N,N'-bis(2-(2-pyridyl)ethyl)-2,6-pyridinedicarboxamide | 147863-46-5

• 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,N'-bis(2-(2-pyridyl)ethyl)-2,6-pyridinedicarboxamide
• 英文别名: N,N'-bis(2-(2-pyridyl)ethyl)pyridine-2,6-dicarboxamide；N,N'-bis[2-(2-pyridyl)ethyl]pyridine-2,6-dicarboxamide；N,N-bis(2-(2-pyridyl)ethyl)pyridine-2,6-dicarboxamide；N,N-bis[2-(pyridyl)ethyl]-pyridine-2,6-dicarboxamide；N,N'-bis[2-(2-pyridyl)ethyl]-2,6-pyridinedicarboxamide；2-N,6-N-bis(2-pyridin-2-ylethyl)pyridine-2,6-dicarboxamide
• CAS: 147863-46-5
• 化学式: C₂₁H₂₁N₅O₂
• 分子量: 375.43
• InChiKey: LKTGVWCCBDWMQA-UHFFFAOYSA-N

物化性质

• 沸点：
  693.7±55.0 °C(predicted)
• 密度：
  1.234±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2-(2-pyridyl)ethyl)-2,6-pyridinedicarboxamide 在 Co-salt 、 OH(-) 作用下， 以 not given 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, Properties, and Structure of a Stable Cobalt(III) Alkyl Peroxide Complex and Its Role in the Oxidation of Cyclohexane

  摘要：

  Three cobalt(II) complexes of Py(3)PH(2) (H's are the dissociable amide H's), a strong-field ligand with two peptide groups, have been synthesized. They are [Co(Py(3)P)(H2O)]ClO4 . H2O (6), [Co(Py(3)P)(OH)] (7), and [Co(Py(3)P)(OO(t)Bu)].2CH2Cl2 (8). Complex 6 crystallizes in the monoclinic space group C2 with a = 22.695(6) Angstrom, b = 10.284(2) Angstrom, c = 10.908(3) Angstrom, alpha = 90 degrees, beta = 112.17(2)degrees, gamma = 90 degrees, V = 2357.7(10) Angstrom(3) and Z = 4. Its structure has been refined to R = 3.91% on the basis of 1844 I > 2 sigma(I) data. Complex 8 crystallizes in the monoclinic space group P2(1)/n with a = 16.720(4) Angstrom, b = 10.641(3) Angstrom, c = 16.776(3) Angstrom, alpha = 90 degrees, beta = 99.76(2)degrees, gamma = 90 degrees, V = 2941.5(12) Angstrom(3), and Z = 4. The structure of 8 has been refined to R = 6.37% on the basis of 4776 I > 2 sigma(I) reflections. In all three complexes, the doubly deprotonated Py(3)P(2-) ligand binds the cobalt(III) center in a pentadentate fashion with five nitrogens situated in two deprotonated amido groups and three pyridine rings. The aqua complex 6 can easily be converted into the hydroxo complex 7 by the addition of 1 equiv of base. The transformation 6 <-> 7 is reversible, and the pK(a) of the coordinated water molecule in 6 is 7. Complex 8 is the first example of a structurally characterized Co(III) alkyl peroxide complex that contains two deprotonated amido groups bonded to the metal center. Like a few alkyl peroxide complexes of tervalent cobalt, 8 oxidizes alkanes upon thermal decomposition. When cyclohexane is used as the substrate, cyclohexanol, cyclohexanone, and cyclohexyl chloride are the products. Complex 7 is the intermediate in the formation of 8 and is also the thermal decomposition product of 8. In single turnover oxidation of cyclohexane by 8 at the optimum temperature of 80 degrees C, a maximum yield of 59% of the oxidized products is obtained. The mechanism of cyclohexane oxidation by 8 involves exclusive homolytic scission of the O-O bond in 8. The (t)BuO(.) radicals generated in such a process abstract an ii atom from cyclohexane to afford cyclohexyl radicals, which in turn react with dioxygen and produce cyclohexanol and cyclohexanone presumably via a Russell-type termination reaction. The oxidation of cyclohexane by 8 can be either stoichiometric or catalytic. In the presence of excess TBHP, 8 affords more oxidized products, indicating multiple turnovers.

