N,N'-bis(3,5-bis(trifluoromethyl)phenyl)pyridine-2,6-dicarboxamide | 1287189-55-2

• 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: N,N'-bis(3,5-bis(trifluoromethyl)phenyl)pyridine-2,6-dicarboxamide
• 英文别名: N²,N⁶-bis(3,5-bis(trifluoromethyl)phenyl)pyridine-2,6-dicarboxamide；2-N,6-N-bis[3,5-bis(trifluoromethyl)phenyl]pyridine-2,6-dicarboxamide
• CAS: 1287189-55-2
• 化学式: C₂₃H₁₁F₁₂N₃O₂
• 分子量: 589.34
• InChiKey: SDTZPQJXZKTFKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  40
• 可旋转键数：
  4
• 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：
  15

反应信息

• 作为反应物：
  描述：

  N,N'-bis(3,5-bis(trifluoromethyl)phenyl)pyridine-2,6-dicarboxamide 在 hexafluorophosphoric acid 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 生成 2,6-bis(3,5-bis(trifluoromethyl)phenylcarbamoyl)pyridinium
  参考文献：
  名称：

  Syntheses of amide based anion receptors and investigation of their associations with anions and their molecular structures using proton NMR titration and DFT methods

  摘要：

  The synthesized disubstituted isophthalamide and pyridine-2,6dicarboxamide derivatives of nine compounds were prepared. Their association constants with tetrabutylammonium fluoride (TBA center dot F), tetrabutylammonium chloride (TBA center dot Cl), tetrabutylammonium bromide (TBA center dot Br), tetrabutylammonium dihydrogenphosphate (TBA center dot H2PO4), tetrabutylammonium hydrogensulphate (TBA center dot HSO4) and tetrabutylammonium nitrate (TBA center dot NO3) were obtained by H-1 NMR titration technique. The optimized structures of compounds 1-9 and their association with F-, Cl-, Br-, H2PO4-, HSO4- and NO3- were obtained using the B3LYP/6-31+G(d) method. The most favorable complex of compound 3 with Br- was found. The high association constants of complexes 1-6 with F- are expected. Associations of all receptors with anions are exothermic and spontaneous reactions. Thermodynamic properties of all associations obtained using B3LYP/6-31+G(d) method are reported. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.12.060
• 作为产物：
  描述：

  2,6-氯甲酰吡啶 、 间二(三氟甲基)苯胺 以 甲苯 为溶剂， 反应 12.0h， 以92%的产率得到N,N'-bis(3,5-bis(trifluoromethyl)phenyl)pyridine-2,6-dicarboxamide
  参考文献：
  名称：

  无需分离即可同时识别复杂混合物中的中性和阴离子物质

  摘要：

  据报道，化学感应系统无需分离技术即可运行，并且能够识别阴离子和结构相似的生物活性分子。在该策略中，分析物与具有开放结合裂缝的金属络合物的配位在 NMR 时间尺度上产生“静态结构”。通过策略性地将氟原子放置在靠近结合分析物的位置来产生独特的信号，这样微小的结构差异就会引起不同的19 F NMR 位移，从而可用于识别每种分析物。该方法的实用性通过量化咖啡中的咖啡因含量、通过识别茶和能量饮料中的成分以及通过区分距结合位点六个碳原子具有远程结构差异的多种生物胺来说明。我们进一步证明了复杂混合物中多种中性和阴离子物种的同时识别。

  DOI：

  10.1002/anie.201508085
• 作为试剂：
  描述：

  3-甲基喹啉 、 丙烯酸乙酯 在 palladium diacetate 、 N₂,N₆-Bis(2,6-dimethoxyphenyl)pyridine-2,6-dicarboxamide 、 N²-(2,6-dimethoxyphenyl)-N⁶-cis-(1-(pyridin-3-yl)-1,2,3,4-tetrahydronaphthalen-2-yl)pyridine-2,6-dicarboxamide 、 silver carbonate 、 六氟异丙醇 、 N-乙酰-DL-苯丙氨酸 、 4-二甲氨基吡啶 、 N,N'-bis(3,5-bis(trifluoromethyl)phenyl)pyridine-2,6-dicarboxamide 作用下， 以 二氯甲烷 、 1,4-二氧六环 、 叔丁醇 、 甲苯 为溶剂， 以64 %的产率得到ethyl (E)-3-(3-methylquinolin-7-yl)acrylate
  参考文献：
  名称：

  [EN] MOLECULAR EDITING OF MULTIPLE C-H BONDS BY LEVERAGING RECOGNITION OF DISTANCE, GEOMETRY AND CHIRALITY
  [FR] ÉDITION MOLÉCULAIRE DE LIAISONS C-H MULTIPLES PAR EXPLOITATION DE LA RECONNAISSANCE DE LA DISTANCE, DE LA GÉOMÉTRIE ET DE LA CHIRALITÉ

