N²,N⁶-di(naphthalen-1-yl)pyridine-2,6-dicarboxamide | 132734-81-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N²,N⁶-di(naphthalen-1-yl)pyridine-2,6-dicarboxamide
• 英文别名: 2,6-bispyridine；N,N′-bis(1-naphthyl)pyridine-2,6-dicarboxamide；N,N'-bis(1-naphthyl)-2,6-pyridinedicarboximidate；N,N'-di(naphthalen-1-yl)pyridine-2,6-dicarboxamide；2-N,6-N-dinaphthalen-1-ylpyridine-2,6-dicarboxamide
• CAS: 132734-81-7
• 化学式: C₂₇H₁₉N₃O₂
• 分子量: 417.467
• InChiKey: OHTFBSAHBZXFJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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-di(naphthalen-1-yl)pyridine-2,6-dicarboxamide 以 氘代氯仿 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Chemical Mustard Containment Using Simple Palladium Pincer Complexes: The Influence of Molecular Walls

  摘要：

  Six amide-based NNN palladium(II) pincer complexes Pd(L)(CH3CN) were synthesized, characterized, and examined for binding the sulfur mustard surrogate, 2-chloroethyl ethyl sulfide (CEES). The complexes all bind readily with CEES as shown by 'H NMR spectroscopy in CDCl3. The influence of parasubstituents on the two amide phenyl appendages was explored as well as the effect of replacing the phenyl groups with larger aromatic rings, 1-naphthalene and 9-anthracene. While variations of the parasubstituents had only a slight influence on the binding affinities, incorporation of larger aromatic rings resulted in a significant size-related increase in binding, possibly due to increasing steric and electronic interactions. In crystal structures of three CEES-bound complexes, the mustard binds through the sulfur atom and lies along the aromatic walls of the side appendages approximately perpendicular to the pincer plane, with increasingly better alignment progressing from phenyl to 1-naphthalene to 9-anthracene.

  DOI：

  10.1021/ja408770u
• 作为产物：
  描述：

  吡啶-2,6-二甲酸 、 1-萘胺 在 吡啶 、 亚磷酸三苯酯 作用下， 反应 12.5h， 以88%的产率得到N²,N⁶-di(naphthalen-1-yl)pyridine-2,6-dicarboxamide
  参考文献：
  名称：

  Pd 2+离子的选择性荧光关闭感应：作为纸条，聚苯乙烯薄膜以及在细胞成像中的应用†

  摘要：

  带有附加萘基的吡啶-2,6-二甲酰胺基支架为荧光探针，用于选择性检测水性介质中的Pd 2+离子。包括Job曲线，Benesi-Hildebrand拟合，Stern-Volmer曲线和检测极限的集体研究表明，此类探针对Pd 2+离子具有显着的感测能力。这些探针进一步证明了作为纸条传感器，基于聚苯乙烯薄膜的传感器以及细胞成像的潜在应用。

  DOI：

  10.1039/c6ra27565f

文献信息

• Naphthyl- <i>vs</i>. anthrylpyridine-2,6-dicarboxamides in cation binding studies. Synthesis and spectroscopic properties
  作者：Natalia Łukasik、Ewa Wagner-Wysiecka、Véronique Hubscher-Bruder、Sylvia Michel、Maria Bocheńska、Beata Kamińska

  DOI：10.1080/10610278.2015.1119830

  日期：2016.8.2

  amines. For the obtained receptors, selective binding of lead(II) and copper(II) was found. Ion–receptor interactions were studied using UV–vis spectroscopy, spectrofluorimetry, 1H NMR and FTIR spectroscopy. The reversible lead(II) and copper(II) binding was discussed in regard of type of aromatic residue and amide bond localisation in aromatic ring, and binding model was proposed.

  摘要 以吡啶-2,6-甲酰二氯和相应的芳香胺为原料，采用简单的方法制备了带有α-或β-萘基-和α-或β-蒽基残基的吡啶-2,6-甲酰胺。对于获得的受体，发现了铅（II）和铜（II）的选择性结合。使用紫外-可见光谱、荧光光谱法、1H NMR 和 FTIR 光谱研究了离子-受体相互作用。从芳香残基的类型和芳香环中酰胺键的定位讨论了铅(II)和铜(II)的可逆结合，并提出了结合模型。
• 2,6-Bis[<i>N</i>-(8-quinolyl)carbamoyl]pyridine as a Highly Selective Extractant for Cu(II)
  作者：Kazuhisa Hiratani、Kazuhiro Taguchi

  DOI：10.1246/bcsj.63.3331

  日期：1990.11

  Pyridine derivatives containing two 8-quinolyl-amino groups were newly synthesized for heavy metal ion-cheletion. It was shown in solvent extraction that 2, 6-bis[N,N′-(8-quinolyl)aminocarbonyl]pyridine can extract only Cu(II) with excellent selectivity and efficiency from the aqueous phase(pH 6.2) containing Cu(II), Ni(II), Co(II), and Zn(II) into the chloroform phase.

