(S)-1-phenylethyl((S)-pyrrolidin-2-ylmethyl)amine | 67715-15-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-1-phenylethyl((S)-pyrrolidin-2-ylmethyl)amine
• 英文别名: (1'S-phenylethyl)-(S)-pyrrolidin-2-ylmethylamine；S-1-phenyl-N-(S-pyrrolidin-2-ylmethyl)ethanamine；PPMA；(1S)-1-phenyl-N-[[(2S)-pyrrolidin-2-yl]methyl]ethanamine
• CAS: 67715-15-5
• 化学式: C₁₃H₂₀N₂
• 分子量: 204.315
• InChiKey: RKSJQMNRKQKFRA-AAEUAGOBSA-N

物化性质

• 沸点：
  302.6±15.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-phenylethyl((S)-pyrrolidin-2-ylmethyl)amine 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 13.0h， 生成 (5S)-2-[(S)-1-benzyl-2-hydroxyethylimino]-3-[(S)-1-phenylethyl]-1,3-diazabicyclo[3.3.0]octane
  参考文献：
  名称：

  Modified Guanidines as Potential Chiral Superbases. 1. Preparation of 1,3-Disubstituted 2-Iminoimidazolidines and the Related Guanidines through Chloroamidine Derivatives

  摘要：

  Modified guanidines were explored as potential chiral superbases. Thus, chiral 1,3-dimethyl-2-iminoimidazolidines with or without 4,5-diphenyl groups, their guanidinium salts, and the 2-iminoimidazolidines with (S)-1-phenylethyl groups on the ring nitrogens were prepared by treatment of 2-chloroimidazolinium chlorides with appropriate amines. Bicyclic guanidines were also prepared from a prolinamide using a similar procedure.

  DOI：

  10.1021/jo000744v
• 作为产物：
  描述：

  (S)-N-((S)-1-phenylethyl)pyrrolidine-2-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以86%的产率得到(S)-1-phenylethyl((S)-pyrrolidin-2-ylmethyl)amine
  参考文献：
  名称：

  衍生自l-脯氨酸的新型手性偶氮盐（N-杂环卡宾的前体）的合成与表征

  摘要：

  摘要 已经开发了用于制备衍生自1-脯氨酸的N-杂环卡宾的前体的七种手性氮杂鎓和五种官能化的手性氮杂鎓盐的短而灵活的方法。获得了中等至良好的总产量。分离出一些NHC二聚体和硫酮。还报道了两种[Rh-NHC]配合物的X射线晶体结构测定。 已经开发了用于制备衍生自1-脯氨酸的N-杂环卡宾的前体的七种手性氮杂鎓和五种官能化的手性氮杂鎓盐的短而灵活的方法。获得了中等至良好的总产量。分离出一些NHC二聚体和硫酮。还报道了两种[Rh-NHC]配合物的X射线晶体结构测定。

  DOI：

  10.1055/s-0033-1340215

文献信息

• Various P∗-chiral phosphite-type ligands: their synthesis, stereochemistry and use in Pd-catalysed allylation
  作者：Eduard B. Benetsky、Sergey V. Zheglov、Tatiana B. Grishina、Fliur Z. Macaev、Liudmila P. Bet、Vadim A. Davankov、Konstantin N. Gavrilov

  DOI：10.1016/j.tetlet.2007.09.125

  日期：2007.11

  available modular phosphite, phosphoramidite and diamidophosphite ligands with P∗-stereocentres have been prepared from inexpensive optically active precursors. Using these novel ligands, up to 91% ee was achieved in Pd-catalysed asymmetric allylic amination. The catalytic performance is affected greatly by the structure of the phosphocentre of the ligand.

  由廉价的光学活性前体制备了一个新的易于获得的，具有P ＊-立体中心的模块化亚磷酸酯，亚磷酰胺和亚酰胺基亚磷酸酯配体。使用这些新颖的配体，在Pd催化的不对称烯丙基胺化反应中可实现高达91％的ee。配体的磷中心的结构极大地影响了催化性能。
• Synthesis and characterization of chiral 1,2-diamines from 5-oxo-pyrrolidine-(S)-2-carboxylic acid
  作者：Uwe Köhn、Andrea Schramm、Florian Kloß、Helmar Görls、Evelyn Arnold、Ernst Anders

  DOI：10.1016/j.tetasy.2007.07.012

  日期：2007.7

  Unsymmetrical chiral secondary vicinal diamines were synthesized by applying a modified three-step reaction. The key step in this sequence is a primary amine mediated ring opening reaction of a diastereomeric oxazolidinone derivative. A possible mechanism for this step is described. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and X-ray crystal structure of dichloro[S-1-phenyl-N-(S-pyrrolidin-2-ylmethyl)ethanamine]zinc(II) and its catalytic application to rac-lactide polymerization
  作者：Saira Nayab、Hyosun Lee、Jong Hwa Jeong

  DOI：10.1016/j.poly.2010.11.002

  日期：2011.2

  New dichloro zinc(II) complex ligated by the homochiral bidentate ligand S-1-phenyl-N-(S-pyrrolidin-2-ylmethyl)ethanamine (PPMA) was synthesized and characterized by X-ray crystallography. The geometry of the (PPMA)ZnCl2 is a distorted tetrahedron comprising of zinc metal as a center linked with two N atoms of the PPMA in a bidentate coordination mode along with two chloro ligands. The catalytic capacity of the complex was evaluated in ring opening polymerization (ROP) of rac-lactide. The active catalyst species was generated in situ by treating MeLi to complex (PPMA)ZnCl2. The dimethyl derivative of the (PPMA)ZnCl2 showed highly activity in ROP of rac-lactide and gave preference to heterotactic polylactide. (C) 2010 Elsevier Ltd. All rights reserved.