  摘要：

  This disclosure provides functional templates that direct Pd to functionalize multiple C-H bonds in polycyclic aza-arenes such as quinolines and related heterocycles at locations that are difficult to isolate and reach for substitution. Herein disclosed are two conceptually distinct directing templates (T) that enable site- selective C6 and C7-H activation of polycyclic aza-arenes. These catalytic pyridine-based templates recruit the aza-arene substrate throughN-coordination, enabling the directing arm to deliver the catalyst and precisely activate remote and adjacent C6 or C7-H bond (Fig. 1d). In parallel, we discovered that the use of a simple and readily prepared template chaperone (TC) can turn over the directing template, allowing it to be used catalytically for the first time. Notably, chiral recognition is vital in the granular discrimination between competing C3 and C7-H bonds when the differentiation via distance and geometry is insufficient. Thus, precise recognition of a directing template's distance, geometry and chirality now enables the iterative C-H editing of quinoline and related pharmacophores at any desired site and order. The methods disclosed herein can also be used for diverse and late-stage modification of heterocycle-based drug molecules and pharmacophores.

  公开号：

  WO2023212565A2

文献信息

• Synthesis and NMR Binding Studies towards Rational Design of a Series of Electron-Withdrawing Diamide Receptors/Organocatalysts
  作者：Michael Kinsella、Patrick G. Duggan、Jimmy Muldoon、Kevin S. Eccles、Simon E. Lawrence、Claire M. Lennon

  DOI：10.1002/ejoc.201001439

  日期：2011.2

  A related series of bisamides have been evaluated for rational correlation between anion complexation and organocatalysis: remarkable enhancement of hydrogen bonding to anions was observed along with significant increases in catalytic activity in the Baylis–Hillman reaction. In addition, X-ray crystallography showed a large degree of pre-organisation was observed in one receptor by incorporation of

  已经评估了一系列相关双酰胺的阴离子络合和有机催化之间的合理相关性：观察到氢键与阴离子的显着增强以及 Baylis-Hillman 反应中催化活性的显着增加。此外，X 射线晶体学表明，通过结合双（三氟甲基）苯胺基团和硫代酰胺官能团，在一个受体中观察到了很大程度的预组织。该系列中的新型双功能酰胺/N-酰基磺酰胺具有最佳催化性能。
• SENSOR AND METHOD OF DETECTING AN ANALYTE USING 19F NMR
  申请人：Massachusetts Institute of Technology

  公开号：US20160018344A1

  公开（公告）日：2016-01-21

  A sensor including a fluorinated receptor can be used to identify an analyte through shift in 19 F NMR resonance of the receptor when the receptor interacts with the analyte.
• Simultaneous Identification of Neutral and Anionic Species in Complex Mixtures without Separation
  作者：Yanchuan Zhao、Lily Chen、Timothy M. Swager

  DOI：10.1002/anie.201508085

  日期：2016.1.18

  A chemosensory system is reported that operates without the need for separation techniques and is capable of identifying anions and structurally similar bioactive molecules. In this strategy, the coordination of analytes to a metal complex with an open binding cleft generates “static structures” on the NMR timescale. Unique signals are created by strategically placing fluorine atoms in close proximity

  据报道，化学感应系统无需分离技术即可运行，并且能够识别阴离子和结构相似的生物活性分子。在该策略中，分析物与具有开放结合裂缝的金属络合物的配位在 NMR 时间尺度上产生“静态结构”。通过策略性地将氟原子放置在靠近结合分析物的位置来产生独特的信号，这样微小的结构差异就会引起不同的19 F NMR 位移，从而可用于识别每种分析物。该方法的实用性通过量化咖啡中的咖啡因含量、通过识别茶和能量饮料中的成分以及通过区分距结合位点六个碳原子具有远程结构差异的多种生物胺来说明。我们进一步证明了复杂混合物中多种中性和阴离子物种的同时识别。
• Syntheses of amide based anion receptors and investigation of their associations with anions and their molecular structures using proton NMR titration and DFT methods
  作者：Korakot Navakhun、Ranu Sawangsri、Vithaya Ruangpornvisuti

  DOI：10.1016/j.molstruc.2013.12.060

  日期：2014.3

  The synthesized disubstituted isophthalamide and pyridine-2,6dicarboxamide derivatives of nine compounds were prepared. Their association constants with tetrabutylammonium fluoride (TBA center dot F), tetrabutylammonium chloride (TBA center dot Cl), tetrabutylammonium bromide (TBA center dot Br), tetrabutylammonium dihydrogenphosphate (TBA center dot H2PO4), tetrabutylammonium hydrogensulphate (TBA center dot HSO4) and tetrabutylammonium nitrate (TBA center dot NO3) were obtained by H-1 NMR titration technique. The optimized structures of compounds 1-9 and their association with F-, Cl-, Br-, H2PO4-, HSO4- and NO3- were obtained using the B3LYP/6-31+G(d) method. The most favorable complex of compound 3 with Br- was found. The high association constants of complexes 1-6 with F- are expected. Associations of all receptors with anions are exothermic and spontaneous reactions. Thermodynamic properties of all associations obtained using B3LYP/6-31+G(d) method are reported. (C) 2013 Elsevier B.V. All rights reserved.