N,N-bis(6-methylpyridin-2-ylmethyl)benzylamine | 252328-39-5

• 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(6-methylpyridin-2-ylmethyl)benzylamine
• 英文别名: N-Benzyl-N,N-di(6-methyl-2-pyridylmethyl)amine；N-benzyl-N,N-bis(6-methyl-2-pyridylmethyl)amine；N-benzyl-N,N-bis[(6-methyl)pyrid-2-ylmethyl]amine；bis(6-methylpyridin-2-ylmethyl)benzylamine；bis(2-methyl-6-pyridylmethyl)benzylamine；N,N-bis[(6-methylpyridin-2-yl)methyl]-1-phenylmethanamine
• CAS: 252328-39-5
• 化学式: C₂₁H₂₃N₃
• 分子量: 317.434
• InChiKey: QQPOYONVEMZUST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-bis(6-methylpyridin-2-ylmethyl)benzylamine 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  由具有苯基硫醚的N（S）s型配体稳定的氢过氧-铜（II）配合物。

  摘要：

  DOI：

  10.1021/ja010689n
• 作为产物：
  描述：

  2-(氯甲基)-6-甲基吡啶盐酸盐 、 苄胺 在 水 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以36%的产率得到N,N-bis(6-methylpyridin-2-ylmethyl)benzylamine
  参考文献：
  名称：

  Selective Oxidation of [RhI(cod)]+ by H2O2 and O2

  摘要：

  New, five-coordinate Z,Z-1,5-cyclooctadiene (cod) complexes ['N-3'Rh-1(cod)](+) have been structurally characterised by NMR spectroscopy and X-ray diffraction ('N-3' = tridentate cyclic triamine or podal pyridine-amine-pyridine ligand). Their electrochemical oxidation and their oxygenation by H2O2 and O-2 have been investigated. The sigma-donor capacity of ligand 'N-3' in ['N-3'Rh-1(cod)](+) strongly influences the electrochemical oxidation potential and the C-13 chemical shift of the cod double bond. The relative sigma-donor strength of the individual amine (N-amine(R)) and pyridine (N-Py) nitrogens in the pyridine-amine-pyridine ligands, N-amine(H) > N-Py > N-Py.(Me) > N-amine(Bu) congruent to N-amine(Bz), is largely determined by steric repulsions. The cod complexes are selectively oxygenated by H2O2, and in one case by O-2 to rhodium(III)oxabicyclononadiyl complexes which rearrange to rhodium(III)hydroxycyclooctenediyl complexes. Oxygenation of cod to an oxabicyclononadiyl fragment and subsequent rearrangement to a hydroxycyclooctenediyl fragment are both thought to proceed via a 2-rhodaoxetane intermediate. Oxygenation of ['N-3'Rh-1(cod)](+) by H2O2 is relatively independent of the ligand and the solvent, and proceeds instantaneously and selectively. Oxygenation of ['N-3'Rh-1(cod)](+) by O-2 is greatly influenced by both the ligand and the solvent. Entirely selective oxidation by O-2 could only be obtained for 'N-3'= N,N-di(2-pyridylmethyl)amine (BPA) in CH2Cl2. Oxygenation by O-2 in CH2Cl2 requires one mole of O-2 per mole of [(BPA)Rh-1(cod)](+), is catalysed by acid and is likely to proceed by mononuclear activation of dioxygen. For both the cyclic triamine ligands and the podal pyridine-amine-pyridine ligands, the cod complexes with the lowest oxidation potentials are the most reactive and the most selective in oxygenation by O-2. Oxidation of the analogous 1,5-hexadiene (hed) complexes ['N-3'Rh-1(hed)](+) by either H2O2 or O-2 results in elimination of hed.

  DOI：

  10.1002/(sici)1521-3765(19991001)5:10<2921::aid-chem2921>3.0.co;2-1

文献信息

• Solvent induced cooperativity of Zn(<scp>ii</scp>) complexes cleaving a phosphatediester RNA analog in methanol
  作者：Mark F. Mohamed、Irma Sánchez-Lombardo、Alexei A. Neverov、R. Stan Brown

