N-(pyridin-2-yl)isonicotinamide | 59898-94-1

• 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: N-(pyridin-2-yl)isonicotinamide
• 英文别名: N-(2-pyridyl)isonicotinamide；N-2-Pyridilisonicotinamid；N-pyridin-2-ylpyridine-4-carboxamide
• CAS: 59898-94-1
• 化学式: C₁₁H₉N₃O
• mdl: MFCD00455921
• 分子量: 199.212
• InChiKey: AVRWFGNRKDLVDQ-UHFFFAOYSA-N

物化性质

• 熔点：
  133-136°C
• 沸点：
  286.1±15.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  壬二酸 、 N-(pyridin-2-yl)isonicotinamide 以 乙酸乙酯 为溶剂， 反应 1080.0h， 生成 SVP-4n-AzA (3-pyridyl)-CONH-(2-pyridyl), HOOC-(CH2)7-COOH
  参考文献：
  名称：

  Establishing Supramolecular Control over Solid-State Architectures: A Simple Mix and Match Strategy

  摘要：

  With the help of robust principles of crystal engineering, it is possible to construct co-crystals where two or more different molecular entities coexist in the same crystalline lattice; the supramolecular assembly is driven by noncovalent interactions, most commonly by hydrogen bonds. We have synthesized two ditopic amide based ligands (N-(4-pyridin-2-yl)-isonicotinamide) and (N-(3-pyridin-2-yl)nicotinamide) and systematically established their binding preferences when faced with aliphatic dicarboxylic acids with an odd and even number of carbon atoms. Each ligand was co-crystallized with four odd and four even-chain dicarboxylic acids, and 13/16 reactions produced crystals suitable for single-crystal structure determination. On the basis of these results, it is dear that carefully selected systems can be manipulated to produce assemblies in the solid state with very precise control over topology and dimensionality. These ligands can be made to produce either 0-D or 1-D architectures simply by fine-tuning the choice of co-crystallizing agent in the supramolecular synthesis. This mix-and-match strategy allows us to mimic the reliability and versatility of covalent synthesis, in terms of successfully preparing a target with predetermined connectivity and metrics.

  DOI：

  10.1021/cg300180b
• 作为产物：
  描述：

  methyl 4-(pyridin-2-ylcarbamoyl)benzoate 在 吡啶 、 盐酸 、 十二羰基三钌 、 异丙醇 、 三氯氧磷 作用下， 以 DCM 、 水 为溶剂， 反应 40.5h， 生成 N-(pyridin-2-yl)isonicotinamide
  参考文献：
  名称：

  钌催化的N-（2-吡啶基）酰胺与异丙醇和芳基硼酸酯的还原化

  摘要：

  描述了一种新的酰胺与稳定反应物的三组分还原芳基化反应（iPrOH和芳基硼酸酯），利用2-吡啶基（Py）导向基团。N-Py-酰胺底物可以很容易地由羧酸和PyNH 2制备，所得的N-Py-1-芳基烷胺反应产物很容易通过用HCl取代HN-Py基团而转化为相应的氯化物。1-芳基-1-氯代烷烃产品可进行取代和交叉偶联反应。因此，获得了将羧酸转化成各种官能团的通用方案。Py‐NH 2副产物可以回收利用。

  DOI：

  10.1002/anie.201810947

文献信息

• A Cross-Coupling Approach to Amide Bond Formation from Esters
  作者：Taoufik Ben Halima、Jaya Kishore Vandavasi、Mohanad Shkoor、Stephen G. Newman

  DOI：10.1021/acscatal.7b00245

  日期：2017.3.3

  A palladium-catalyzed cross-coupling between aryl esters and anilines is reported, enabling access to diverse amides. The reaction takes place via activation of the C–O bond by oxidative addition with a Pd–NHC complex, which enables the use of relatively non-nucleophilic anilines that otherwise require stoichiometric activation with strong bases in order to react. High yields of aromatic, aliphatic

  据报道，钯催化的芳基酯和苯胺之间的交叉偶联，使得能够获得各种酰胺。反应是通过Pd-NHC络合物的氧化加成激活C-O键来进行的，这使得能够使用相对非亲核的苯胺，否则需要化学计量的活化才能使强碱发生反应。获得高产率的芳族，脂族和杂环产物。在存在和不存在催化剂的情况下评估了一系列活化酯，这表明催化方法大大增加了在不存在苛刻碱的情况下可用于酰胺键形成的亲电试剂的类型。
• Mapping out the Relative Influence of Hydrogen and Halogen Bonds in Crystal Structures of a Family of Amide-Substituted Pyridines
  作者：Amila M. Abeysekera、Victor W. Day、Abhijeet S. Sinha、Christer B. Aakeröy

  DOI：10.1021/acs.cgd.0c01086

  日期：2020.11.4

  Bz-I and 2Pyr-I, the primary hydrogen bonding resembled that of the other members of the family, indicating that the interactions mediated via the iodine atom were complementary to rather than competitive with the hydrogen bonds. Two polymorphs of 4Pyr-I were found, and in both forms, a halogen bond was formed with the N(py) acceptor which was engaged in N–H···N hydrogen bonds in the other members of

