(S)-(-)-1-naphthyl-N-(pyridine-2-ylmethylene)ethanamine | 115045-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-(-)-1-naphthyl-N-(pyridine-2-ylmethylene)ethanamine
• 英文别名: N-(2-pyridylmethylene)-(R)-1-naphtylethylamine；N-[(1S)-1-naphthalen-1-ylethyl]-1-pyridin-2-ylmethanimine
• CAS: 115045-82-4
• 化学式: C₁₈H₁₆N₂
• 分子量: 260.338
• InChiKey: KLHMIHIAILYVFI-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  iron(II) perchlorate hexahydrate 、 (S)-(-)-1-naphthyl-N-(pyridine-2-ylmethylene)ethanamine 以 乙腈 为溶剂， 生成 fac-Δ-[Fe((S)-(-)-1-naphthyl-N-(pyridine-2-ylmethylene)ethanamine)₃][ClO₄]₂·CH₃CN
  参考文献：
  名称：

  Synthesis, characterization, and DNA-binding of enantiomers of iron(II) Schiff base complexes

  摘要：

  Two pairs of iron(II) chiral enantiomers fac-Delta-[Fe(S-L1)(3)][ClO4](2) and fac-Lambda-[Fe(R-L1)(3)][ClO4](2) (Delta-1 and Lambda-1), fac-Delta-[Fe(S-L2)(3)][ClO4](2) and fac-Lambda-[Fe(R-L2)(3)][ClO4](2) (Delta-2 and Lambda-2), L1 = (R/S)-(+/-)-1-naphthyl-N-(pyridine-2-ylmethylene)ethanamine, L2 = (R/S)-(+/-)-2-naphthyl-N-(pyridine-2-ylmethylene)ethanamine were synthesized and characterized by elemental analysis, IR, UV-Vis, CD and H-1 NMR spectra. The X-ray structural analyses of Lambda-1 and Delta-2 revealed that the iron(II) complexes possess octahedral coordination geometry for N6 donor atoms by three bidentate ligands. R-L1 ligand induces the fac-Lambda isomer, while S-L2 ligand induces the fac-Delta isomer. The enantioselective binding of iron(II) chiral enantiomers to calf-thymus DNA (ct-DNA) has been investigated by methods of UV-Vis, fluorescence, and circular dichroism spectrometry. All the complexes could bind to ct-DNA and showed different binding affinities with the binding constants ranging from 0.91 x 10(5) to 1.43 x 10(5) M-1. Moreover, the Delta enantiomers exhibited more efficient DNA interaction with respect to the A enantiomers. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.12.027
• 作为产物：
  描述：

  吡啶-2-甲醛 、 (S)-(-)-1-(1-萘基)乙胺 以 乙腈 为溶剂， 反应 3.0h， 生成 (S)-(-)-1-naphthyl-N-(pyridine-2-ylmethylene)ethanamine
  参考文献：
  名称：

  Synthesis, characterization, and DNA-binding of enantiomers of iron(II) Schiff base complexes

  摘要：

  Two pairs of iron(II) chiral enantiomers fac-Delta-[Fe(S-L1)(3)][ClO4](2) and fac-Lambda-[Fe(R-L1)(3)][ClO4](2) (Delta-1 and Lambda-1), fac-Delta-[Fe(S-L2)(3)][ClO4](2) and fac-Lambda-[Fe(R-L2)(3)][ClO4](2) (Delta-2 and Lambda-2), L1 = (R/S)-(+/-)-1-naphthyl-N-(pyridine-2-ylmethylene)ethanamine, L2 = (R/S)-(+/-)-2-naphthyl-N-(pyridine-2-ylmethylene)ethanamine were synthesized and characterized by elemental analysis, IR, UV-Vis, CD and H-1 NMR spectra. The X-ray structural analyses of Lambda-1 and Delta-2 revealed that the iron(II) complexes possess octahedral coordination geometry for N6 donor atoms by three bidentate ligands. R-L1 ligand induces the fac-Lambda isomer, while S-L2 ligand induces the fac-Delta isomer. The enantioselective binding of iron(II) chiral enantiomers to calf-thymus DNA (ct-DNA) has been investigated by methods of UV-Vis, fluorescence, and circular dichroism spectrometry. All the complexes could bind to ct-DNA and showed different binding affinities with the binding constants ranging from 0.91 x 10(5) to 1.43 x 10(5) M-1. Moreover, the Delta enantiomers exhibited more efficient DNA interaction with respect to the A enantiomers. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.12.027

