(R)-(+)-2-naphthyl-N-(pyridine-2-ylmethylene)ethanamine | 244018-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-(+)-2-naphthyl-N-(pyridine-2-ylmethylene)ethanamine
• 英文别名: N-[(1R)-1-naphthalen-2-ylethyl]-1-pyridin-2-ylmethanimine
• CAS: 244018-13-1
• 化学式: C₁₈H₁₆N₂
• 分子量: 260.338
• InChiKey: ZBUAGOXFBCUWHC-CQSZACIVSA-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 、 (R)-(+)-2-naphthyl-N-(pyridine-2-ylmethylene)ethanamine 以 乙腈 为溶剂， 生成 fac-Λ-[Fe((R)-(+)-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 、 (R)-(+)-1-(2-萘基)乙胺 以 甲苯 为溶剂， 反应 12.0h， 生成 (R)-(+)-2-naphthyl-N-(pyridine-2-ylmethylene)ethanamine
  参考文献：
  名称：

  Application of rapidly generated bidentate ligand libraries to zinc catalyzed reductions

  摘要：

  A methodology for the combinatorial synthesis of bidentate ligands - allowing direct screening of reaction products without the need for isolation or purification - has been employed in a zinc catalyzed hydrosilylation. This reaction allowed the robustness of the methodology to be examined, by employing it in a challenging case where the metal complex is not pre-formed prior to catalysis. Four different ligand families have been examined: imines, aminals, bis-imines and oxazolines and related compounds, with a small library of each type produced and directly screened in the reaction. Three ligands providing enantioselectivities of 50% or more in this very challenging reaction were identified, and ees and conversions were equivalent whether the ligand was obtained as a crude mixture from a library synthesis or as an isolated, purified compound. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.06.013

文献信息

• Rapid, in situ synthesis of bidentate ligands: chromatography-free generation of catalyst libraries
  作者：Robin Frauenlob、Martha M. McCormack、Carolyn M. Walsh、Enda Bergin

  DOI：10.1039/c1ob06180a

  日期：——

  The parallel synthesis of chiral bidentate ligands and their subsequent use in situ for a catalytic process is described. The ligands thus prepared gave comparable results to those obtained when the ligands were synthesized and purified by conventional means. This includes oxazolines and other compounds of similar complexity, meaning that for the first time these valuable compounds have been brought into the field of combinatorial catalysis.

  描述了手性双齿配体的并行合成及其随后在原位催化过程中使用。这样制备的配体所得到的结果与采用传统方法合成和纯化的配体相比具有可比性。这包括氧唑啉和其他具有类似复杂性的化合物，这意味着这些有价值的化合物首次被引入组合催化领域。
• Application of rapidly generated bidentate ligand libraries to zinc catalyzed reductions
  作者：Tariq Zaman、Robin Frauenlob、Robert McCarthy、Carolyn M. Walsh、Enda Bergin

  DOI：10.1016/j.jorganchem.2012.06.013

  日期：2012.10

  A methodology for the combinatorial synthesis of bidentate ligands - allowing direct screening of reaction products without the need for isolation or purification - has been employed in a zinc catalyzed hydrosilylation. This reaction allowed the robustness of the methodology to be examined, by employing it in a challenging case where the metal complex is not pre-formed prior to catalysis. Four different ligand families have been examined: imines, aminals, bis-imines and oxazolines and related compounds, with a small library of each type produced and directly screened in the reaction. Three ligands providing enantioselectivities of 50% or more in this very challenging reaction were identified, and ees and conversions were equivalent whether the ligand was obtained as a crude mixture from a library synthesis or as an isolated, purified compound. (C) 2012 Elsevier B.V. All rights reserved.
• 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.