization (less-than-or-equal-to 5%) of the original amino-acid asymmetric center may be observed.

  DOI：

  10.1016/s0957-4166(00)82081-9
• 作为产物：
  描述：

  (3S)-3-氨基-1-苄基吡咯烷-2,5-二酮 在 lithium aluminium tetrahydride 、 magnesium sulfate 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 (S)-1-benzyl-3-(benzylamino)pyrrolidine
  参考文献：
  名称：

  Handy access to chiral N,N′-disubstituted 3-aminopyrrolidines.

  摘要：

  A new and rapid synthesis of (S)-3-aminopyrrolidines 7 is proposed from N-protected (S)-Asparagine. Basic cyclization of methyl N-Z-(S)-Asparaginate 1 followed by one-pot N-benzylation directly leads to (S)-aminosuccinimide 3 which, after cleavage of the Z-protecting group, is converted to corresponding imines and readily reduced to disubstituted chiral 3-aminopyrrolidines 7. Almost no racemization (less-than-or-equal-to 5%) of the original amino-acid asymmetric center may be observed.

  DOI：

  10.1016/s0957-4166(00)82081-9

文献信息

• 3-Aminopyrrolidine lithium amide in enantioselective addition of organolithium compounds onto aromatic aldehydes
  作者：Aline Corruble、Jean-Yves Valnot、Jacques Maddaluno、Pierre Duhamel

  DOI：10.1016/s0957-4166(97)00114-6

  日期：1997.5

  New N,N′-disubstituted-3-aminopyrrolidines lithium amides have been used as chiral auxiliaries in the asymmetric condensation of n-butyllithium onto aromatic aldehydes, leading to e.e.s up to 73%.

  新的N，N'-二取代-3-氨基吡咯烷酮锂酰胺已被用作手性助剂，用于正丁基锂与芳香族醛的不对称缩合反应，可产生高达73％的ee。
• Handy access to chiral N,N′-disubstituted 3-aminopyrrolidines.
  作者：Jacques Maddaluno、Aline Corruble、Valéric Leroux、Gérard Plé、Pierre Duhamel

  DOI：10.1016/s0957-4166(00)82081-9

  日期：1992.10

  A new and rapid synthesis of (S)-3-aminopyrrolidines 7 is proposed from N-protected (S)-Asparagine. Basic cyclization of methyl N-Z-(S)-Asparaginate 1 followed by one-pot N-benzylation directly leads to (S)-aminosuccinimide 3 which, after cleavage of the Z-protecting group, is converted to corresponding imines and readily reduced to disubstituted chiral 3-aminopyrrolidines 7. Almost no racemization (less-than-or-equal-to 5%) of the original amino-acid asymmetric center may be observed.