文献信息

• Synthesis, Characterization, Properties, and Asymmetric Catalytic Diels−Alder Reactions of Chiral-at-Metal Imino−Iridium(III) Complexes
  作者：Daniel Carmona、Fernando J. Lahoz、Sergio Elipe、Luis A. Oro、M. Pilar Lamata、Fernando Viguri、Carlos Mir、Carlos Cativiela、M. Pilar López-Ram de Víu

  DOI：10.1021/om980112n

  日期：1998.7.1

  and (SIr,RC)-[(η5-C5Me5)IrCl(imine)][SbF6] (imine = Ln = N-(2-pyridylmethylene)−(R)-1-phenylethylamine (L1; 1a,a‘), N-(2-pyridylmethylene)-(R)-1-naphthylethylamine (L2; 2a,a‘), N-(2-quinolylmethylene)−(R)-1-naphthylethylamine (L3; 3a,a‘), N-(6-methyl-2-pyridylmethylene)−(R)-1-naphthylethylamine (L4; 4a,a‘), N-(2-pyridylmethylene)−(R)-1-cyclohexylethylamine (L5; 5a,a‘), N-(2-pyridylmethylene)−(1R,2S,4R)-1-bornylamine)

  的合成和光学活性亚氨基配合物（表征ř铱，[R Ç） -和（小号的Ir，- [R Ç） - [（η 5 -C 5我5）的IrCl（亚胺）] [的SbF 6 ]（亚胺= L Ñ = N-（2-吡啶基亚甲基）-（R）-1-苯基乙胺（L 1 ; 1a，a '），N-（2-吡啶基亚甲基）-（R）-1-萘乙胺（L 2 ; 2a，a '） ，N-（2-喹啉基亚甲基）-（R）-1-萘乙胺（L 3 ; 3a，a '），N-（6-甲基-2-吡啶基亚甲基）-（R）-1-萘乙胺（L 4 ; 4a，a '），N-（2-吡啶基亚甲基）-（R）-1-环己基乙胺（L 5 ; 5a，a '），N-（2-吡啶基亚甲基）-（1 R， 2 S， 4 R）-1-冰片胺）（L 6 ; 6a，a '）），（R Ir，R C）-和（S Ir，ř Ç） - [（η 5 -C 5我5）的IrCl（L 2）] [A]（其中A = Cl（图7A中，'），BF
• Synthesis, characterization, and DNA-binding of enantiomers of iron(II) Schiff base complexes
  作者：Zhi-Guo Gu、Jing-Jing Na、Fei-Fei Bao、Xin-Xin Xu、Wen Zhou、Chun-Yan Pang、Zaijun Li

  DOI：10.1016/j.poly.2012.12.027

  日期：2013.3

  Two pairs of iron(II) chiral enantiomers fac-Delta-[Fe(S-L1)(3)][ClO4](2) and fac-Lambda-[Fe(R-L1)(3)][ClO4](2) (Delta-1 and Lambda-1), fac-Delta-[Fe(S-L2)(3)][ClO4](2) and fac-Lambda-[Fe(R-L2)(3)][ClO4](2) (Delta-2 and Lambda-2), L1 = (R/S)-(+/-)-1-naphthyl-N-(pyridine-2-ylmethylene)ethanamine, L2 = (R/S)-(+/-)-2-naphthyl-N-(pyridine-2-ylmethylene)ethanamine were synthesized and characterized by elemental analysis, IR, UV-Vis, CD and H-1 NMR spectra. The X-ray structural analyses of Lambda-1 and Delta-2 revealed that the iron(II) complexes possess octahedral coordination geometry for N6 donor atoms by three bidentate ligands. R-L1 ligand induces the fac-Lambda isomer, while S-L2 ligand induces the fac-Delta isomer. The enantioselective binding of iron(II) chiral enantiomers to calf-thymus DNA (ct-DNA) has been investigated by methods of UV-Vis, fluorescence, and circular dichroism spectrometry. All the complexes could bind to ct-DNA and showed different binding affinities with the binding constants ranging from 0.91 x 10(5) to 1.43 x 10(5) M-1. Moreover, the Delta enantiomers exhibited more efficient DNA interaction with respect to the A enantiomers. (C) 2013 Elsevier Ltd. All rights reserved.