N,N'-双[[(2S)-吡咯烷-2-基]甲基]乙烷-1,2-二胺 | 56030-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: N,N'-双[[(2S)-吡咯烷-2-基]甲基]乙烷-1,2-二胺
• 英文名称: N,N'-bis([(S)-pirrolidin-2-yl]methyl)ethylenediamine
• 英文别名: N,N'-bis[[(S)-pyrrolidin-2-yl]methyl]ethylenediamine；N,N'-bis{[(S)-pyrrolidin-2-yl]methyl}ethylenediamine；N~1~,N~2~-Bis{[(2S)-pyrrolidin-2-yl]methyl}ethane-1,2-diamine；N,N'-bis[[(2S)-pyrrolidin-2-yl]methyl]ethane-1,2-diamine
• CAS: 56030-34-3
• 化学式: C₁₂H₂₆N₄
• 分子量: 226.365
• InChiKey: MFXQYAKSQCKTJA-RYUDHWBXSA-N

物化性质

• 沸点：
  333.0±10.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tetrakis(acetonitrile)copper(I) perchlorate 、 水 、 N,N'-双[[(2S)-吡咯烷-2-基]甲基]乙烷-1,2-二胺 以 not given 为溶剂， 以73%的产率得到[Cu(N,N'-bis([(S)-pyrrolidin-2-yl]methyl)ethylenediamine)]ClO4*2H2O
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0020-1693(00)00150-x
• 作为产物：
  描述：

  N,N'-Bis-(S-prolyl)-ethylendiamin 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以70%的产率得到N,N'-双[[(2S)-吡咯烷-2-基]甲基]乙烷-1,2-二胺
  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.
• 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.
• 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.