N,N-bis(2-ethyl-5-methylimidazol-4-ylmethyl)aminopropane | 291506-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N,N-bis(2-ethyl-5-methylimidazol-4-ylmethyl)aminopropane
• 英文别名: N,N-bis(2-ethyl-5-methyl-imidazolyl-4-methyl)aminopropane；N,N-bis[(2-ethyl-5-methyl-1H-imidazol-4-yl)methyl]propan-1-amine
• CAS: 291506-28-0
• 化学式: C₁₇H₂₉N₅
• 分子量: 303.451
• InChiKey: VJDUXSKMZNYGAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  60.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tetrakis(actonitrile)copper(I) hexafluorophosphate 、 N,N-bis(2-ethyl-5-methylimidazol-4-ylmethyl)aminopropane 在 HBF₄ 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 [(N,N-bis(2-ethyl-5-methyl-imidazol-4-yl-methyl)-aminopropane)copper(I)]PF6
  参考文献：
  名称：

  Copper complexes of a new tridentate imidazole-containing ligand: spectroscopy, structures and nitrite reductase reactivity

  摘要：

  The ligand N,N-bis(2-ethyl-5-methyl-imidazol-4-ylmethyl)-aminopropane (abbreviated as biap) forms several copper(II) coordination compounds with general formula [Cu(biap)X-2], with X- = Cl-, Br-,NO3-, NO2- and NCS-. In all these compounds the ligand biap acts as a tridentate ligand. Single crystals of [Cu(biap)(NO2)(2)] and [Cu(biap)Br-2] were used for X-ray structure determinations. All compounds were characterized by IR, ligand field and EPR spectroscopy, and cyclic voltammetry. The geometry of copper(EI) in the (pseudo-) halide complexes is five coordinate, whereas copper(II) is distorted octahedrally coordinated in the nitrate and nitrite complexes, whereby one of the anions binds didentate chelating and the other one monodentate. The affinity of nitrite for the [Cu(biap)](2+) cation was studied by determining the binding constant of the anion to the perchlorate salt of the complex in methanol solution. The data show that nitrite exhibits high affinity for the complex and its behavior is comparable with that of azide. The reduction of nitrite, to produce nitric oxide, by the reduced complex [Cu(biap)](+) has been studied anaerobically. Kinetic experiments showed that the reaction exhibits saturation behavior with respect to nitrite concentration. The kinetic data indicate that [Cu(biap)](+) has a moderate efficiency in the nitrite reductase reaction. (C) 2000 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0020-1693(00)00271-1
• 作为产物：
  描述：

  正丙胺 、 聚合甲醛 、 2-乙基-4-甲基咪唑 在 potassium hydroxide 作用下， 以 水 为溶剂， 生成 N,N-bis(2-ethyl-5-methylimidazol-4-ylmethyl)aminopropane
  参考文献：
  名称：

  咪唑和螯合环尺寸在铜氧化催化剂中的作用：实验和理论研究

  摘要：

  在这项工作中，研究了咪唑和吡啶配体配合物的结构、溶液、电化学和催化性能。提出了五种具有或不具有配位咪唑和不同螯合环尺寸的仿生铜催化剂的比较研究。通过 Michaelis-Menten 模型评估了MeOH/H 2 O 介质中3,5-二叔丁基儿茶酚 (DTBC) 和邻氨基苯酚 (OAP) 氧化的催化效率。包含含咪唑配体和/或六元螯合环的催化剂被证明在两种氧化反应中都更有效。铜配合物的稳定性常数和电化学参数的测定支持了催化行为的解释。已经提出了两种反应类似的催化循环。所有五种配合物和两种催化反应的密度泛函理论（DFT）自由能计算结果与实验结果一致。

  DOI：

  10.1021/acs.inorgchem.3c01236

文献信息

• Tuning the coordination mode in mononuclear manganese complexes by changing the steric bulk of the carboxylates
  作者：Sabine T. Warzeska、Fabrizio Miccichè、M. Chiara Mimmi、Elisabeth Bouwman、Huub Kooijman、Anthony L. Spek、Jan Reedijk

  DOI：10.1039/b104975p

  日期：2001.12.3

  Three mononuclear manganese complexes of the tridentate ligand biap [ = N,N-bis(2-ethyl-5-methylimidazol-4-ylmethyl)aminopropane] with various carboxylates as co-ligands have been synthesized and structurally characterised by X-ray diffraction. All three complexes can be described by the general formula [MnII(biap)(RCOO)2(H2O)n] (n = 0, 1). The manganese(II) ion in [MnII(biap)(C6H5COO)2] (1) is five coordinated by three nitrogen donors from biap and two oxygen donors of monodentate benzoate molecules. This monodentate binding mode is confirmed by IR analysis. In the compound [MnII(biap)((C6H5)2CHCOO)2(H2O)] (2), the manganese ion is coordinated in a distorted octahedron with an additional water molecule as the sixth ligand. This aqua ligand forms strong intramolecular hydrogen bonds to both carboxylate groups as is reflected in the IR. Finally the manganese ion in the complex [MnII(biap)((C6H5)3CCH2COO)2] (3) is again five coordinated with triphenylpropionate as coordinating counter ion. In 3 both carboxylates are bound monodentately, but one shows a semi coordination of the free oxygen to the manganese center (Mn–O = 3.169 Å). Both carboxylates are involved in hydrogen bonding albeit to a different degree. This asymmetric binding mode is reflected in the IR spectrum, which shows two pairs of carboxylate vibrations. The structural differences of the three complexes are expressed by the very different X-band EPR spectra of the solid compounds. In solution, however, all three complexes are most likely octahedrally coordinated as indicated by their similar EPR spectra in frozen MeOH–EtOH solution.

