N'-(pyridin-2-ylmethyl)-N,N-bis{2-[(pyridin-2-ylmethyl)amino]ethyl}ethane-1,2-diamine | 122329-11-7

• 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-2-ylmethyl)-N,N-bis{2-[(pyridin-2-ylmethyl)amino]ethyl}ethane-1,2-diamine
• 英文别名: tris[N-(2-pyridylmethylene)-2-aminoethyl]amine；tris[2-[N-(2-pyridinemethyl)amino]ethyl]amine；tris-(2-((2-pyridylmethyl)amino)ethyl)amine；tris[2[N-(2-pyridylmethyl)amino]ethyl]amine；tris[N-(2-pyridylmethyl)-2-aminoethyl]amine；tris(2-((2-pyridylmethyl)amino)ethyl)amine；Tris[2-{(2-pyridylmethyl)amino}ethyl]amine；N-(pyridin-2-ylmethyl)-N',N'-bis[2-(pyridin-2-ylmethylamino)ethyl]ethane-1,2-diamine
• CAS: 122329-11-7
• 化学式: C₂₄H₃₃N₇
• 分子量: 419.573
• InChiKey: SDWXTQCFTPNNKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N'-(pyridin-2-ylmethyl)-N,N-bis{2-[(pyridin-2-ylmethyl)amino]ethyl}ethane-1,2-diamine 在 双(二甲基氨)氯膦 作用下， 以 四氢呋喃 为溶剂， 以61.9%的产率得到
  参考文献：
  名称：

  Flexibility is Key: Synthesis of a Tripyridylamine (TPA) Congener with a Phosphorus Apical Donor and Coordination to Cobalt(II)

  摘要：

  Tripyridylamine (TPA), a tetradentate ligand that forms 5-membered chelate rings upon metal coordination, has demonstrated significant utility in synthetic inorganic chemistry. An analogue with a phosphorus apical donor is a desirable target for tuning electronic structure and enhancing reactivity. However, this congener has been synthetically elusive. Prior attempts have resulted in tridentate coordination to transition metal ions due to a lack of ligand flexibility. Herein, we report the successful synthesis of tris(2-pyridylmethyl)proazaphosphatrane (TPAP), a more accommodating tripyridyl ligand containing an apical phosphorus donor. The TPAP ligand forms 6-membered chelate rings upon coordination and binds in the desired tetradentate fashion to a Co(II) ion. Structural studies elucidate the importance of ligand flexibility in tripodal ligands featuring phosphorus donors. Cyclic voltammetry, UV-vis, and solution magnetic susceptibility experiments of [Co(TPAP)(CH3CN)](2+) are also reported and compared to [Co(TPA)(CH3CN)](2+). Notably, magnetic susceptibility measurements of [Co(TPAP)(CH3CN)](2+) indicate a low spin electronic configuration, in contrast to [Co(TPA)(CH3CN)](2+), which is high spin.

  DOI：

  10.1021/acs.inorgchem.5b02133
• 作为产物：
  描述：

  三(2-氨基乙基)胺 在 sodium tetrahydroborate 作用下， 以 甲醇 、 苯 为溶剂， 反应 36.0h， 生成 N'-(pyridin-2-ylmethyl)-N,N-bis{2-[(pyridin-2-ylmethyl)amino]ethyl}ethane-1,2-diamine
  参考文献：
  名称：

  Evaluation of copper chelation agents as anti-angiogenic therapy

  摘要：

  The design, synthesis and evaluation of N,N',N"-tris(2-pyridylmethyl)-cis,cis-1,3,5,-triaminocyclohexane (tachpyr, 1) derivatives as novel anti-angiogenic agents were performed in an in vitro endothelial cell proliferation assay to assess their cytotoxicity and selectivity. The selective nature of the anti-angiogenic agents for human umbilical vein endothelial cells (HUvec) was compared to a normal fibroblast cell line and a human Glioma cell line to evaluate these compounds. N,N',N"-tris(2-mercaptoethyl)-cis,cis-1,3,5-triaminocyclohexane trihydrochloride (3b) was superior to tachpyr in terms of selectivity of its inhibitory activity toward the proliferation of Huvec compared to the fibroblast and human Glioma cell lines. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00401-2

文献信息

• Gas, solution, and solid state coordination environments for the nickel(II) complexes of a series of aminopyridine ligands of varying coordination number
  作者：JudithAnn R Hartman、Richard W Vachet、John H Callahan

