N,N'-bis{[(S)-N-benzyl-pyrrolidin-2-yl]methyl}phenylenediamine | 384333-97-5

• 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: N,N'-bis{[(S)-N-benzyl-pyrrolidin-2-yl]methyl}phenylenediamine
• 英文别名: N,N'-bis([(S)-N-benzylpyrrolidin-2-yl]methyl)phenylenediamine；N,N'-bis[N-benzyl-2(S)-pyrrolidinylmethyl]phenylenediamine；1-N,2-N-bis[[(2S)-1-benzylpyrrolidin-2-yl]methyl]benzene-1,2-diamine
• CAS: 384333-97-5
• 化学式: C₃₀H₃₈N₄
• 分子量: 454.659
• InChiKey: LZPNIBNWPZYNSF-NSOVKSMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tetrakis(acetonitrile)copper(I) perchlorate 、 乙腈 、 N,N'-bis{[(S)-N-benzyl-pyrrolidin-2-yl]methyl}phenylenediamine 以 乙腈 为溶剂， 以80%的产率得到[Cu(N,N'-bis(N-benzyl-2(S)-2-pyrrolidinylmethyl)phenylenediamine)](ClO4)*MeCN
  参考文献：
  名称：

  Copper and manganese complexes with C2-multitopic ligands. X-ray crystal structure of [Cu(N,N′-bis[(S)-prolyl]phenylenediamine)H2O]. Catalytic properties

  摘要：

  Eight mononuclear complexes with multitopic C-2-symmetry ligands, [Cu(L)]ClO4, [Mn(L)Cl(H2O)]PF6, (L = N,N'-bis[(S)-prolyl]phenylenediamine (1), N,N'-bis[(S)-N-benzylprolyl]phenylenediamine (2), N,N'-bis{[(S)-pyrrolidin-2-yl]methyl}phenylenediamine (3), N,N'-bis-{[(S)-N-benzyl-pyrrolidin-2-yl]methyl}phenylenediamine (4)) have been prepared and characterised by analytical (elemental analysis, and mass spectroscopy) and FT IR, NMR and electronic spectroscopies. The data show that the ligands are neutral and coordinate to the metal in a tetradentate manner. The N,N'-bis[(S)-prolyl]phenylenediamine ligand also appears as an anionic species, (LH-2), and the single crystal structure determination of the respective complex, [Cu(1)]H2O, is reported. This new family of Cu-complexes catalyse the cyclopropanation of styrene with ethyl and t-butyl diazoacetate to afford cis/trans 2-phenylcyclopropan-1-carboxylates with good yields and selectivity against dimerisation and low ee ( < 10%). On the other hand, the manganese and copper complexes also catalyse the oxidation of organic sulfides to sulfoxides with high selectivity, and moderate to low en antioselectivity. If an excess of oxidant were used the reaction yields sulfone as only product with excellent yield. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0020-1693(02)00768-5
• 作为产物：
  描述：

  N,N'-bis[2(S)-2-pyrrolidinylmethyl]phenylenediamine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以87%的产率得到N,N'-bis{[(S)-N-benzyl-pyrrolidin-2-yl]methyl}phenylenediamine
  参考文献：
  名称：

  Synthesis of Rh(I) and Ir(I) complexes with chiral C2-multitopic ligands

  摘要：

  Four multitopic ligands, N,N'-bis[(S)-prolyl)phenylenediamine, N,N'-bis{[(S)-pyrrolidin-2-yl]methyl}phenylenediamine, N,N'-bis[(S)-N-benzylprolyl]phenylenediamine, N,N'-bis{[(S)-N-benzyl-pyrrolidin-2-yl]methyl}phenylenediamine, were synthesised and their co-ordination properties with Rh(I) and Ir(I) studied. The complexes were prepared by the reaction of [MC](cod)](2) with AgPF6 and further treatment with the ligand. All ligands form one to one [ML] species with the above metal ions. The structures of these complexes were elucidated by analytical and spectroscopic data (elemental analysis, mass spectroscopy, IR, H-1- and C-13-NMR). Complexes show excellent activities and enantioselectivities up to 30% for the hydrogenation of prochiral olefins under mild reaction conditions. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)01067-1

文献信息

• Synthesis of Rh(I) and Ir(I) complexes with chiral C2-multitopic ligands
  作者：M.J. Alcón、M. Iglesias、F. Sánchez、I. Viani

  DOI：10.1016/s0022-328x(01)01067-1

  日期：2001.9

  Four multitopic ligands, N,N'-bis[(S)-prolyl)phenylenediamine, N,N'-bis[(S)-pyrrolidin-2-yl]methyl}phenylenediamine, N,N'-bis[(S)-N-benzylprolyl]phenylenediamine, N,N'-bis[(S)-N-benzyl-pyrrolidin-2-yl]methyl}phenylenediamine, were synthesised and their co-ordination properties with Rh(I) and Ir(I) studied. The complexes were prepared by the reaction of [MC](cod)](2) with AgPF6 and further treatment with the ligand. All ligands form one to one [ML] species with the above metal ions. The structures of these complexes were elucidated by analytical and spectroscopic data (elemental analysis, mass spectroscopy, IR, H-1- and C-13-NMR). Complexes show excellent activities and enantioselectivities up to 30% for the hydrogenation of prochiral olefins under mild reaction conditions. (C) 2001 Elsevier Science B.V. All rights reserved.
• Copper and manganese complexes with C2-multitopic ligands. X-ray crystal structure of [Cu(N,N′-bis[(S)-prolyl]phenylenediamine)H2O]. Catalytic properties
  作者：M.J Alcón、Marta Iglesias、F Sánchez

  DOI：10.1016/s0020-1693(02)00768-5

  日期：2002.5

  Eight mononuclear complexes with multitopic C-2-symmetry ligands, [Cu(L)]ClO4, [Mn(L)Cl(H2O)]PF6, (L = N,N'-bis[(S)-prolyl]phenylenediamine (1), N,N'-bis[(S)-N-benzylprolyl]phenylenediamine (2), N,N'-bis[(S)-pyrrolidin-2-yl]methyl}phenylenediamine (3), N,N'-bis-[(S)-N-benzyl-pyrrolidin-2-yl]methyl}phenylenediamine (4)) have been prepared and characterised by analytical (elemental analysis, and mass spectroscopy) and FT IR, NMR and electronic spectroscopies. The data show that the ligands are neutral and coordinate to the metal in a tetradentate manner. The N,N'-bis[(S)-prolyl]phenylenediamine ligand also appears as an anionic species, (LH-2), and the single crystal structure determination of the respective complex, [Cu(1)]H2O, is reported. This new family of Cu-complexes catalyse the cyclopropanation of styrene with ethyl and t-butyl diazoacetate to afford cis/trans 2-phenylcyclopropan-1-carboxylates with good yields and selectivity against dimerisation and low ee ( < 10%). On the other hand, the manganese and copper complexes also catalyse the oxidation of organic sulfides to sulfoxides with high selectivity, and moderate to low en antioselectivity. If an excess of oxidant were used the reaction yields sulfone as only product with excellent yield. (C) 2002 Elsevier Science B.V. All rights reserved.