  DOI：10.1039/c1ob06482g

  日期：——

  The kinetics of cyclization of 2-hydroxypropyl p-nitrophenyl phosphate (1) promoted by two mononuclear Zn(II) catalytic complexes of bis(2-pyridylmethyl)benzylamine (4) and bis(2-methyl 6-pyridylmethyl)benzylamine (5) in methanol were studied under sspH-controlled conditions (where sspH refers to [H+] activity in methanol). Potentiometric titrations of the ligands in the absence and presence of Zn2+ and a non-reactive model for 1 (2-hydroxylpropyl isopropyl phosphate (HPIPP, 6)) indicate that the phosphate is bound tightly to the 4:Zn(II) and 5:Zn(II) complexes as L:Zn(II):6−, and that each of these undergoes an additional ionization to produce L:Zn(II):6−:(−OCH3) or a bound deprotonated form of the phosphate, L:Zn(II):62−. Kinetic studies as a function of [L:Zn(II)] indicate that the rate is linear in [L:Zn(II)] at concentrations well above those required for complete binding of the substrate. Plots of the second order rate constants (defined as the gradient of the rate constant vs. [complex] plot) vs.sspH in methanol are bell-shaped with rate maxima of 23 dm mol−1 s−1 and 146 dm mol−1 s−1 for 4:Zn(II) and 5:Zn(II), respectively, at their sspH maxima of 10.5 and 10. A mechanism is proposed that involves binding of one molecule of complex to the phosphate to yield a poorly reactive 1 : 1 complex, which associates with a second molecule of complex to produce a transient cooperative 2 : 1 complex within which the cyclization of 1 is rapid. The observations support an effect of the reduced polarity solvent that encourages the cooperative association of phosphate and two independent mononuclear complexes to give a reactive entity.

  在 sspH 控制条件下（其中 sspH 指甲醇中的 [H+] 活性），研究了双(2-吡啶基甲基)苄胺 (4) 和双(2-甲基-6-吡啶基甲基)苄胺 (5) 的两种单核 Zn(II) 催化配合物在甲醇中促进 2- 羟基丙基对硝基苯磷酸酯 (1) 环化的动力学。在没有和有 Zn2+ 以及 1 的非反应模型（2-羟基丙基异丙基磷酸酯（HPIPP，6））的情况下，配体的电位滴定表明，磷酸酯与 4：和 5:Zn(II) 复合物紧密结合，形成 L:Zn(II):6- 复合物，并且每种复合物都经过额外的电离作用，生成 L:Zn(II):6-:(-OCH3) 或磷酸的结合去质子化形式 L:Zn(II):62-。与[L:Zn(II)]函数相关的动力学研究表明，在[L:Zn(II)]浓度远高于底物完全结合所需的浓度时，速率与[L:Zn(II)]呈线性关系。甲醇中的二阶速率常数（定义为速率常数对[复合物]曲线图的梯度）对spH的曲线图呈钟形，4:Zn(II) 和 5:Zn(II) 的速率最大值分别为 23 dm mol-1 s-1 和 146 dm mol-1 s-1，它们的spH最大值分别为 10.5 和 10。提出的机理包括：一分子络合物与磷酸盐结合产生反应性差的 1 ：1 复合物，该复合物与第二分子复合物结合产生瞬时合作 2 ：1 复合物，在该复合物中，1 迅速环化。这些观察结果表明，极性降低的溶剂会促进磷酸盐和两个独立的单核络合物的合作结合，从而产生活性实体。
• Structure and dioxygen-reactivity of copper(i) complexes supported by bis(6-methylpyridin-2-ylmethyl)amine tridentate ligands
  作者：Takao Osako、Shohei Terada、Takehiko Tosha、Shigenori Nagatomo、Hideki Furutachi、Shuhei Fujinami、Teizo Kitagawa、Masatatsu Suzuki、Shinobu Itoh

  DOI：10.1039/b500202h

  日期：——

  intermediate was also altered by the supporting ligand. Namely, oxygenation of copper(I) complex 2R at a low temperature gave a (μ-η2:η2-peroxo)dicopper(II) complex as in the case of 1Phe, but its O–O bond was relatively weakened as compared to the peroxo complex derived from 1Phe, and a small amount of a bis(μ-oxo)dicopper(III) complex co-existed. These results can be attributed to the higher electron-donor

  的结构和铜的分子氧反应性（我）络合物2 - [R通过支持N，N-双（6-甲基吡啶-2-基甲基）胺 三齿的 配体研究了L2 R [R（N-烷基取代基）= –CH 2 Ph（Bn），– CH 2 CH 2 Ph（Phe）和–CH 2 CHPh 2 （PhePh）]，并与铜（I）进行了比较。的1 Phe的复数N，N-双[2-（吡啶-2-基）乙基]胺 三齿的 配体L1的Phe和铜（我）络合物3的Phe的N，N-双（吡啶-2-基甲基）胺 三齿的 配体L3苯丙氨酸。铜（我）络合物2的Phe和2 PhePh表现出涉及与广告η-π相互作用畸变三角金字塔结构1所述的金属离子和一个之间结合位模式邻-碳的原子苯基所述的Ñ -烷基取代基[-CH 2 CH 2 Ph（上苯丙氨酸）和-CH 2 CHPh配合2 （PhePh）]。在d-π相互作用的强度2的Phe和2 PhePh比用一个η的d-π相互作用的弱2在结合位模
• Coordination Alternatives in Dinuclear Bis(pyridin‐2‐ylalkyl)benzylaminecopper(II) Complexes with OH ^– , RO ^– , F ^– , or Cl ^– Bridges: Experimental Structures and DFT Preferences
  作者：Jorge Manzur、Andrés Vega、Ana María García、Carolina Acuña、Monika Sieger、Biprajit Sarkar、Mark Niemeyer、Falk Lissner、Thomas Schleid、Wolfgang Kaim

