N,N'-bis[(S)-N-benzylprolyl]ethylenediamine | 289480-96-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N'-bis[(S)-N-benzylprolyl]ethylenediamine
• 英文别名: (2S,2'S)-N,N'-(ethane-1,2-diyl)bis(1-benzylpyrrolidine-2-carboxamide)；(2S,2a(2)S)-N,Na(2)-1,2-Ethanediylbis[1-(phenylmethyl)-2-pyrrolidinecarboxamide]；(2S)-1-benzyl-N-[2-[[(2S)-1-benzylpyrrolidine-2-carbonyl]amino]ethyl]pyrrolidine-2-carboxamide
• CAS: 289480-96-2
• 化学式: C₂₆H₃₄N₄O₂
• 分子量: 434.582
• InChiKey: AMZJYDRXYBSGTG-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis[(S)-N-benzylprolyl]ethylenediamine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 N,N'-bis{[(S)-N-benzyl-pyrrolidin-2-yl]methyl}ethylenediamine
  参考文献：
  名称：

  一种新型三齿手性-NHC配体前体的合成与结构

  摘要：

  摘要 一种新型三齿手性咪唑鎓六氟磷酸酯是 N-杂环卡宾 (NHC) 配体的前体，由 (S)-脯氨酸分五步合成，总产率为 24%。通过NMR和元素分析表征该化合物。通过X射线衍射分析确定其分子结构。该手性化合物有两个立体中心，位于两个螯合侧链内，比旋光度为 -19.6°。

  DOI：

  10.1515/hc.2011.042
• 作为产物：
  描述：

  N-苄氧羰基-L-脯氨酸 在 palladium on activated charcoal 三乙胺 、 环己烯 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 N,N'-bis[(S)-N-benzylprolyl]ethylenediamine
  参考文献：
  名称：

  Rh and Ir complexes containing multidentate, C2-symmetry ligands. Structural and catalytic properties in asymmetric hydrogenation

  摘要：

  A comparative investigation of the interaction of Rh(I) and Ir(I) with a series of mixed-donor multidentate, C-2-symmetry ligands has been carried out. The complexes have been prepared by the reaction of [MCl(cod)](2) (cod = 1,5-cyclooctadiene) with AgPF6 and further treatment with the ligand. All ligands form 1:1 (metal:ligand) species with the above metal ions although, in a few instances, species of type [M2L2](2+) were also detected. The structures of these complexes were elucidated by analytical and spectroscopic data (elemental analysis, mass spectroscopy, IR, H-1- and C-13-NMR). Complexes were tested in the asymmetric hydrogenation of prochiral olefins, providing enantioselectivities up to 36%. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00083-8

文献信息

• Homogeneous and encapsulated within the cavities of zeolite Y chiral manganese and copper complexes with C2-multidentate ligands as catalysts for the selective oxidation of sulphides to sulfoxides or sulfones
  作者：M.J Alcón、A Corma、M Iglesias、F Sánchez

  DOI：10.1016/s1381-1169(01)00336-3

  日期：2002.1

  A series of manganese and copper complexes with tetradentate C-2-symmetry ligands, [Mn(C-2-ligand)Cl(H2O)]PF6 and [Cu(C-2-ligand)]ClO4, have been synthesised and characterised as homogeneous and encapsulated into the supercages of a large pore sized USY zeolite. These Mn and Cu complexes are excellent catalysts for the selective oxidation of organic sulphides to sulfoxides or sulfones with high selectivity, and moderate to low enantioselectivity. The chelation of zeolite-exchanged Mn2+ by C-N-containing ligands gives rise to a whole class of heterogeneous liquid phase oxidation, which exhibits similar catalytic performances than the homogeneous ones. Moreover, those heterogenised catalysts can be recycled in successive runs, by a simple filtration, without a significant loss of activity and selectivity. (C) 2002 Elsevier Science B.V. All rights reserved.
• Copper complexes with multidentate ligands derived from l-proline. X-ray crystal structure of {[Cu(N,N′-bis[(S)-prolyl]ethylenediamine)]ClO4}2·(MeCN)2
  作者：M.J Alcón、E Gutierrez-Puebla、M Iglesias、M.A Monge、F Sánchez

  DOI：10.1016/s0020-1693(00)00150-x

  日期：2000.8

  The reaction of [Cu(CH3CN)(4)]X (X = ClO4, PF6) with multidentate ligands N,N'-bis[(S)-prolyl]ethylenediamine (1), N,N'-bis[(S)-N-benzylprolyl]ethylenediamine (2), N,N'-bis [(S)-pyrrolidin-2-yl]methyl}ethylenediamine (3), N,N'-bis-[(S)-N-benzylpyrrolidin-2-yl]methyl}ethylenediamine (4) gives copper complexes which were characterised by analytical (elemental analysis, and mass spectroscopy) and FT IR, NMR and electronic spectroscopies. The [Cu(N,N'-bis[(S)-prolyl]ethylenediamine)]-ClO4}(2).(MeCN)(2) complex was characterised by X-ray crystallography. This new family of Cu-complexes catalyse the cyclopropanation of styrene with ethyl and t-butyl diazoacetate to yield cis/trans 2-phenylcyclopropan-1-carboxylates in good yields and selectivity against dimerisation and low ee (<10%). (C) 2000 Elsevier Science S.A. All rights reserved.
• Rh and Ir complexes containing multidentate, C2-symmetry ligands. Structural and catalytic properties in asymmetric hydrogenation
  作者：M.J Alcón、M Iglesias*、F Sánchez*、I Viani

  DOI：10.1016/s0022-328x(00)00083-8

  日期：2000.4

  A comparative investigation of the interaction of Rh(I) and Ir(I) with a series of mixed-donor multidentate, C-2-symmetry ligands has been carried out. The complexes have been prepared by the reaction of [MCl(cod)](2) (cod = 1,5-cyclooctadiene) with AgPF6 and further treatment with the ligand. All ligands form 1:1 (metal:ligand) species with the above metal ions although, in a few instances, species of type [M2L2](2+) were also detected. The structures of these complexes were elucidated by analytical and spectroscopic data (elemental analysis, mass spectroscopy, IR, H-1- and C-13-NMR). Complexes were tested in the asymmetric hydrogenation of prochiral olefins, providing enantioselectivities up to 36%. (C) 2000 Elsevier Science S.A. All rights reserved.
• Synthesis and structure of a novel tridentate chiral-NHC ligand precursor
  作者：Longguang Yang、Changsheng Cao、Rui Sun、Yu Peng、Lingzhi Zhang、Zhan Shi、Guangsheng Pang、Yanhui Shi

  DOI：10.1515/hc.2011.042

  日期：2011.12.1

  Abstract A novel tridentate chiral imidazolium hexafluorophosphate, a precursor for N-heterocyclic carbene (NHC) ligand, was synthesized from (S)-proline in five steps in 24% overall yield. The compound was characterized by NMR and elemental analysis. Its molecular structure was determined by X-ray diffraction analysis. This chiral compound has two stereogenic centers which are within two chelating

  摘要 一种新型三齿手性咪唑鎓六氟磷酸酯是 N-杂环卡宾 (NHC) 配体的前体，由 (S)-脯氨酸分五步合成，总产率为 24%。通过NMR和元素分析表征该化合物。通过X射线衍射分析确定其分子结构。该手性化合物有两个立体中心，位于两个螯合侧链内，比旋光度为 -19.6°。