  新合成了含有两个 8-喹啉氨基的吡啶衍生物用于重金属离子螯合。溶剂萃取表明，2, 6-双[N,N'-(8-喹啉基)氨基羰基]吡啶仅能以优异的选择性和效率从含有Cu(II)的水相(pH 6.2)中萃取Cu(II) )、Ni(II)、Co(II) 和 Zn(II) 进入氯仿相。
• Fast Carbon Dioxide Fixation by 2,6-Pyridinedicarboxamidato-nickel(II)-hydroxide Complexes: Influence of Changes in Reactive Site Environment on Reaction Rates
  作者：Deguang Huang、Olga V. Makhlynets、Lay Ling Tan、Sonny C. Lee、Elena V. Rybak-Akimova、R. H. Holm

  DOI：10.1021/ic200942u

  日期：2011.10.17

  bicarbonate product complexes [NiII(pyN2R2)(HCO3)]− having η1-OCO2H ligation. Fixation reactions follow second-order kinetics (rate = k2′[NiII–OH][CO2]) with negative activation entropies (−17 to −28 eu). Reactions were monitored by growth and decay of metal-to-ligand charge-transfer (MLCT) bands at 350–450 nm. The rate order R = Me > macro > Et > Pri > Bui > Ph at 298 K (macro = macrocylic pincer ligand)

  含有末端羟基的平面络合物[Ni II（pyN 2 R2）（OH）] -可以容易地由N，N '-（2,6-C 6 H 3 R 2）-2,6-吡啶二甲酰胺酸盐制备（2-）三齿钳状配体（R 4 N）（OH）和Ni（OTf）2。这些配合物在DMF中的溶液二氧化碳干净和完全反应在CO的过程2的固定与形成碳酸氢盐产物配合物[镍II（PYN 2 R2）（HCO 3）] -具有η 1 -OCO2 H结扎。固定反应遵循具有负激活熵（-17至-28 eu）的二级动力学（速率= k 2 '[Ni II -OH] [CO 2 ]）。通过在350–450 nm的金属至配体电荷转移（MLCT）谱带的生长和衰减来监控反应。298 K时的速率顺序R = Me>宏观> Et> Pr i > Bu i > Ph（宏观=大环钳形配体）反映了反应位点的空间位阻增加。这些复合物的固有的高反应性性质如下从ķ 2 '≈10 6中号-1小号-1对于R
• Ruthenium(II) complexes derived from the ligands having carboxamide groups: Reactivity and scavenging of nitric oxide (NO)
  作者：Kaushik Ghosh、Sushil Kumar、Rajan Kumar、Udai P. Singh

  DOI：10.1016/j.jorganchem.2013.10.054

  日期：2014.1

  Two novel ruthenium(II) complexes [Ru-II(L-1)(PPh3)(2)(CO)] (1) and [Ru-II(L-3)(PPh3)(2)(DMF)] (2) derived from the carboxamide ligands (LH2)-H-1 and (LH2)-H-2 respectively (where (LH2)-H-1 = N-2,N-6-dip-tolylpyridine-2,6-dicarboxamide and (LH2)-H-2 = N-2,N-6-di(naphthalen-1-yl)pyridine-2,6-dicarboxamide) were synthesized and characterized. Molecular structures of complexes 1 center dot CH3OH and 2 center dot DMF were authenticated using Xray crystallographic studies. Both the complexes were characterized using IR, UV-vis, elemental analysis, NMR and ESI-mass spectral studies. Electrochemical studies were performed to investigate the redox properties. Nitric oxide (NO) scavenging activity of these complexes was also observed with the help of Griess reagent reaction. (C) 2013 Elsevier B. V. All rights reserved.
• HIRATANI, KAZUHISA;TAGUCHI, KAZUHIRO, BULL. CHEM. SOC. JAP., 63,(1990) N1, C. 3331-3333
  作者：HIRATANI, KAZUHISA、TAGUCHI, KAZUHIRO

  DOI：——

  日期：——