6-[(3-pyridylmethylamino)carbonyl]pyridine-2-carboxylic acid methyl ester | 1172132-42-1

• 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: 6-[(3-pyridylmethylamino)carbonyl]pyridine-2-carboxylic acid methyl ester
• 英文别名: N-6-[(3-pyridylmethylamino)carbonyl]pyridine-2-carboxylicacid methyl ester；Methyl 6-(pyridin-3-ylmethylcarbamoyl)pyridine-2-carboxylate
• CAS: 1172132-42-1
• 化学式: C₁₄H₁₃N₃O₃
• 分子量: 271.276
• InChiKey: BTBNUCGFPUDJAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 6-[(3-pyridylmethylamino)carbonyl]pyridine-2-carboxylic acid methyl ester 以 甲醇 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  Building blocks for coordination polymers: self-assembled cleft-like and planar discrete metallo-macrocyclic complexes

  摘要：

  我们利用柔性酰胺配体 N-6-[(3-吡啶基甲基氨基)羰基]吡啶-2-羧酸（L1-CH3）及其刚性更强的类似物 N-6-[(3-吡啶基氨基)羰基]吡啶-2-羧酸（L3-CH3）制备了离散的双核金属大环配合物。配体 L1-CH3 和 L3-CH3 的离散双核金属大环配合物的通式为[Cu2(L1-CH3)2(X)2(Y)2]（7，X = NO3；8，X = Cl，Y = H2O；9，X = ClO4，Y = CH3OH）和 [Cu2(L3-CH3)2(X)2(Y)2]（10，X = NO3，Y = H2O；11，X = ClO4，Y = CH3OH）。对于含有较柔性链节 L1-CH3 的复合物 7-9，这些复合物呈裂隙状，并在亚甲基间隔处铰接，这使得裂隙可以扩大和收缩，以适应固态中不同的堆积模式。相比之下，刚性连接 L3-CH3 可产生近似平面的金属大环结构。这些金属大环化合物可能是配位聚合物的有用构件。

  DOI：

  10.1039/c2dt12320g
• 作为产物：
  描述：

  3-氨甲基吡啶 、 吡啶-2.6-二羧酸二甲酯 以 甲苯 为溶剂， 反应 24.0h， 以59%的产率得到6-[(3-pyridylmethylamino)carbonyl]pyridine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Syntheses and studies of flexible amide ligands: a toolkit for studying metallo-supramolecular assemblies for anion binding

  摘要：

  The syntheses of seven flexible bidentate bis-pyridyl diamide and four monodentate pyridyl amide ligands containing central amide units are described. The bis-pyridyl ligands were prepared in one step from commercially available compounds in moderate to good yield. These compounds all possess external metal coordinating pyridyl groups and internal amide functionalities, with the potential to bind anions. Crystal structures of six of the bis-pyridyl diamide ligands are described. The four compounds with xylene cores N,N'-[1,3-phenylenebis(methylene)]bis-3-pyridinecarboxamide 1, N,N'-[1,3-phenylenebis(methylene)]bis-4-pyridinecarboxamide 2, N,N'-[1,4-phenylenebis(methylene)]bis-3-pyridinecarboxamide 3 and N,N'-[1,4-phenylenebis(methylene)]bis-4-pyridinecarboxamide 4 crystallize with extensive amide N-H center dot center dot center dot O=C hydrogen bonding between the diamide compounds, giving rise to two and three dimensional hydrogen bonded networks. N,N'-Bis(3-pyridylmethyl)benzene-1,3-dicarboxamide 5, the only compound with the amide groups directly attached to a central benzene core, was not able to be crystallised. N,N'-2,6-Bis(3-pyridylmethyl)pyridine dicarboxamide 6 and N,N'-2,6-bis(4-pyridylmethyl)pyridine dicarboxamide 7 have a mismatch of hydrogen bond donor and acceptor regions preventing ready involvement of the amide NH groups in network formation. For comparison we also prepared compounds N,N'-2'-propyl-6-(3-pyridylmethyl)pyrid me dicarboxamide 10 and N,N'-2'-propyl-6-(4-pyridylmethyl)pyridine dicarboxamide 11 with two amide groups but only the one external donor pyridyl moiety, and compounds N-6-[(3-pyridylmethyl amino)carbonyl]-2-pyridinecarboxylic acid methyl ester 8 and N-6-[(4-pyridylmethylamino)-carbonyl] -2-pyridinecarboxylic acid methyl ester 9, which have only the one amide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.031