  DOI：10.1002/ejic.200700637

  日期：2007.12

  compounds [L 1 cu(μ-OH) 2 CuL 1 ](ClO 4 ) 2 (1), [L 2 Cu(μ-OH) 2 CuL 2 ](ClO 4 ) 2 (2), [L 3 Cu(μ-OH) 2 CuL 3 ](ClO 4 ) 2 (3), [L 3 Cu-(μ-OMe) 2 CuL 3 ](ClO 4 ) 2 (4), [L3Cu(μ-F)2CuL3](BF 4 ) 2 (5), [L 4 Cu-(μ-Cl) 2 CuL 4 ](ClO 4 ) 2 (6), and [Cu(μ-L 5 ) 2 Cu](ClO 4 ) 2 (7), where L 1 = bis(pyridin-2-ylmethyl)benzylamine, L 2 = (6-methylpyridin-2-ylmethyl)(pyridin-2-ylmethyl)benzylamine, L 3 = bis(6

  化合物[L 1 cu(μ-OH) 2 CuL 1 ](ClO 4 ) 2 (1), [L 2 Cu(μ-OH) 2 CuL 2 ](ClO 4 ) 2 (2), [L 3 Cu (μ-OH) 2 CuL 3 ](ClO 4 ) 2 (3), [L 3 Cu-(μ-OMe) 2 CuL 3 ](ClO 4 ) 2 (4), [L3Cu(μ-F)2CuL3] (BF 4 ) 2 (5)、[L 4 Cu-(μ-Cl) 2 CuL 4 ](ClO 4 ) 2 (6) 和[Cu(μ-L 5 ) 2 Cu](ClO 4 ) 2 ( 7)，其中L 1 = 双(吡啶-2-基甲基)苄胺，L 2 = (6-甲基吡啶-2-基甲基)(吡啶-2-基甲基)苄胺，L 3 = 双(6-甲基吡啶-2-基甲基) )苄胺，L 4 = (吡啶-2-基乙基)(吡啶-2-基甲基)苄胺，并且L 5 = (6-氧化甲基吡啶-2-基甲基)
• Open-Shell Organometallic [M^II(dbcot(bislutidylamine)]²⁺ Complexes (M = Rh, Ir): Unexpected Base-Assisted Reduction of the Metal Instead of Amine Ligand Deprotonation
  作者：Wojciech I. Dzik、Luis Fuente Arruga、Maxime A. Siegler、Anthony L. Spek、Joost N. H. Reek、Bas de Bruin

  DOI：10.1021/om101157r

  日期：2011.4.11

  Cationic rhodium and iridium complexes with dibenzo[a,e]cyclooctatetraene (dbcot) and bislutidylamine (bla) were synthesized from the respective [M(μ-Cl)(dbcot)]2 dimers and the bla ligand and were characterized by NMR, X-ray diffraction, and cyclic voltammetry. Both [MI(dbcot)(bla)]+ complexes are easily oxidized by one electron to form paramagnetic dicationic analogues [MII(dbcot)(bla)]2+ (M = Rh

  由各自的[M（μ-Cl）（dbcot）] 2个二聚体和bla配体合成了阳离子苯并铱和铱与二苯并[ a，e ]环辛酸酯（dbcot）和双戊二胺（bla）的配合物，并通过NMR，X表征射线衍射和循环伏安法。两种[M I（dbcot）（bla）] +络合物都容易被一个电子氧化，形成顺磁性的类似指示物[M II（dbcot）（bla）] 2+（M = Rh，Ir）。在固态下，当金属从M I氧化为M II时，几何形状从变形的三角双锥体转变为方形锥体，通过铱配合物的X射线衍射研究证明。在碱的存在下，顺磁性络合物容易进行单电子还原，这很可能涉及溶剂或氢氧根阴离子的氧化。使用相应的[Rh II（dbcot）（Bn-bla）] 2+配合物（其中Bn-bla是N-苄基保护的bla配体）进行的对照实验得出相似的结果，这强烈表明NH的去质子化[M II（dbcot）（bla）] 2+的部分在观察到的碱基介导的还原
• Cobalt Chloride Complexes of N ₃ and N ₄ Donor Ligands
  作者：T. Martijn Kooistra、Koen F. W. Hekking、Quinten Knijnenburg、Bas de Bruin、Peter H. M. Budzelaar、René de Gelder、Jan M. M. Smits、Anton W. Gal

  DOI：10.1002/ejic.200390090

  日期：2003.2

  AbstractA number of cobalt(II) chloride complexes of pyridine/amine N3 and N4 donors have been prepared and structurally characterised. Even though they are paramagnetic, assignment of the 1H NMR signals was possible in several cases. With the exception of tpa, which formed a cationic monochloride complex, all new complexes have cis‐coordinated chlorides. Nevertheless, only the relatively rigid pyp ligands gave rise to (low) ethene polymerisation activity on activation with MAO. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)