  三种单核锰配合物，采用三齿配体biap [=N,N-bis(2-ethyl-5-methylimidazol-4-ylmethyl)aminopropane]，与各种羧酸盐作为共配体合成，并通过X射线衍射进行结构表征。这三种配合物的通用化学式为[MnII(biap)(RCOO)2(H2O)n]（n = 0, 1）。在配合物[MnII(biap)( COO)2] (1)中，锰(II)离子通过来自biap的三个氮捐赠原子和两个来自单牙苯酸分子的氧捐赠原子形成五配位。通过红外分析证实了这种单牙配位模式。在化合物[MnII(biap)((C6H5)2CHCOO)2( )] (2)中，锰离子以扭曲的八面体结构配位，并且额外的水分子作为第六配体。这种水合配体与两个羧酸盐基团形成强的分子内氢键，反映在红外光谱中。最后，在配合物[MnII(biap)(( )3CCH2COO)2] (3)中，锰离子再次以五配位方式与三苯基丙酸盐作为配位离子。在3中，两个羧酸盐均以单牙形式结合，但其中一个展示出自由氧与锰中心的半配位（Mn–O = 3.169 Å）。两个羧酸盐都参与氢键形成，尽管程度不同。这种不对称的配位模式在红外光谱中得以反映，显示出两对羧酸盐的振动。三种配合物的结构差异通过固体化合物的X波段EPR光谱的显著不同得以体现。然而在溶液中，所有三种配合物最可能以八面体配位的形式存在，正如其在冻干MeOH–EtOH溶液中相似的EPR光谱所示。
• Co(II), Ni(II), and Zn(II) compounds of the new tridentate ligand N,N-bis(2-ethyl-5-methyl-imidazol-4-ylmethyl)aminopropane (biap). X-ray structures of biap·H2O, [Co(biap)(NCS)(OAc)], [Ni(biap)(NCS)(OAc)], [Ni(biap)(NCS)2(MeCN)](MeCN), and [Ni(biap)2](BF4)2(EtOH)
  作者：Elisabeth Bouwman、Bénédicte Douziech、Lucia Gutierrez-Soto、Michela Beretta、Willem L Driessen、Jan Reedijk、Guillermo Mendoza-Dı́az

  DOI：10.1016/s0020-1693(00)00097-9

  日期：2000.6

  metal coordination compounds with the novel tridentate ligand N , N -bis(2-ethyl-5-methyl-imidazol-4-ylmethyl)-aminopropane (biap). Compounds with formulae [M(biap)(X)(Y)(H 2 O) n ]·(solvent) with X − , Y − =Cl − , Br − , NO 3 − , CH 3 COO − and NCS − , and n =0 or 1, and [M(biap) 2 ](BF 4 ) 2 ·(solvent), with M=Co 2+ , Ni 2+ , and Zn 2+ , as well as the dinuclear complexes [Ni(biap)X 2 ] 2 (X − =Cl

  摘要描述了18种具有新型三齿配体N，N-双（2-乙基-5-甲基-咪唑-4-基甲基）-氨基丙烷（biap）的过渡金属配位化合物的合成和表征。具有X-，Y-= Cl-，Br-，NO 3-，CH 3 COO-和NCS-的式[M（biap）（X）（Y）（H 2 O）n]·（溶剂）的化合物n = 0或1，以及[M（biap）2]（BF 4）2·（溶剂），其中M = Co 2+，Ni 2+和Zn 2+以及双核配合物[Ni（ biap）X 2] 2（X-＝ Cl-，NCS-）已被分离。除钴化合物[Co（biap）（NCS）（OAc）]（其中X射线结构表明胺氮键较弱）外，配体biap在子午面或面所有化合物中均作为三齿配体。几乎只有半配位（CoN= 2.387（4）A）。配体双键 通过一个非常简单的一锅一步缩合反应合成，然后与一分子水结晶。biap·H 2O。其单晶X射线结构揭示了基于氢键的三维网络，其中
• Corroborative cobalt and zinc model compounds of α-amino-β-carboxymuconic-ε-semialdehyde decarboxylase (ACMSD)
  作者：Jessica Gätjens、Christopher S. Mullins、Jeff W. Kampf、Pierre Thuéry、Vincent L. Pecoraro

