N2,N6-bis-((R)-α-methylbenzyl)pyridine-2,6-dicarboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N2,N6-bis-((R)-α-methylbenzyl)pyridine-2,6-dicarboxamide
• 英文别名: N2,N6-bis((R)-α-methylbenzyl)pyridine-2,6-dicarboxamide；(R,R)-N,N'-bis(1-phenylethyl)-2,6-pyridinedicarboxamide；N,N'-bis((R)-1-phenylethyl)-2,6-pyridinedicarboxamide；N,N'-bis(1-phenylethyl)-2,6-pyridinedicarboxamide；2-N,6-N-bis[(1R)-1-phenylethyl]pyridine-2,6-dicarboxamide
• 化学式: C₂₃H₂₃N₃O₂
• 分子量: 373.455
• InChiKey: IOMBIMWBAOQSCB-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N2,N6-bis-((R)-α-methylbenzyl)pyridine-2,6-dicarboxamide 、 氯化钆 以 甲醇 为溶剂， 以66%的产率得到[Gd((R,R)-N,N'-bis(1-phenylethyl)-2,6-pyridinedicarboxamide)3]Cl3
  参考文献：
  名称：

  Structural and Photophysical Properties of Visible- and Near-IR-Emitting Tris Lanthanide(III) Complexes Formed with the Enantiomers of N,N′-Bis(1-phenylethyl)-2,6-pyridinedicarboxamide

  摘要：

  The enantiomers of N,N'-bis(1-phenylethyl)-2,6-pyridinedicarboxamide (L), namely, (R,R)-1, and (S,S)-1, react with Ln(III) ions to give stable [LnL(3)](3+) complexes in an anhydrous acetonitrile solution and in the solid state, as evidenced by electrospray ionization mass spectrometry, NMR, luminescence titrations, and their X-ray crystal structures, respectively. All [LnL(3)](3+) complexes [Ln(III) = Eu, Gd, Tb, and Yb; L = (R,R)-1 and (S,S)-1] are isostructural and crystallize in the cubic space group I23. Although the small quantum yields of the Ln(III)-centered luminescence clearly point to the poor efficiency of the luminescence sensitization by the ligand and the intersystem crossing and ligand-to-metal energy transfers, the ligand triplet-excited-state energy seems relatively well suited to sensitize many Ln(III) ion's emission for instance, in the visible (Eu and Tb), near-IR (Nd and Yb), or both regions (Pr, Sm, Dy, Er, and Tm).

  DOI：

  10.1021/ic202094p
• 作为产物：
  描述：

  2,6-氯甲酰吡啶 、 R(+)-alpha-甲基苄胺 生成 N2,N6-bis-((R)-α-methylbenzyl)pyridine-2,6-dicarboxamide
  参考文献：
  名称：

  发射检测到长寿命激发态的圆二色性：应用于手性Eu（III）系统。

  摘要：

  左旋和右旋圆偏振光激发后的外消旋齿状Eu（III）配合物与2,6-吡啶二羧酸加（+）-酒石酸二甲酯扰动的三价手性配合物的发光强度差异的测量提出了具有（R，R）-N，N′-双（1-苯乙基）-2，6-吡啶-二甲酰胺的Eu（III）。用于这些测量的实验技术在设计上与荧光检测的圆二色性光谱学相同，但由于Eu（III）激发态的寿命长，需要专门的仪器，因此在本手稿中称为发射检测的圆二色性（EDCD）。这些测量需要相对慢的入射圆偏振调制，这是用液晶偏振器完成的。

  DOI：

  10.1002/chir.20476

文献信息

• Optical isomers of N,N′-bis(1-phenylethyl)-2,6-pyridinedicarboxamide coordinated to europium(iii) ions as reliable circularly polarized luminescence calibration standards
  作者：Steven D. Bonsall、Mona Houcheime、Daniel A. Straus、Gilles Muller

  DOI：10.1039/b704346e

  日期：——

  The synthesis of two optical isomers of N,N′-bis(1-phenylethyl)-2,6-pyridinedicarboxamide and the constant circularly polarized luminescence (CPL) activity of their acetonitrile trivalent europium complex solutions over a long period of time open new perspectives for performing accurate routine CPL calibration tests at low cost.

  N,N-2-双(1-苯乙基)-2,6-吡啶二甲酰胺两种光学异构体的合成及其乙腈三价铕配合物溶液长期恒定的圆偏振发光(CPL)活性开启了新的研究领域以低成本执行准确的常规 CPL 校准测试的前景。
• A Promising Change in the Selection of the Circular Polarization Excitation Used in the Measurement of Eu(III) Circularly Polarized Luminescence
  作者：King Do、Françoise C. Muller、Gilles Muller

  DOI：10.1021/jp804463e

  日期：2008.7.1

  A judicious change in the selected transition used for circular polarization excitation will overcome the low oscillator strength limitation of the currently allowed magnetic-dipole (5)D1 <-- (7)F2 (Eu(III)) transition chosen for circularly polarized luminescence (CPL) measurement. The proposed allowed magnetic-dipole (5)D1 <-- (7)F0 (Eu(III)) transition will facilitate the detection of CPL from the