  以前已经在晶体工程策略中同时使用氢键和卤素键，以产生新的固体形式，并应用于例如制药和农业化学工业。不幸的是，要预测这些将如何在可能产生多种结构结果的系统中共存或竞争并不容易。为了解决这一挑战，我们研究了酰胺取代的吡啶家族的固态结构，该家族属于四个系列的N-（吡啶-2-基）苯甲酰胺（Bz），N-（吡啶-2-基） picolinamides（2Pyr），ñ - （吡啶-2-基）烟酰胺（3Pyr）和ñ - （吡啶-2-基）isonicotinamides（4Pyr），用三个不同的卤素原子（氯，溴和碘）官能化。我们分析了16种化合物的晶体结构，并确定了它们的主要分子间相互作用。在每个系列中，氯代和溴代化合物呈现出与未卤代母体相同的主要氢键相互作用。的Ñ -经由NH组装（吡啶-2-基）苯甲酰胺... N（PY）的合成子以形成二聚体，ñ - （吡啶-2-基）显示的分子内NH picolinamides
• Structural diversity, spectral characterization and computational studies of Cu(I) complexes with pyridylamide ligands
  作者：Ethan P. McMoran、Manuel N. Dominguez、Ethan M. Erwin、Douglas R. Powell、Gerard T. Rowe、Lei Yang

  DOI：10.1016/j.ica.2016.03.011

  日期：2016.5

  ) (2) and [Cu(4-ppa)(NCCH3)2]BF4 (5) displayed mononuclear structures with tetrahedral geometries on Cu(I) centers. Dinuclear complex [Cu2(2-pina)3(NCCH3)4](SbF6)2 (3) and tetranuclear cluster [Cu4(2-pina)4(NCCH3)4](SbF6)4 (4) were afforded from the same reaction in CH3CN and DMF, respectively. Detailed analysis of X-ray crystal structures and Hirshfeld surface maps suggested that the weak non-covalent

  吡啶酰胺配体N-2-乙酰氨基吡啶（Haap），N-（3-吡啶基）烟酰胺（3-pna），N-（2-吡啶基）异烟酰胺（2-pina）和N-（4合成并表征了-吡啶基）吡啶甲酸酰胺（4-ppa）。CuCl与Haap的去质子化形式反应生成具有一维聚合物结构的复合物[Cu2（aap）2] n（1）。配合物[Cu（3-pna）3（NCCH3）]（HF）（SbF6）（2）和[Cu（4-ppa）（NCCH3）2] BF4（5）在Cu（I）上显示具有四面体几何形状的单核结构中心。双核复合物[Cu2（2-pina）3（NCCH3）4]（SbF6）2（3）和四核簇[Cu4（2-pina）4（NCCH3）4]（SbF6）4（4）提供反应分别在CH3CN和DMF中进行。对X射线晶体结构和Hirshfeld表面图的详细分析表明，弱的非共价相互作用和反应溶剂对Cu（I）配合物的结构构象产生了协同作用。通过循环伏安法研究了
• Iodine-Promoted N-Acylation of Amines with Hydrazide: An Efficient Metal-Free Amidation
  作者：Keyume Ablajan、Long Tian、Qianwei Zhang

  DOI：10.1055/a-1838-9491

  日期：2022.10

  protocol for the amidation of hydrazide with amine has been developed by utilizing I2 as an oxidant under metal- and base-free conditions at room temperature. N-Acylation products of amines were obtained in good to excellent yields without using toxic reagents. This method is operationally straightforward and tolerates aliphatic/aromatic and primary/secondary amines with different hydrazides.

  通过在室温下在无金属和无碱条件下使用 I 2作为氧化剂，开发了一种用于酰肼与胺的酰胺化的有效方案。在不使用有毒试剂的情况下，以良好至极好的收率获得了胺的 N-酰化产物。该方法操作简单，可耐受脂肪族/芳香族和伯/仲胺与不同的酰肼。
• Synthesis and characterization of divalent metal complexes with bipyridylamide ligands
  作者：Ethan P. McMoran、Clement Mugenzi、Kyle Fournier、Mark Draganjac、Donavon Tony、Kwangkook Jeong、Douglas R. Powell、Lei Yang

  DOI：10.1080/00958972.2015.1122188

  日期：2016.2.1

  Reaction of N-(4-pyridyl)picolinamide (4-ppa), N-(4-pyridyl)nicotinamide (4-pna), N-(4-pyridyl)isonicotinamide (4-pina), and N-(2-pyridyl)isonicotinamide (2-pina) with divalent metal salts led to the formation of six new coordination complexes. The X-ray structure of [Zn(4-ppa)(2)Cl-2] (1) shows a mononuclear structure with interesting intermolecular hydrogen bonding interactions. [Zn(4-pna)(OAc)(2)](n) (2), Cu(4-pna)(OTf)(2)(DMF)(2)](n) (3), [Zn(4-pina)(DMF)(4)](OTf)(2)}(n) (4), [Fe(4-pina)(DMF)(4)](OTf)(2)}(n) (5), and [Cu(2-pina)(OTf)(2)(DMF)(2)](n) (6) are one-dimensional coordination polymers with conformational differences caused by the coordination donor disposition, which demonstrates the flexibility of the pyridylamide ligands in polymeric structures. Reflectance UV-visible spectra and thermal properties of the coordination polymers are also reported.[GRAPHICS]