  DOI：10.1039/b809453e

  日期：——

  We have synthesised and characterised a series of new CoII complexes (1–4, 6, 7) and one new ZnII complex (5) employing N3- and N3O-donor ligands [biap: N,N-bis(2-ethyl-5-methyl-imidazol-4-ylmethyl)amino-propane, KBPZG: potassium N,N-bis(3,5-dimethylpyrazolylmethyl) glycinate, KBPZA: potassium N,N-bis(3,5-dimethylpyrazolylmethyl) alaninate, KBiPrPZG: potassium N,N-bis(3,5-di-iso-propylpyrazolylmethyl) glycinate, and KB(tBuM)PZG: potassium N,N-bis(3-methyl-5-tert-butyl-pyrazolylmethyl)glycinate] as structural models of the metalloenzyme α-amino-β-carboxymuconic-ε-semialdehyde decarboxylase (ACMSD). These complexes were characterised by several techniques including X-ray crystallographic analysis, X-band EPR, and mass spectrometry (ESI-MS). The crystal structures of 1, 2, 6, 7 revealed that they exist as mononuclear Co(II) complexes with trigonal-bipyramidal geometry in the solid state. Compounds 3 and 5 form infinite polymeric chains of CoII or ZnII complexes, respectively, linked by the pendant carboxylate arms of the BPZG− ligand. By comparing the degree of distortion in the penta-coordinate complexes, defined by the Addison-parameter τ, with the value determined for the five-coordinate centres found in the active site of ACMSD, it could be seen that complexes 5 and 7 are very good matches for the geometry of the zinc(II) centre in monomer A of the native enzyme. All complexes could be seen as model compounds for the active site of the enzyme ACMSD, where the Co(II) complexes reflected the structural flexibility found in case of two histidine (His177 and His228) residues found in the active site of the enzyme.

  我们合成并表征了一系列新的CoII配合物（1–4，6，7）和一个新的ZnII配合物（5），采用了N3和N3O供体配体 [biap：N,N-bis(2-ethyl-5-methyl-imidazol-4-ylmethyl)amino-propane，KBPZG：钾N,N-bis(3,5-dimethylpyrazolylmethyl)甘氨酸，KBPZA：钾N,N-bis(3,5-dimethylpyrazolylmethyl)丙氨酸，KBiPrPZG：钾N,N-bis(3,5-di-iso-propylpyrazolylmethyl)甘氨酸，以及KB(tBuM)PZG：钾N,N-bis(3-methyl-5-tert-butyl-pyrazolylmethyl)甘氨酸]，作为酶α-氨基-β-羧基美克酮-ε-半醛脱羧酶（ACMSD）的结构模型。这些配合物通过包括X射线晶体学分析、X波段电子顺磁共振（EPR）和质谱（ESI-MS）等多种技术进行了表征。1、2、6、7的晶体结构表明，它们在固态下作为单核Co(II)配合物存在，具有三角双锥几何结构。化合物3和5分别形成无限的聚合链，这些链由BPZG配体的挂链羧酸臂连接的CoII或ZnII配合物所组成。通过比较五配位配合物中扭曲程度（以Addison-参数τ定义），与在ACMSD活性位点中发现的五配位中心的值进行对比，可以看出配合物5和7与天然酶单体A中锌（II）中心的几何形状非常吻合。所有配合物都可以视为酶ACMSD活性位点的模型化合物，其中Co(II)配合物反映了在酶活性位点发现的两种组氨酸（His177和His228）残基所体现的结构灵活性。
• Drier for air-drying coatings
  申请人：Oostveen Arnoldus Everardus

  公开号：US20050245639A1

  公开（公告）日：2005-11-03

  The invention pertains to a drier composition for air-drying alkyd-based coatings, inks, or floor coverings, comprising a combination of the following components: a) a transition metal salt with the formula: (Me n+ )(X k− ) m in which Me is the transition metal; X − represents a coordinating ligand; and k− is the valence state of the transition metal and m is the number of ligands X. b) a reducing biomolecule. The reducing biomolecule is in particular ascorbic acid or a derivative thereof, including ascorbyl palmitate.

  本发明涉及一种用于风干醇酸树脂涂料、油墨或地板覆盖物的干燥剂组合物，该组合物由以下成分组合而成：a) 一种过渡金属盐，其式为(Me n+ )(X k- ) m 其中 Me 为过渡金属；X - 代表配位配体；k- 是过渡金属的价态，m 是配体 X 的数目。还原性生物分子尤其是抗坏血酸或其衍生物，包括抗坏血酸棕榈酸酯。
• Copper(II) compounds of some Mannich-condensation amine–bis-imidazole ligands
  作者：Willem L Driessen、Daniëlle Rehorst、Jan Reedijk、Ilpo Mutikainen、Urho Turpeinen

  DOI：10.1016/s0020-1693(03)00224-x

  日期：2003.11

  The Mannich condensation of formaldehyde with some amines and imidazoles rendered four bis-imidazole ligands in a very simple one pot reaction. The X-ray structures of four copper(II) compounds, obtained with these ligands, show in all cases the copper(II) ions to be in a square pyramidal environment. Three compounds appeared to be mononuclear, while the least bulky ligand rendered a dinuclear complex. (C) 2003 Elsevier B.V. All rights reserved.