文献信息

• Self-assembled metallo-macrocycle based coordination polymers with unsymmetrical amide ligands
  作者：Maisara Abdul-Kadir、Lyall R. Hanton、Christopher J. Sumby

  DOI：10.1039/c1dt10853k

  日期：——

  A series of metallo-macrocyclic based coordination polymers has been prepared from flexible amide ligands N-6-[(3-pyridylmethylamino)carbonyl]-pyridine-2-carboxylic acid (L1-CH3) and N-6-[(4-pyridylmethylamino)carbonyl]-pyridine-2-carboxylic acid (L2-CH3). In all but one case, self-assembled dinuclear metallo-macrocyclic units form the basis of the polymeric structures, whereby discrete metal centres, and dinuclear or trinuclear clusters, are linked by the self-assembled macrocycles to give 1D and 2D coordination polymers. In one instance, a 1D coordination polymer is formed in a reaction carried out under ambient conditions; when the same reaction is conducted under solvothermal conditions a 2D structure is formed. In all but two of these structures, the polymeric chains and nets are close-packed within the crystals. In the case of a 6,3-connected 2D coordination polymer [Cd3(L2-CH3)3(NO3)(L2)(CH3OH)](NO3)2·12½H2O}n (9), small oval channels percolate down the a-axis of the unit cell.

  以柔性酰胺配体 N-6-[(3-吡啶基甲基氨基)羰基]-吡啶-2-羧酸（L1-CH3）和 N-6-[(4-吡啶基甲基氨基)羰基]-吡啶-2-羧酸（L2-CH3）为基础，制备了一系列金属大环配位聚合物。除一种情况外，自组装的双核金属大环单元构成了聚合物结构的基础，离散的金属中心和双核或三核簇通过自组装大环连接起来，形成一维和二维配位聚合物。其中一种情况是，在环境条件下进行的反应形成了一维配位聚合物；而在溶热条件下进行的相同反应则形成了二维结构。在所有这些结构中，除两种结构外，聚合物链和网都紧密地排列在晶体中。在 6,3 连接的二维配位聚合物[Cd3(L2-CH3)3(NO3)(L2)(CH3OH)](NO3)2-12½H2O}n (9)中，小的椭圆形通道沿着单胞的 a 轴向下渗透。
• Syntheses and studies of flexible amide ligands: a toolkit for studying metallo-supramolecular assemblies for anion binding
  作者：Christopher J. Sumby、Lyall R. Hanton