  DOI：

  10.1021/ic960500m
• 作为产物：
  描述：

  吡啶-2,6-二甲酸 在 氯化亚砜 、 三乙胺 作用下， 反应 6.0h， 生成 N,N'-bis(2-(2-pyridyl)ethyl)-2,6-pyridinedicarboxamide
  参考文献：
  名称：

  新吡啶羧酰胺配体及其与铜（II）的络合。单核，二核，三核和四核铜配合物的X射线晶体结构

  摘要：

  七个新的吡啶二甲酰胺 配体H 2 L 1–7是通过缩合反应合成的，包括吡啶-2,6-二羧酸（H 2 dipic），吡啶-2,6-二羰基二氯化物 或者 2,6-二氨基吡啶 带有杂环 胺 或者 羧酸前体。的晶体学分析N，N'-双（2-吡啶基）吡啶-2,6-二甲酰胺一水合物（H 2 L 8 ·H 2 O），N，N′-双[2-（2-吡啶基）甲基]吡啶-2，6-二甲酰胺和N，N'-双[2-（2-吡啶基）乙基]吡啶-2,6-二甲酰胺一水合物 揭示了广泛的分子内氢键相互作用。 2,6-双（吡嗪-2-羧酰胺基）吡啶（H 2 L 6）和2,6-双（吡啶-2-甲酰胺基）吡啶（H 2 L 7）与一水合乙酸铜（II）得到tricopper（II）配合物[铜3（L）2（μ 2 -OAc）2 ]。X射线晶体学 确认酰胺的去质子化 氮原子并且（L 6,7）2− 配体和醋酸根阴离子保持3铜（II）离子在大致线性的方式。H

  DOI：

  10.1039/b316519a

文献信息

• Ruthenium Nitrosyls Derived from Polypyridine Ligands with Carboxamide or Imine Nitrogen Donor(s):  Isoelectronic Complexes with Different NO Photolability
  作者：Michael J. Rose、Apurba K. Patra、Eric A. Alcid、Marylin M. Olmstead、Pradip K. Mascharak

  DOI：10.1021/ic0620945

  日期：2007.3.1

  coordination structures of 1 and 2 are very similar except that in 2, a carboxamido nitrogen is coordinated to the ruthenium center in place of an imine nitrogen in case of 1. In 3 and 4, the ruthenium center is coordinated to two carboxamido nitrogens in the equatorial plane and the bound NO is trans to a pyridine nitrogen (in 3) and chloride (in 4), respectively. Complexes 1-3 contain N6 donor set, and the

  作为我们寻找光活性钌亚硝酰基的一部分，已经合成了一组RuNO} 6亚硝酰基并对其结构进行了表征。在该组中，第一个亚硝酰基[（SBPy3）Ru（NO）]（BF4）3（1）衍生自聚吡啶希夫碱配体SBPy3，而其余三个亚硝酰基衍生自包含一个（[[ PaPy3）Ru（NO）]（ ）2（2））或两个[[（Py3P）Ru（NO）] （3）和[（Py3P）Ru（NO）（Cl）]（4））羧酰胺基（s）。1和2的配位结构非常相似，不同之处在于，在2中，一个羧酰胺基氮与钌中心配位，而不是亚胺氮（在1中）。在3和4中，钌中心被配位至两个羧酰胺基配位。赤道平面和结合的NO分别转化为吡啶氮（在3中）和氯化物（在4中）。配合物1-3包含N6供体组，并且NO拉伸频率（nuNO）与NO键距很好地相关。所有四个抗磁性RuNO}（6）亚硝酰基均具有光活性，并且在用低强度（5-10 mW）紫外线照射时会迅速释放N
• Synthesis, structural characterization, and anion binding studies of bisamide functionalized molecular clefts
  作者：Nafisah Mansor、Hafiza Mohamed Zuki、Uwaisulqarni M. Osman、Maisara Abdul Kadir

