N,N'-bis(3-aminopropyl)-2,6-pyridinedicarboxylic diamide | 148019-59-4

• 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(3-aminopropyl)-2,6-pyridinedicarboxylic diamide
• 英文别名: 2,6-bis(1-propanecarboxamido-3-amino)pyridine；2,6-bis(3-aminopropylaminocarbonyl)pyridine；2-N,6-N-bis(3-aminopropyl)pyridine-2,6-dicarboxamide
• CAS: 148019-59-4
• 化学式: C₁₃H₂₁N₅O₂
• 分子量: 279.342
• InChiKey: RDFXXMSGHBZHLU-UHFFFAOYSA-N

物化性质

• 沸点：
  598.8±50.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N'-bis(3-aminopropyl)-2,6-pyridinedicarboxylic diamide 在 cadmium(II) perchlorate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以63%的产率得到[2,6-bis(3-aminopropylaminocarbonyl)pyridino-N,N',N'',N''']cadmium(II) perchlorate
  参考文献：
  名称：

  具有大环配体的双核和多核过渡金属配合物。5. 不对称多齿大环席夫碱的新型配合物。分步合成

  摘要：

  2,6-双(3-氨基丙基氨基羰基)吡啶 (1) 与 4-叔丁基-2,6-二甲酰基苯酚和 2,5-二甲酰基吡咯在 Ba(ClO4)2 的存在下在 EtOH 中反应得到不对称的钡配合物大环席夫碱作为软配体和硬配体。化合物 1 与 Cu(OCOCMe3)2 的反应包括四氢嘧啶环的闭合，得到单核配合物，其结构通过 X 射线衍射分析表征。

  DOI：

  10.1023/b:rucb.0000030808.51647.f1
• 作为产物：
  描述：

  吡啶-2,6-二甲酸 在 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 75.0h， 生成 N,N'-bis(3-aminopropyl)-2,6-pyridinedicarboxylic diamide
  参考文献：
  名称：

  基于Bis-1,8-萘二甲酰亚胺二联体的Cu2 +离子选择性和灵敏荧光化学传感器。

  摘要：

  制备，表征了一系列新型荧光化学传感器5a - 5e，该传感器由两个氨基萘二甲酰亚胺荧光团和2,6-双（（N-氨基烷基）氨基羧基）吡啶组成，并表征了它们对重金属和过渡金属（HTM）离子的荧光特性。调查。化学传感器5c – 5e对Cu 2+离子具有其他选择性，对其他具有荧光猝灭作用（绿色至无色）的HTM离子具有较高的灵敏度。它清楚地表明，氨基萘二甲酰亚胺和5a - 5e的2,6-二羧基吡啶之间的连接基（二胺）的长度对于它们对Cu 2+的敏感性和选择性非常重要。 离子超过其他HTM离子。

  DOI：

  10.1002/cjoc.201180481

文献信息

• Bisphosphonate sequestering agents. Synthesis and preliminary evaluation for in vitro and in vivo uranium(VI) chelation
  作者：Marcin Sawicki、Delphine Lecerclé、Gérard Grillon、Béatrice Le Gall、Anne-Laure Sérandour、Jean-Luc Poncy、Théodorine Bailly、Ramon Burgada、Marc Lecouvey、Vincent Challeix、Antoine Leydier、Stephane Pellet-Rostaing、Eric Ansoborlo、Frédéric Taran

  DOI：10.1016/j.ejmech.2008.01.018

  日期：2008.12

  A library of bisphosphonate-based ligands was prepared using solution-phase parallel synthesis and tested for its uranium-binding properties. With the help of a screening method, based on a chromophoric complex displacement procedure, 23 dipodal and tripodal chelates bearing bisphosphonate chelating functions were found to display very high affinity for the uranyl ion and were selected for evaluation of their in vivo uranyl-removal efficacy. Among them, 11 ligands induced a huge modification of the uranyl biodistribution by deviating the metal from kidney and bones to liver. Among the other ligands, the most potent was the dipodal bisphosphonate 3C which reduced the retention of uranyl and increased its excretion by around 10% of the injected metal. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Cai, Li-Hua; Hu, Pei-Zhi; Du, Xiao-Lan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 3, p. 523 - 528
  作者：Cai, Li-Hua、Hu, Pei-Zhi、Du, Xiao-Lan、Zhang, Li-Xia、Liu, Yi