  DOI：10.1016/j.tet.2009.04.031

  日期：2009.6

  The syntheses of seven flexible bidentate bis-pyridyl diamide and four monodentate pyridyl amide ligands containing central amide units are described. The bis-pyridyl ligands were prepared in one step from commercially available compounds in moderate to good yield. These compounds all possess external metal coordinating pyridyl groups and internal amide functionalities, with the potential to bind anions. Crystal structures of six of the bis-pyridyl diamide ligands are described. The four compounds with xylene cores N,N'-[1,3-phenylenebis(methylene)]bis-3-pyridinecarboxamide 1, N,N'-[1,3-phenylenebis(methylene)]bis-4-pyridinecarboxamide 2, N,N'-[1,4-phenylenebis(methylene)]bis-3-pyridinecarboxamide 3 and N,N'-[1,4-phenylenebis(methylene)]bis-4-pyridinecarboxamide 4 crystallize with extensive amide N-H center dot center dot center dot O=C hydrogen bonding between the diamide compounds, giving rise to two and three dimensional hydrogen bonded networks. N,N'-Bis(3-pyridylmethyl)benzene-1,3-dicarboxamide 5, the only compound with the amide groups directly attached to a central benzene core, was not able to be crystallised. N,N'-2,6-Bis(3-pyridylmethyl)pyridine dicarboxamide 6 and N,N'-2,6-bis(4-pyridylmethyl)pyridine dicarboxamide 7 have a mismatch of hydrogen bond donor and acceptor regions preventing ready involvement of the amide NH groups in network formation. For comparison we also prepared compounds N,N'-2'-propyl-6-(3-pyridylmethyl)pyrid me dicarboxamide 10 and N,N'-2'-propyl-6-(4-pyridylmethyl)pyridine dicarboxamide 11 with two amide groups but only the one external donor pyridyl moiety, and compounds N-6-[(3-pyridylmethyl amino)carbonyl]-2-pyridinecarboxylic acid methyl ester 8 and N-6-[(4-pyridylmethylamino)-carbonyl] -2-pyridinecarboxylic acid methyl ester 9, which have only the one amide. (C) 2009 Elsevier Ltd. All rights reserved.
• Building blocks for coordination polymers: self-assembled cleft-like and planar discrete metallo-macrocyclic complexes
  作者：Maisara Abdul-Kadir、Lyall R. Hanton、Christopher J. Sumby

  DOI：10.1039/c2dt12320g

  日期：——

  Discrete dinuclear metallo-macrocyclic complexes have been prepared from the flexible amide ligand N-6-[(3-pyridylmethylamino)carbonyl]pyridine-2-carboxylic acid (L1-CH3), and its more rigid analogue, N-6-[(3-pyridylamino)carbonyl]pyridine-2-carboxylic acid (L3-CH3). With ligands L1-CH3 and L3-CH3, discrete dinuclear metallo-macrocyclic complexes with the generic formula [Cu2(L1-CH3)2(X)2(Y)2] (7, X = NO3; 8, X = Cl, Y = H2O; 9, X = ClO4, Y = CH3OH) and [Cu2(L3-CH3)2(X)2(Y)2] (10, X = NO3, Y = H2O; 11, X = ClO4, Y = CH3OH) are obtained. For complexes 7–9, containing the more flexible link L1-CH3, these complexes are cleft-shaped and hinged at the methylene spacer, which allows the cleft to widen and contract to accommodate different packing modes in the solid-state. In contrast, the rigid link L3-CH3 gives near planar metallo-macrocyclic structures. These metallo-macrocyclic compounds may be useful building blocks for coordination polymers.

  我们利用柔性酰胺配体 N-6-[(3-吡啶基甲基氨基)羰基]吡啶-2-羧酸（L1-CH3）及其刚性更强的类似物 N-6-[(3-吡啶基氨基)羰基]吡啶-2-羧酸（L3-CH3）制备了离散的双核金属大环配合物。配体 L1-CH3 和 L3-CH3 的离散双核金属大环配合物的通式为[Cu2(L1-CH3)2(X)2(Y)2]（7，X = NO3；8，X = Cl，Y = H2O；9，X = ClO4，Y = CH3OH）和 [Cu2(L3-CH3)2(X)2(Y)2]（10，X = NO3，Y = H2O；11，X = ClO4，Y = CH3OH）。对于含有较柔性链节 L1-CH3 的复合物 7-9，这些复合物呈裂隙状，并在亚甲基间隔处铰接，这使得裂隙可以扩大和收缩，以适应固态中不同的堆积模式。相比之下，刚性连接 L3-CH3 可产生近似平面的金属大环结构。这些金属大环化合物可能是配位聚合物的有用构件。