Bis[di(2-pyridyl)methyl]amine | 211557-37-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Bis[di(2-pyridyl)methyl]amine
• 英文别名: bis(di-2-pyridzlmethyl)amine；Bis(di-2-pyridylmethyl)amine；N-(dipyridin-2-ylmethyl)-1,1-dipyridin-2-ylmethanamine
• CAS: 211557-37-8
• 化学式: C₂₂H₁₉N₅
• 分子量: 353.426
• InChiKey: WRBCOHJRQRHCKB-UHFFFAOYSA-N

物化性质

• 沸点：
  510.5±45.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Bis[di(2-pyridyl)methyl]amine 在 ferric nitrate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 1,3,3-Tris(2-pyridyl)-3H-imidazo[1,5-a]pyridin-4-ium nitrate
  参考文献：
  名称：

  Isolation and characterization of an oxidative degradation product of a polypyridine ligand

  摘要：

  讨论了多吡啶配体在氧化条件下易碎的成因。

  DOI：

  10.1039/a803255f
• 作为产物：
  描述：

  1,1-双(吡啶-2-基)甲胺 在 3 A molecular sieve 、 溶剂黄146 、 锌 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 生成 Bis[di(2-pyridyl)methyl]amine
  参考文献：
  名称：

  Preparation and Crystal Structures of Manganese, Iron, and Cobalt Complexes of the Bis[di(2-pyridyl)methyl]amine (bdpma) Ligand and Its Oxidative Degradation Product 1,3,3-Tris(2-pyridyl)-3H-imidazo[1,5-a]pyridin-4-ium (tpip); Origin of the bdpma Fragility

  摘要：

  The synthesis and structural characterization of manganese, iron, and cobalt complexes of bis[di(2-pyridyl)methyl]amine (bdpma) were investigated. The bdpma ligand can give rise to mono- or dimeric complexes. Moreover, bdpma can undergo oxidative degradation leading to 1,3,3-tris(2-pyridyl)-3H-imidazo[1,5-a]pyridin-4-ium (tpip) or to starting materials used for the preparation of bdpma. During attempts to prepare manganese, iron, or cobalt complexes of the tpip ligand, two classes of compounds were obtained. The first class corresponded to the tpip cation with a simple exchange of counterion and the second class led to a new type of complex, which involved a modification of tpip and contained the N-(di(2-pyridyl)methoxymethyl)(di(2-pyridyl)imine) (dpmmdpi) ligand. This work has allowed us to understand the fragility of the bdpma ligand, which is due to the easily activated benzylic C-H bonds in the a position to the heteroatom.

  DOI：

  10.1002/(sici)1521-3765(19990604)5:6<1766::aid-chem1766>3.0.co;2-z

文献信息

• Influence of the anion of FeIII salts on the product distribution in the oxidative degradation of a tetrapyridyl ligand
  作者：Michael Renz、Catherine Hemmert、Heinz Gornitzka、Bernard Meunier

  DOI：10.1039/a902907i

  日期：——

  investigation of corresponding iron(III) complexes has revealed the fragility of the BDPMA ligand. Different degradation products of the starting ligand have been crystallized and the distribution of these derivatives strongly depends on the nature of the anion in the iron(III) salts.

  我们将注意力集中在四吡啶基配体双[二（2-吡啶基）甲基]胺（BDPMA）上，以制备单核非血红素铁（III）配合物，作为氧化反应中的催化剂前体。对相应的铁（III）配合物的研究揭示了BDPMA配体的脆弱性。起始配体的不同降解产物已经结晶，这些衍生物的分布在很大程度上取决于铁（III）盐中阴离子的性质。
• Synthesis, characterization and crystal structures of copper(II) complexes containing multidentate polypyridine ligands †
  作者：Catherine Hemmert、Michael Renz、Heinz Gornitzka、Bernard Meunier

  DOI：10.1039/a906118e

  日期：——

  distorted trigonal bipyramidal, square pyramidal and octahedral geometries, respectively. FAB mass spectra and ESR spectra of crystalline samples and frozen solutions suggested that the overall structures are not modified for complexes 1–3 on going from the solid to the solution states.

  合成并结晶了四吡啶基配体双[二（2-吡啶基）甲基]胺的三种单核铜（II）配合物。相应的X射线晶体结构在金属离子周围显示出不同的几何形状，这主要是由铜（II）盐的阴离子配体的性质引起的。Cu（BDPMA）Cl 2 1，Cu（BDPMA）（SO 4）MeOH 2和[Cu（BDPMA）（BF 4）CH 3 CN] BF 43分别显示了扭曲的三角双锥体，方形锥体和八面体几何形状。晶体样品和冷冻溶液的FAB质谱和ESR光谱表明，从固体状态到溶液状态时，配合物1-3的整体结构没有改变。
• Oxidative degradation of chlorinated phenols catalyzed by a non-heme iron(III) complex
  作者：Catherine Hemmert、Michael Renz、Bernard Meunier

  DOI：10.1016/s1381-1169(98)00131-9

  日期：1999.1

  A new symmetric pentadentate ligand containing four pyridine groups, bis(di-2-pyridylmethyl)amine (BDPMA), has been synthesized in a good yield. The corresponding non-heme iron(III) complex, [Fe(BDPMA)](NO3)3, with potassium monopersulfate as oxidant, catalyzed the oxidative degradation of aromatic pollutants chlorinated phenols to yield the corresponding benzoquinones.

  一种新的对称的五齿配体，含有四个吡啶基，双（二-2-吡啶基甲基）胺（BDPMA），已经以高收率合成。以单过硫酸钾为氧化剂的相应的非血红素铁（III）络合物[Fe（BDPMA）]（NO 3）3催化芳香族污染物氯化酚的氧化降解，得到相应的苯醌。
• Synthesis of Bis[di(2-pyridyl)methyl]amine (BDPMA) by a Novel One-Pot Multi-Step Reductive Amination with Molecular Sieves and Zn/iPrOH
  作者：Michael Renz、Catherine Hemmert、Bernard Meunier

  DOI：10.1002/(sici)1099-0690(199807)1998:7<1271::aid-ejoc1271>3.0.co;2-q

  日期：1998.7

  Bis[di(2-pyridyl)methyl]amine (BDPMA) has been synthesized by refluxing di-2-pyridyl ketone and di-(2-pyridyl)methylamine in isopropanol in the presence of molecular sieves and acetic acid and subsequent reduction with zinc dust. The established methods for reductive amination, i.e. NaBH3CN, NaBH(OAc)(3) and NaBH4, failed in the synthesis of BDPMA due to a disfavored equilibrium towards the imine formation and therefore long reaction times were required, involving side reactions, The presented method can be used on large-scales and tolerates aromatic heterocycles as functional groups.