  DOI：——

  日期：——
• Synthesis, complexation and cyclisation reactions of a new acyclic diamide: observation of intramolecular ligand exchange in a structurally characterised nickel(II) complex
  作者：Sally Brooker、Geoffrey S Dunbar、Geoffrey B Jameson

  DOI：10.1016/s0277-5387(98)00338-6

  日期：1999.1

  A new acyclic diamide ligand, H(2)L1, has been prepared and characterised. H(2)L1, 2,6-bis(1-propanecarboxamido-3-amino)pyr is prepared from 2,6-dimethylpyridinedicarboxylate and excess I,3-diaminopropane. Nickel(II) complexes derived from H(2)L1 [Ni(L1+H)]X, are orange, square planar and diamagnetic (X=ClO4-, CF3SO3- or NO3-). A single-crystal X-ray analysis of [Ni(L1+H)]CLO4 confirmed that both of the amide groups are deprotonated and are bound to the nickel ion with a trans-amide configuration and that the remaining coordination sites are occupied by the pyridine nitrogen atom and one of the amine "arms". The second amine "arm" is protonated and participates in an array of hydrogen bonds in the solid state. In solution intramolecular exchange of the "arms" is observed on the NMR timescale. Three macrocycles have been prepared from this acyclic ligand. Reaction of H(2)L1 with 2,6-diacetylpyridine or 2,6-diformylpyridine, in the presence of a barium(II) template ion, results in two new unsymmetrical, amide-containing and potentially dinucleating macrocycles as the complexes [Ba(H(2)L2)](ClO4)(2) and [Ba (H(2)L3)] (ClO4)(2), respectively. In contrast to the template cyclisations, a symmetrical metal-free tetraamide macrocycle, H(2)L4, is produced from the direct cyclisation of H(2)L1 with 2,6-dimethylpyridinedicarboxylate. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Complexation of copper(II) with acyclic amide ligands: structure of an unexpected rearrangement product resulting from an intramolecular reaction of an amine with an amide
  作者：Sally Brooker、Geoffrey S. Dunbar、Paul G. Plieger

  DOI：10.1016/s0020-1693(00)00089-x

  日期：2000.6

  The copper(II) coordination chemistry of an acyclic diamide ligand, H(2)L1, has been investigated [H(2)L1 = 2,6-bis(1-propanecarboxamido-3-amino)pyridine]. Purple compounds, Cu(L1+H)NO3 and Cu(L1')OAc, are formed when H(2)L1 is reacted with copper(II) nitrate and copper(II) acetate, respectively. The latter complex was characterised by X-ray crystallography which revealed that an unexpected intramolecular dehydration reaction, between one of the amide groups in H(2)L1 and an amine group from the same 'arm', had resulted in the formation of an amidine group. The copper(II) ion is square pyramidal, with the four basal plane nitrogen donor atoms provided by the ligand (L1')(-) and the apical site occupied by an oxygen donor from an acetate ion. The two ligand types, (L1+H)(-) and (L1')(-), can be distinguished by cyclic voltammetry: as anticipated the Cu(L1+ H)NO3 complex (E-pa = +0.98 V, in H2O vs. SCE), with two coordinated amide nitrogen atoms, is more easily oxidised than the Cu(L1')OAc complex (E-pa = + 1.13 V, in H2O vs. SCE), in which there is only one coordinated amide nitrogen atom. (C) 2000 Elsevier Science S.A. All rights reserved.