  DOI：10.1016/j.molstruc.2023.137410

  日期：2024.4

  The utilization of amide functional groups as anion-binding sites in the structure of synthetic anion receptors has received significant attention. In this study, three new compounds, namely, ′-bis(2-(pyridin-2-yl)ethyl)pyridine-2,6-dicarboxamide (), ′-bis(2-(pyridin-3-yl)ethyl)pyridine-2,6-dicarboxamide (), and ′-bis(2-(pyridin-4-yl)ethyl)pyridine-2,6-dicarboxamide (), have been successfully synthesized

  利用酰胺官能团作为合成阴离子受体结构中的阴离子结合位点已受到广泛关注。本研究中发现了三个新化合物，即'-双(2-(吡啶-2-基)乙基)吡啶-2,6-二甲酰胺()、'-双(2-(吡啶-3-基)乙基)已成功合成吡啶-2,6-二甲酰胺()和'-双(2-(吡啶-4-基)乙基)吡啶-2,6-二甲酰胺()。使用傅里叶变换红外光谱、气相色谱-质谱、氢和碳核磁共振光谱、元素分析和紫外-可见 (UV-Vis) 光谱等光谱技术的组合对这些化合物进行了全面表征。采用紫外-可见滴定法和荧光滴定法进一步研究了这些化合物与氯离子、硝酸根、铬酸根和磷酸根等阴离子结合的潜力，结果表明该化合物具有很高的结合能力。与其他研究的主体和分析物相比，氯离子、铬酸根和磷酸根阴离子。这为未来双酰胺化合物作为阴离子传感材料的进一步应用提供了良好的机会。
• Carboxamido Nitrogens Are Good Donors for Fe(III):  Syntheses, Structures, and Properties of Two Low-Spin Nonmacrocyclic Iron(III) Complexes with Tetracarboxamido-N Coordination
  作者：Dana S. Marlin、Marilyn M. Olmstead、Pradip K. Mascharak

  DOI：10.1021/ic981461c

  日期：1999.6.1

  Two nonmacrocyclic ligands with pyridine and carboxamide nitrogens as donors readily form his complexes of the type [(FeL2)-L-III](+) in which the Fe(III) centers exhibit preference for coordination to carboxamido nitrogens over pyridine nitrogens. These Fe(III) complexes with deprotonated carboxamido nitrogens are very stable in water.
• Multidentate N-heterocyclic podand ligand. Efficient oxygenation of phenols catalyzed by novel cobalt complex
  作者：Toshiyuki Moriuchi、Toshikazu Hirao、Takuji Ishikawa、Yoshiki Ohshiro、Isao Ikeda

  DOI：10.1016/1381-1169(94)00164-2

  日期：1995.1

  An efficient catalytic system for oxygenation of phenols to the p- or o-quinones with molecular oxygen was achieved by utilization of a complex catalyst consisting of Co(OAc)(2) and the multidentate N-heterocyclic podand ligand, N,N'-bis-2-(2-pyridyl) ethyl)-2,6-pyridinedicarboxamide.
• Synthesis, Structure, and Properties of {<i>N</i>,<i>N‘</i>- Bis[2-(2-pyridyl)ethyl]pyridine-2,6-dicarboxamido}copper(II)
  作者：Ferman A. Chavez、Marilyn M. Olmstead、Pradip K. Mascharak

  DOI：10.1021/ic9512136

  日期：1996.1.1

  The Cu(II) complex of N,N'-bis(2-(2-pyridyl)ethyl)-pyridine-2,6-dicarboxamide, a designed ligand with two amide moieties, has been isolated and structurally characterized. The copper center in this distorted square-pyramidal complex is coordinated to two deprotonated amido N donors and is situated 0.41 Angstrom above the mean basal plane. Such distortion results in a low A parallel to value of 154 G.