N²,N⁶-di-p-tolylpyridine-2,6-dicarboxamide | 126230-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N²,N⁶-di-p-tolylpyridine-2,6-dicarboxamide
• 英文别名: N²,N⁶-dip-tolylpyridine-2,6-dicarboxamide；2,6-(4-CH3C6H4NHCO)2C5H3N；N,N'-di-p-tolylpyridine-2,6-dicarboxamide；2-N,6-N-bis(4-methylphenyl)pyridine-2,6-dicarboxamide
• CAS: 126230-09-9
• 化学式: C₂₁H₁₉N₃O₂
• 分子量: 345.401
• InChiKey: ZKEYMAOJVMETCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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-p-tolylpyridine-2,6-dicarboxamide 在 氯化亚砜 、 sodium azide 、 五氯化磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  带有用于酮转移氢化的 2,6-双（四唑基）吡啶配体的钌（II）配合物催化剂

  摘要：

  摘要 合成了三种载有2,6-双(四唑基)吡啶的钌(II)配合物催化剂，对其进行了结构表征，并应用于酮的转移加氢。它们不同的催化活性归因于4-氯-2,6-双(1-(对甲苯基)-1H-四唑-5-基)吡啶钌(II)配合物上的不同膦配体，其中基于1,4-双(二苯基膦基)丁烷表现出更好的催化活性。各种酮被还原为相应的醇，转化率 >95%。

  DOI：

  10.1016/s1872-2067(17)62994-2
• 作为产物：
  描述：

  吡啶-2,6-二甲酸 、 乙烷,三氯氟- 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以61%的产率得到N²,N⁶-di-p-tolylpyridine-2,6-dicarboxamide
  参考文献：
  名称：

  Ruthenium(II) complexes derived from the ligands having carboxamide groups: Reactivity and scavenging of nitric oxide (NO)

  摘要：

  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.

  DOI：

  10.1016/j.jorganchem.2013.10.054

文献信息

• Facile Preparation of 6-Bromopyridine-2-carboxamide and Pyridine-2,6-dicarboxamide: Partial Aminocarbonylation of 2,6-Dibromopyridine
  作者：Hiroshi Horino、Hiroyuki Sakaba、Mannosuke Arai

  DOI：10.1055/s-1989-27372

  日期：——

  The palladium-catalyzed carbonylation of 2,6-dibromopyridine in the presence of primary amines under controlled conditions (carbon monoxide pressure) gives mainly N-aryl- or N-alkyl-6-bromopyridine-2-carboxamides accompanied by N,N′-diaryl- or N,N′-dialkylpyridine- 2,6-dicarboxamides. Further aminocarbonylation of the N-aryl- and N- alkyl-6-bromopyridine-2-carboxamides affords unsymmetric N,N′- diaryl, N-alkyl-N′-aryl-, or N,N′-dialkylpyridine-2,6-dicarboxamides.

  在受控条件下（如一氧化碳压力）下，钯催化的2,6-二溴吡啶与初级胺的羰基化反应主要生成N-芳基或N-烷基-6-溴吡啶-2-羧酰胺，并伴有N,N′-二芳基或N,N′-二烷基吡啶-2,6-二羧酰胺。对N-芳基和N-烷基-6-溴吡啶-2-羧酰胺进行进一步的氨基羰基化反应，可以得到不对称的N,N′-二芳基、N-烷基-N′-芳基或N,N′-二烷基吡啶-2,6-二羧酰胺。
• Dianilides of dipicolinic acid function as synthetic chloride channels
  作者：Carl R. Yamnitz、Saeedeh Negin、I. Alexandru Carasel、Rudolph K. Winter、George W. Gokel

  DOI：10.1039/b924812a

  日期：——

  We report that N2,N6-bis(4-nitrophenyl)pyridine-2,6-dicarboxamide, which is related to known isophthalic acid dianilides, transports Cl− ions through phospholipid bilayer membranes and shows clear evidence of channel activity.

  我们报告说，N2,N6-双（4-硝基苯基）吡啶-2,6-二甲酰胺与已知的间苯二甲酸二酰二胺相关，可通过磷脂双层膜转运 Cl- 离子，并显示出明确的通道活性证据。
• Chemical Mustard Containment Using Simple Palladium Pincer Complexes: The Influence of Molecular Walls
  作者：Qi-Qiang Wang、Rowshan Ara Begum、Victor W. Day、Kristin Bowman-James

  DOI：10.1021/ja408770u

  日期：2013.11.13

  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.
• N,N′-Bis(aryl)pyridine-2,6-dicarboxamide complexes of ruthenium: Synthesis, structure and redox properties
  作者：Moutusi Dasgupta、Sumon Nag、Gopal Das、Munirathinam Nethaji、Samaresh Bhattacharya

  DOI：10.1016/j.poly.2007.08.042

  日期：2008.1

  Reaction of five N,N'-bis(aryl)pyridine-2,6-dicarboxamides (H2L-R, where H-2 denotes the two acidic protons and R (R = OCH3, CH3, H, Cl and NO2) the para substituent in the aryl fragment) with [Ru(trpy)Cl-3](trpy = 2,2',2"-terpyridine) in refluxing ethanol in the presence of a base (NEW affords a group of complexes of the type [Ru-II(trpy)(L-R)], each of which contains an amide ligand coordinated to the metal center as a dianionic tridentate N,N,N-donor along with a terpyridine ligand. Structure of the [Ru-II(trpy)(L-Cl)] complex has been determined by X-ray crystallography. All the Ru(II) complexes are diamagnetic, and show characteristic H-1 NMR signals and intense MLCT transitions in the visible region. Cyclic voltammetry on the [Ru-II(trpy)(L-R)] complexes shows a Ru(II)-Ru(III) oxidation within 0.16-0.33 V versus SCE. An oxidation of the coordinated amide ligand is also observed within 0.94-1.33 V versus SCE and a reduction of coordinated terpyridine ligand within -1.10 to -1.15 V versus SCE. Constant potential coulometric oxidation of the [Ru-II(trpy)(L-R)] complexes produces the corresponding [Ru-II(trpy)(L-R)](+) complexes, which have been isolated as the perchlorate salts. Structure of the [Ru-III(trpy)(L-CH3)ClO4 complex has been determined by X-ray crystallography. All the Ru(Ill) complexes are one-electron paramagnetic, and show anisotropic ESR spectra at 77 K and intense LMCT transitions in the visible region. A weak ligand-field band has also been shown by all the [Ru-III(trpy)(L-R)]ClO4 complexes near 1600 nm. (C) 2007 Elsevier Ltd. All rights reserved.
• HORINO, HIROSHI;SAKABA, HIROYUKI;ARAI, MANNOSUKE, SYNTHESIS,(1989) N, C. 715-718
  作者：HORINO, HIROSHI、SAKABA, HIROYUKI、ARAI, MANNOSUKE

  DOI：——

  日期：——