  用于圆偏振激发的选定跃迁的明智变化将克服当前允许的磁偶极子 (5)D1 <-- (7)F2 (Eu(III)) 跃迁的低振荡器强度限制，该跃迁选择用于圆偏振发光（ CPL) 测量。提议的允许磁偶极子 (5)D1 <-- (7)F0 (Eu(III)) 跃迁将有助于从感兴趣的 Eu(III) 系统检测 CPL。Eu(III) 与 (R,R)-N,N'-双(1-苯乙基)-2,6-吡啶二甲酰胺 ([Eu((R,R)-1 )3](3+))，最近建议作为一种有效和可靠的 CPL 校准剂，证实了所提出的实验程序的可行性。[Eu((R, R)-1)3](3+) 在 (5)D1 <-- (7)F0 跃迁的光谱范围内直接激发后和通过配体吸收带间接激发后 (λ(exc) = 308 nm)被观测到。这证实了推荐的磁偶极子允许吸收跃迁，(5)D1 <-- (7)F0，是在 CPL 测量中要考虑的跃迁。这项工作为持续的仪器改进提供了关键方向，可以将
• Emission detected circular dichroism from long-lived excited states: Application to chiral Eu(III) systems
  作者：Françoise C. Muller、Gilles Muller、James P. Riehl

  DOI：10.1002/chir.20476

  日期：2007.11

  right circularly polarized light for racemic terdentate Eu(III) complexes with 2,6-pyridine dicarboxylic acids perturbed by the addition of (+)-dimethyltartrate and for tris chiral complexes of Eu(III) with (R,R)-N,N'-bis(1-phenylethyl)-2,6-pyridine-dicarboxamide are presented. The experimental technique used for these measurements is identical in design to fluorescence detected circular dichroism spectroscopy

  左旋和右旋圆偏振光激发后的外消旋齿状Eu（III）配合物与2,6-吡啶二羧酸加（+）-酒石酸二甲酯扰动的三价手性配合物的发光强度差异的测量提出了具有（R，R）-N，N′-双（1-苯乙基）-2，6-吡啶-二甲酰胺的Eu（III）。用于这些测量的实验技术在设计上与荧光检测的圆二色性光谱学相同，但由于Eu（III）激发态的寿命长，需要专门的仪器，因此在本手稿中称为发射检测的圆二色性（EDCD）。这些测量需要相对慢的入射圆偏振调制，这是用液晶偏振器完成的。
• TTF salts of optically pure cobalt pyridine amidates; detection of soluble assemblies with stoichiometry corresponding to the solid state
  作者：Nikola Paul Chmel、Laura E. N. Allan、Jan M. Becker、Guy J. Clarkson、Scott S. Turner、Peter Scott

  DOI：10.1039/c0dt01184c

  日期：——

  interesting extended structures from 0D discrete units through 1D zigzag chains to 2D honeycomb layers. The complex anions were used in the synthesis of radical cation salts with tetrathiafulvalene (TTF). The salts (TTF)[CoIII(R,R-L1)2] and (TTF)[CoIII(S,S-L2)2]·EtOAc were characterised by single crystal X-ray diffraction and conductivity measurements. Both compounds comprise mono-oxidised TTF molecules and

  的光学纯阴离子配合物 吡啶甲酰胺配体，N 2，N 6-双（（R）-α-甲基苄基）吡啶-2，6-二甲酰胺H 2（R，R -L 1）和N 2，N 6-双（（S）-1-已经合成并充分表征了甲氧基丙烷-2-基）吡啶-2、6-二甲酰胺H 2（S，S -L 2）。配合物：（18-crown-6）K [Co III（R，R -L 1）2 ]，（18-crown-6）K [Fe III（R，R -L 1）2 ]和K [Co III（S，S -L 2）2 ]·3H 2 O显示出有趣的扩展结构，从0D离散单元到1D之字形链到2D蜂窝层。络合阴离子用于合成自由基阳离子盐，其中四硫富瓦烯（TTF）。通过单晶X射线衍射和电导率测量来表征盐（TTF）[Co III（R，R -L 1）2 ]和（TTF）[Co III（S，S -L 2）2 ]·EtOAc。两种化合物均包含单氧化的TTF分子，并显示相似的层状结构，没有直
• Structural and Photophysical Properties of Visible- and Near-IR-Emitting Tris Lanthanide(III) Complexes Formed with the Enantiomers of <i>N</i>,<i>N</i>′-Bis(1-phenylethyl)-2,6-pyridinedicarboxamide
  作者：KimNgan T. Hua、Jide Xu、Eliseo E. Quiroz、Sabrina Lopez、Andrew J. Ingram、Victoria Anne Johnson、Angela R. Tisch、Ana de Bettencourt-Dias、Daniel A. Straus、Gilles Muller

  DOI：10.1021/ic202094p

  日期：2012.1.2

  The enantiomers of N,N'-bis(1-phenylethyl)-2,6-pyridinedicarboxamide (L), namely, (R,R)-1, and (S,S)-1, react with Ln(III) ions to give stable [LnL(3)](3+) complexes in an anhydrous acetonitrile solution and in the solid state, as evidenced by electrospray ionization mass spectrometry, NMR, luminescence titrations, and their X-ray crystal structures, respectively. All [LnL(3)](3+) complexes [Ln(III) = Eu, Gd, Tb, and Yb; L = (R,R)-1 and (S,S)-1] are isostructural and crystallize in the cubic space group I23. Although the small quantum yields of the Ln(III)-centered luminescence clearly point to the poor efficiency of the luminescence sensitization by the ligand and the intersystem crossing and ligand-to-metal energy transfers, the ligand triplet-excited-state energy seems relatively well suited to sensitize many Ln(III) ion's emission for instance, in the visible (Eu and Tb), near-IR (Nd and Yb), or both regions (Pr, Sm, Dy, Er, and Tm).