N,N-bis[(2-pyridyl)methyl]-1-(2-pyridyl)ethanamine | 86894-18-0

• 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-pyridyl)methyl]-1-(2-pyridyl)ethanamine
• 英文别名: 1-(2-pyridyl)ethyl-bis-(2-pyridylmethyl)amine；(1S)-1-pyridin-2-yl-N,N-bis(pyridin-2-ylmethyl)ethanamine
• CAS: 86894-18-0
• 化学式: C₁₉H₂₀N₄
• 分子量: 304.395
• InChiKey: ALEHUUZFZJQJSS-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-bis[(2-pyridyl)methyl]-1-(2-pyridyl)ethanamine 、 cadmium(II) iodide 以 甲醇 为溶剂， 以86.6%的产率得到[Cd(N,N-bis[(2-pyridyl)methyl]-1-(2-pyridyl)ethanamine)I2]
  参考文献：
  名称：

  Solid State and Solution Characterization of Chiral, Conformationally Mobile Tripodal Ligands

  摘要：

  The synthesis of the ligands N,N-bis[(2-pyridyl)methyl]-1-(2-pyridyl)ethanamine (1, alpha-MeTPA), N,N-bisl[6-phenyl-2-pyridyl)methyl]-1-(2-pyridyl)ethanamine (2, alpha-MePh(2)TPA), N,N-bis[(2-quinolyl)methyl]-1-(2-pyridyl)ethanamine, (3, alpha-MeBQPA), and N,N-bis[(2-pyridyl)]methyl(phenyl)(2-pyridyl)methanamine (4, alpha-PhTPA) is described. The ligands form chiral, pseudo C-3-symmetric complexes with Zn-II and Cu-II salts that possess an available electrophilic coordination site. X-ray crystallographic structures of the complexes [Zn(alpha-MeTPA)Cl] (ClO4), [Zn(alpha-MeBQPA)Cl](ClO4), and [Zn(alpha-PhTPA)Cl](ClO4) show that the spatial arrangement of the three pyridyl groups resembles a propeller whose directional sense is controlled by a substituent on one methylene arm. Chiroptical measurements provide supporting information that the complexes maintain similar structures in solution. Monte Carlo/stochastic dynamics (MC/SD) simulations of the [Zn(L)Cl](+) complexes indicate that only two conformers are populated at normal temperatures, suggest the presence of a synchronicity in the movement of the heteroaromatic rings during conformer interconversions, and provide an estimate of the energy difference between the conformers.

  DOI：

  10.1021/ic9803098
• 作为产物：
  描述：

  碘甲烷 、 三(2-吡啶基甲基)胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以94 %的产率得到N,N-bis[(2-pyridyl)methyl]-1-(2-pyridyl)ethanamine
  参考文献：
  名称：

  三(2-吡啶甲基)胺直接苄基官能化的新型配体

  摘要：

  三-(2-吡啶基甲基)胺（TPA 或 TPMA）是基于聚吡啶的配体，由于其能够与多种金属形成稳定的四齿配合物，广泛用于催化和超分子化学。未取代的配体也可商购，可通过甲基吡啶的连续烷基化或通过吡啶醛的还原胺化来合成。在本文中，我们报告了一种新的合成方法，该方法可以对这些配体在苄基位置进行后功能化。这种新颖的衍生化策略除了提供新颖结构和功能的合成途径外，还用于制备一系列金属配合物，并在光化学析氢中进行了测试。

  DOI：

  10.1039/d4dt02022g

文献信息

• Hoejland, Frede; Toftlund, Hans; Yde-Andersen, Steen, Acta chemica Scandinavica. Series A: Physical and inorganic chemistry, 1983, vol. 37, p. 251 - 258
  作者：Hoejland, Frede、Toftlund, Hans、Yde-Andersen, Steen

  DOI：——

  日期：——
• Solid State and Solution Characterization of Chiral, Conformationally Mobile Tripodal Ligands
  作者：James W. Canary、Craig S. Allen、Jesus M. Castagnetto、Yu-Hung Chiu、Paul J. Toscano、Yihan Wang

  DOI：10.1021/ic9803098

  日期：1998.11.1

  The synthesis of the ligands N,N-bis[(2-pyridyl)methyl]-1-(2-pyridyl)ethanamine (1, alpha-MeTPA), N,N-bisl[6-phenyl-2-pyridyl)methyl]-1-(2-pyridyl)ethanamine (2, alpha-MePh(2)TPA), N,N-bis[(2-quinolyl)methyl]-1-(2-pyridyl)ethanamine, (3, alpha-MeBQPA), and N,N-bis[(2-pyridyl)]methyl(phenyl)(2-pyridyl)methanamine (4, alpha-PhTPA) is described. The ligands form chiral, pseudo C-3-symmetric complexes with Zn-II and Cu-II salts that possess an available electrophilic coordination site. X-ray crystallographic structures of the complexes [Zn(alpha-MeTPA)Cl] (ClO4), [Zn(alpha-MeBQPA)Cl](ClO4), and [Zn(alpha-PhTPA)Cl](ClO4) show that the spatial arrangement of the three pyridyl groups resembles a propeller whose directional sense is controlled by a substituent on one methylene arm. Chiroptical measurements provide supporting information that the complexes maintain similar structures in solution. Monte Carlo/stochastic dynamics (MC/SD) simulations of the [Zn(L)Cl](+) complexes indicate that only two conformers are populated at normal temperatures, suggest the presence of a synchronicity in the movement of the heteroaromatic rings during conformer interconversions, and provide an estimate of the energy difference between the conformers.
• 10.1039/d4dt02022g
  作者：Zardi, Paolo、Piękoś, Justyna、Bravin, Carlo、Wurst, Klaus、Droghetti, Federico、Natali, Mirco、Licini, Giulia、Zambon, Alfonso、Zonta, Cristiano

  DOI：10.1039/d4dt02022g

  日期：——

  a picoline or by reductive amination of a pyridine aldehyde. In this article, we report a novel synthetic method which opens to the post-functionalisation of these ligands in the benzylic position. This novel derivatization strategy, beside providing synthetic access to novel structures and functions, has been used to prepare a series of metal complexes which have been tested in photochemical hydrogen

  三-(2-吡啶基甲基)胺（TPA 或 TPMA）是基于聚吡啶的配体，由于其能够与多种金属形成稳定的四齿配合物，广泛用于催化和超分子化学。未取代的配体也可商购，可通过甲基吡啶的连续烷基化或通过吡啶醛的还原胺化来合成。在本文中，我们报告了一种新的合成方法，该方法可以对这些配体在苄基位置进行后功能化。这种新颖的衍生化策略除了提供新颖结构和功能的合成途径外，还用于制备一系列金属配合物，并在光化学析氢中进行了测试。