N-(pyridin-4-yl)pyridin-3-amine | 33932-94-4

• 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-(pyridin-4-yl)pyridin-3-amine
• 英文别名: 3,4'-dipyridylamine；pyridin-3-yl-pyridin-4-yl-amine；[3]pyridyl-[4]pyridyl-amine；dpa；[3]Pyridyl-[4]pyridyl-amin；γ-(β-Pyridylamino)-pyridin；N-pyridin-4-ylpyridin-3-amine
• CAS: 33932-94-4
• 化学式: C₁₀H₉N₃
• mdl: MFCD00234632
• 分子量: 171.202
• InChiKey: VMGJZCQLGGREAV-UHFFFAOYSA-N

物化性质

• 熔点：
  154-155 °C
• 沸点：
  353.7±17.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 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：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(pyridin-4-yl)pyridin-3-amine 、 zinc(II) chloride 以 乙醇 为溶剂， 以66%的产率得到[Zn(3,4'-dipyridylamine)2Cl2]
  参考文献：
  名称：

  Novel supramolecular structures and theoretical calculation of Ag(I) and Zn(II) complexes based on a new dipyridylamine ligand

  摘要：

  A new ligand dpa (dpa = 3,4'-dipyridylamine) (1) has been designed and synthesized, which reacted with AgNO3 and ZnCl2, respectively, resulting in two new complexes, [Ag(dpa)(2)]NO3 (2) and [ZnCl2(dpa)(2)] (3). The complexes have been characterized by thermogravimetric analysis, spectroscopic techniques, and single crystal X-ray diffraction. 2 is one-dimensional (ID) helical chain structure formed by hydrogen bonding interaction, and the helices are connected by the electrostatic interaction between Ag(I) ions and O atoms from NO3-, leading to a two-dimensional (2D) supramolecular structure. For 3, the mononuclear [ZnCl2(dpa)(2)] is almost a regular tetrahedral configuration, which generates a dimeric structure constructed through N-(HCl)-Cl-... hydrogen bonds and pi-pi interactions between pyridine rings. The adjacent dimeric units extend further into two-dimensional rippled network structure by two kinds of hydrogen bonds (N-(HCl)-Cl-..., C-(HCl)-Cl-...) in different directions. On the basis of experiment, both two complexes were calculated by DFT-B3LYP/LANL2DZ in GAUSSIAN 03. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2005.07.016
• 作为产物：
  描述：

  4-氨基吡啶 、 3-吡啶硼酸频哪醇酯 在 copper diacetate 、 硼酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以59%的产率得到N-(pyridin-4-yl)pyridin-3-amine
  参考文献：
  名称：

  Chan-Lam 胺化的光谱研究：一种受机制启发的硼酸酯反应性解决方案

  摘要：

  我们报告了对 Chan-Lam 胺化反应的调查。光谱学、计算模型和晶体学的结合已经确定了关键中间体的结构，并允许呈现完整的机制描述，包括非循环抑制过程、胺和有机硼反应性问题的来源，以及竞争氧化的起源/原脱硼副反应。关键机制事件的识别使得开发出解决这些问题的简单方法：操纵 Cu(I) → Cu(II) 氧化和利用硼酸的三种协同作用，开发了通用催化 Chan-Lam 胺化，克服了这种有价值的转化长期存在且未解决的胺和有机硼限制。

  DOI：

  10.1021/jacs.6b12800

文献信息

• Jerchel; Jakob, Chemische Berichte, 1958, vol. 91, p. 1266,1272
  作者：Jerchel、Jakob

  DOI：——

  日期：——
• Zwart; Wibaut, Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 1081,1084
  作者：Zwart、Wibaut

  DOI：——

  日期：——
• P2X7 MODULATORS
  申请人：Janssen Pharmaceutica NV

  公开号：EP2970267B3

  公开（公告）日：2018-05-30
• Spectroscopic Studies of the Chan–Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity
  作者：Julien C. Vantourout、Haralampos N. Miras、Albert Isidro-Llobet、Stephen Sproules、Allan J. B. Watson

  DOI：10.1021/jacs.6b12800

  日期：2017.4.5

  of amine and organoboron reactivity issues, and the origin of competing oxidation/protodeboronation side reactions. Identification of key mechanistic events has allowed the development of a simple solution to these issues: manipulating Cu(I) → Cu(II) oxidation and exploiting three synergistic roles of boric acid has allowed the development of a general catalytic Chan-Lam amination, overcoming long-standing

  我们报告了对 Chan-Lam 胺化反应的调查。光谱学、计算模型和晶体学的结合已经确定了关键中间体的结构，并允许呈现完整的机制描述，包括非循环抑制过程、胺和有机硼反应性问题的来源，以及竞争氧化的起源/原脱硼副反应。关键机制事件的识别使得开发出解决这些问题的简单方法：操纵 Cu(I) → Cu(II) 氧化和利用硼酸的三种协同作用，开发了通用催化 Chan-Lam 胺化，克服了这种有价值的转化长期存在且未解决的胺和有机硼限制。
• Novel supramolecular structures and theoretical calculation of Ag(I) and Zn(II) complexes based on a new dipyridylamine ligand
  作者：Cai-Hua Zhou、Hai-Yan Zhu、Yao-Yu Wang、Ping Liu、Li-Jun Zhou、Dong-Sheng Li、Qi-Zhen Shi

  DOI：10.1016/j.molstruc.2005.07.016

  日期：2005.11

  A new ligand dpa (dpa = 3,4'-dipyridylamine) (1) has been designed and synthesized, which reacted with AgNO3 and ZnCl2, respectively, resulting in two new complexes, [Ag(dpa)(2)]NO3 (2) and [ZnCl2(dpa)(2)] (3). The complexes have been characterized by thermogravimetric analysis, spectroscopic techniques, and single crystal X-ray diffraction. 2 is one-dimensional (ID) helical chain structure formed by hydrogen bonding interaction, and the helices are connected by the electrostatic interaction between Ag(I) ions and O atoms from NO3-, leading to a two-dimensional (2D) supramolecular structure. For 3, the mononuclear [ZnCl2(dpa)(2)] is almost a regular tetrahedral configuration, which generates a dimeric structure constructed through N-(HCl)-Cl-... hydrogen bonds and pi-pi interactions between pyridine rings. The adjacent dimeric units extend further into two-dimensional rippled network structure by two kinds of hydrogen bonds (N-(HCl)-Cl-..., C-(HCl)-Cl-...) in different directions. On the basis of experiment, both two complexes were calculated by DFT-B3LYP/LANL2DZ in GAUSSIAN 03. (c) 2005 Elsevier B.V. All rights reserved.