(S)-(-)-2-naphthyl-N-(pyridine-2-ylmethylene)ethanamine | 244018-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-(-)-2-naphthyl-N-(pyridine-2-ylmethylene)ethanamine
• 英文别名: N-[(1S)-1-naphthalen-2-ylethyl]-1-pyridin-2-ylmethanimine
• CAS: 244018-14-2
• 化学式: C₁₈H₁₆N₂
• 分子量: 260.338
• InChiKey: ZBUAGOXFBCUWHC-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)-(-)-2-naphthyl-N-(pyridine-2-ylmethylene)ethanamine 以 乙腈 为溶剂， 生成 fac-Δ-[Fe((S)-(-)-2-naphthyl-N-(pyridine-2-ylmethylene)ethanamine)₃][ClO₄]₂·2CH₃CN
  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-(2-萘基)乙胺 以 乙腈 为溶剂， 反应 3.0h， 生成 (S)-(-)-2-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