  DOI：10.1016/s0020-1693(99)00288-1

  日期：2000.1

  binding geometries of the nickel(II) complexes in the solid, solution, and gas phases: magnetic susceptibility measurements, absorption spectroscopy, electrochemistry, and analyzing the gas phase ion-molecule reactions in a mass spectrometer. The linked five-membered chelate character of the linear ligands appear to have imposed high-spin, octahedral geometry on the complexes in the condensed phases. The

  摘要描述了一系列氨基吡啶配体从三齿到七齿的镍（II）配合物的合成和表征。配体包括三脚架配体三（2-（（2-吡啶基甲基）氨基）乙基）胺，TREN-pyr和以下线性配体：（2-吡啶基甲基）（2-（2-（（2-（（2 -吡啶基甲基）氨基）乙基）氨基）乙基）胺，TRIEN-pyr;双（2-（（（2-吡啶基甲基）氨基）乙基）胺，DIEN-pyr;（2-吡啶基甲基）（2-（（2-吡啶基甲基） ）氨基）乙基）胺，EN-pyr;双（2-吡啶基甲基）胺，AM-pyr;和甲基（2-（（（吡啶基甲基）氨基）乙基）胺，MeEN-pyr。采用以下方法测定固相，溶液和气相中镍（II）配合物的结合几何形状：磁化率测量，吸收光谱，电化学，在质谱仪中分析气相离子分子反应。线性配体的连接的五元螯合特征似乎在凝聚相中对复合物施加了高自旋八面体的几何形状。三脚架配体TREN-pyr和两个三齿配体AM-pyr和MeEN-pyr在气
• A comparison of the gas, solution, and solid state coordination environments for the copper(II) complexes of a series of aminopyridine ligands of varying coordination number
  作者：JudithAnn R Hartman、Richard W Vachet、Wayne Pearson、R.Jeremy Wheat、John H Callahan

  DOI：10.1016/s0020-1693(02)01229-x

  日期：2003.1

  copper(II) complexes of a series of aminopyridine ligands that range from tri- to heptadentate is described. The ligands include the tripod ligand tris(2-((2-pyridylmethyl)amino)ethyl)amine, TREN-pyr, and the following linear ligands: (2-pyridylmethyl)(2-(2-(2-((2-pyridylmethyl)amino)ethyl)amino)ethyl)amine, TRIEN-pyr; bis(2-((2-pyridylmethyl)amino)ethyl)amine, DIEN-pyr; (2-pyridylmethyl)(2-((2-pyr

  摘要描述了范围从三齿到七齿的一系列氨基吡啶配体的铜（II）配合物的合成和表征。配体包括三脚架配体三（2-（（（2-吡啶基甲基）氨基）乙基）胺，TREN-pyr和以下线性配体：（2-吡啶基甲基）（2-（2-（2-（（2-吡啶基甲基）氨基）乙基）氨基）乙基）胺，TRIEN-pyr；双（2-（（（2-吡啶基甲基）氨基）乙基）胺，DIEN-pyr; （2-吡啶基甲基）（2-（（（2-吡啶基甲基）氨基）乙基）胺，EN-pyr; 双（2-吡啶基甲基）胺，AM-pyr; 和甲基（2-（（-（吡啶基甲基）氨基）乙基）胺，MeEN-pyr。以下方法用于确定固相，溶液和气相中Cu（II）配合物的结合几何形状：磁化率测量，吸收光谱，EPR光谱，电化学，在质谱仪中分析气相离子分子反应。通过X射线晶体学测定TRIEN-pyr和DIEN-pyr复合物的固态结构。[Cu（TRIEN-pyr）]（BF 4）2在八面体系统空间群Pbca中结晶，其a
• A Seven-Coordinate Manganese(II) Complex Formed with a Single Tripodal Heptadentate Ligand as a New Superoxide Scavenger
  作者：Alain Deroche、Irène Morgenstern-Badarau、Michèle Cesario、Jean Guilhem、Bineta Keita、Louis Nadjo、Chantal Houée-Levin

  DOI：10.1021/ja952508l

  日期：1996.1.1

  A new manganese(II) complex, Mn(II)−tris[2-[N-(2-pyridylmethyl)amino]ethyl]bishexafluorophosphate (Mn−TPAA), has been synthesized, its X-ray crystal structure resolved, and its superoxide stoichiometric scavenging activity established. The complex has been formed with the tripodal potentially heptadentate ligand TPAA which turns out to be the single ligand coordinated to the metal ion and therefore

  合成了一种新的锰 (II) 配合物 Mn(II)-三[2-[N-(2-吡啶基甲基)氨基]乙基]双六氟磷酸酯 (Mn-TPAA)，其 X 射线晶体结构得到解析，并且建立了超氧化物化学计量清除活性。该配合物已与三足潜在七齿配体 TPAA 形成，TPAA 是与金属离子配位的单一配体，因此实现了七配位。该配合物在空间群 P212121 中结晶，a = 19.654(9) A，b = 15.416(5) A，c = 10.425(4) A，每个晶胞有四个分子式单元。锰与三个吡啶氮原子、三个胺基团和三足桥氮 N 键合。 已使用间接黄嘌呤 - 黄嘌呤氧化酶 - 细胞色素 c 方法研究了对超氧化物的反应性，原位产生超氧化物的电化学反应，以及γ和脉冲辐解测量。从细胞色素 c 试验中发现，IC50 值等于 4.4 μM。从电...
• Amine conformational change and spin conversion induced by metal-assisted ligand oxidation: from the seven-coordinate iron(II)–TPAA complex to the two oxidized iron(II)–(py)3tren isomers. Characterization, crystal structures, and density functional study
  作者：Irène Morgenstern-Badarau、François Lambert、Jean Philippe Renault、Michèle Cesario、Jean-Didier Maréchal、Feliu Maseras

  DOI：10.1016/s0020-1693(99)00363-1

  日期：2000.1

  between complexes 2 and 3 with a pseudo-coordination of six as shown by the N tripodal Fe distance equal to 2.754 A. Electronic changes were recognized from NMR studies in solution and EPR and SQUID measurements of susceptibilities in solid state. Complex 1 is high-spin with the S =2 state characterized by a g factor equal to 2.25. Complex 3 is low-spin but its isomer, the intermediate complex 2 exhibits

  摘要发现三脚架七齿配体TPAA（TPAA = tris [N-（2-吡啶基甲基）-2-氨基乙基]胺）受到铁（II）辅助的氧化脱氢，其三个胺官能团被氧化为三个亚胺基，得到三脚架潜在的七齿配体（py）3 tren（（py）3 tren =三[N-（2-吡啶基甲基）-2-亚氨基乙基]胺）。该氧化过程诱导了三种已鉴定的铁（II）配合物Fe–TPAA配合物（1），Fe–py3tren配合物（2）和（3）的结构变化和自旋转化。X射线晶体学研究表明，桥接氮原子的配位几何结构不同，配位数从7变到6。配合物1是七坐标的，其特征是三脚架中心的氮呈锥体环境，且N的短三脚架Fe距离等于2。配合物504A。配合物3是六坐标的，中心氮的平面环境位于距铁（II）3.435 A的位置，因此不与铁结合。配合物2是配合物3的异构体形式，发现它是配合物2和3之间的结构中间物，假配位为6，如N三脚架Fe距离等于2.754 A
• Encapsulating ruthenium and osmium with tris(2-aminoethyl)amine based tripodal ligands
  作者：Soumik Mandal、Dipravath K. Seth、Parna Gupta

  DOI：10.1016/j.poly.2011.09.010

  日期：2012.1

  The reaction of a series of tripodal ligands, H3L1.2 and L3-6, with [M(PPh3)(2)Cl-2[(M = Ru, Os) affords a family of coordination cage compounds of the type [(ML1.2)-L-III] (1-4) or [(ML3-6)-L-II](BPh4)(2) (5-12). The Schiff base ligands (H3L1, L-3, L-5) have been synthesized by condensation of tris(2-aminoethyl)amine with salicylaldehyde, pyridine-2-aldehyde and 1-methy1-2-imidazolecarboxaldehyde. These ligands were further reduced and subsequently methylated to form the new ligands (H3L2, L-4, L-6). Single crystal X-ray diffraction studies of 1 and 2 show that the tripodal ligand wraps around the metal center as a hexadentate ligand to form a cage. All the synthesized compounds have been thoroughly characterized by ESI-MS, FT-IR, UV-Vis and NMR spectroscopic methods. To the best of our knowledge, this is the first ever report of osmium complexes with tris(2-aminoethyl)amine based tripodal ligands. DFT calculations were performed to obtain geometry optimized structures of all the other complexes (3-12). (C) 2011 Elsevier Ltd. All rights reserved.