tris[2-(((5-methylimidazol-4-yl)methylidene)amino)ethyl]amine | 680586-44-1

• 英文名称: tris[2-(((5-methylimidazol-4-yl)methylidene)amino)ethyl]amine
• 英文别名: tris{2-[(4-methylimidazol-5-yl)methylideneamino]ethyl}amine；tren(4-Me-5-ImH)3；2-[(5-methyl-1H-imidazol-4-yl)methylideneamino]-N,N-bis[2-[(5-methyl-1H-imidazol-4-yl)methylideneamino]ethyl]ethanamine
• CAS: 680586-44-1
• 化学式: C₂₁H₃₀N₁₀
• 分子量: 422.536
• InChiKey: SRQGNOAYTVTKOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

   tris[2-(((5-methylimidazol-4-yl)methylidene)amino)ethyl]amine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 N-[(5-methyl-1H-imidazol-4-yl)methyl]-N',N'-bis[2-[(5-methyl-1H-imidazol-4-yl)methylamino]ethyl]ethane-1,2-diamine
  参考文献：
  名称：

  Correlation of nitrogen chirality, R or S, with metal chelate chirality, Δ or Λ, in a series of reduced tripodal Schiff base complexes. A route to total spontaneous resolution

  摘要：

  Tripodal Schiff base ligands, L-ox, were prepared in situ by the 3:1 condensation of 5-methyl-4-imidazole carboxaldehyde, 2-imidazole carboxaldehyde or 1-methyl-2-imidazole carboxaldehyde with tris(2-aminoethyl) amine, tren. The Schiff base ligands were reduced in situ by established procedures with sodium borohydride to give the amine form of the ligand, L-red. Complexes of manganese(II) or iron(II), [MLred] X-2 (X = ClO4-, BF4- or PF6-) were prepared and characterized by IR, ESI MS, single crystal X-ray diffraction and Mossbauer spectroscopy for the iron(II) complex. The structures of the complexes are best described as mono capped trigonal antiprismatic with the center nitrogen atom of the tren capping the amine face. In all cases the three amine nitrogen atoms of the tripodal ligand are homochiral (RRR or SSS) within the same complex. Further, in the eight complexes examined the chirality of the nitrogen atom correlates with the metal chelate chirality. Specifically R correlates with K, and S correlates with D. Simple molecular mechanics calculations are consistent with this experimental observation. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.10.027
• 作为产物：
  描述：

  三(2-氨基乙基)胺 、 5-甲基咪唑-4-甲醛 以 甲醇 为溶剂， 反应 1.0h， 以80%的产率得到 tris[2-(((5-methylimidazol-4-yl)methylidene)amino)ethyl]amine
  参考文献：
  名称：

  包含三个咪唑臂的三脚架席夫碱配体的新的二和三有机锡（IV）配合物：合成，结构表征，抗炎活性和热学研究

  摘要：

  一些新的三-和二有机锡（IV）通式中，R的配合物3的Sn（H 2 L）和R' 2的Sn（HL）[其中R = Me中，Ñ -Pr，Ñ -Bu且Ph; R′＝ Me，n- Bu，Ph和n- Oct；H 3 L =席夫碱（缩写为tren（4-Me-5-ImH）3），由三（2-氨基乙基）胺（tren）和4-甲基-5-咪唑甲醛（4-Me-5-5）缩合衍生而来ImH）]已经合成。基于红外和远红外，119 SnMössbauer和多核（1 H，13 C和119Sn）磁共振（NMR）光谱研究。已经使用TG，DTG和DTA技术对所有合成的有机锡（IV）配合物进行了热研究。通过X-射线粉末衍射分析和IR表征了从研究的复合物的热解中获得的残留物。已对新合成的复合物的抗炎活性和毒性进行了测试（LD 50）。

  DOI：

  10.1016/j.jorganchem.2010.02.009

文献信息

• Enantioselective aggregation and luminescence properties of europium(III) and terbium(III) complexes of an acetate and a tripodal ligand containing three imidazole groups
  作者：Mami Murase、Suguru Yamauchi、Soichiro Sakamoto、Saori Takahashi、Naohide Matsumoto、Masanobu Tsuchimoto

  DOI：10.1016/j.poly.2013.04.040

  日期：2013.8

  mino)ethyl]amine, and OAc = acetate ion. Each EuIII or TbIII ion is coordinated by a heptadentate tripodal and a bidentate acetate ligand, resulting in Δ- and Λ-enantiomorphs because of the screw coordination arrangement of the tripodal ligand. Intermolecular imidazole⋯acetate hydrogen bonding gives rise to three types of enantioselective assemblies. Compounds 1 and 4 form homochiral 1D chains comprising

  3双铕的聚集和发光性能III（1 - 3）和同晶Tb的III（4 - 6复合物连接到三角架heptadentate N）7的配体和二齿乙酸根离子，[Eu的III或Tb III（H 3大号2-我）（OAC）]（CLO 4）2 ·2MeOH·H 2 O（1，  4），[Eu的III或Tb III（H 3大号2-ME）（OAC）]（CLO 4）2·2EtOH（2，  5），和[Eu的III或Tb III（H 3大号5-ME）（OAC）]（CLO 4）2 ·甲醇（3，  6），进行了研究，其中H 3大号2-ME  =三[2-（（（（2-甲基咪唑-4-基）亚甲基）氨基）乙基]胺和H 3 L 5-Me  =三[2-（（（5-甲基咪唑-4-基）亚甲基）氨基）乙]胺，OAc =乙酸根离子。每个Eu III或Tb III离子由七足的三脚架和乙酸二齿配体配位，由于三脚架配体的螺丝配位结构，导致Δ-和Λ对映体。
• Homo- and Heterochiral Aggregations of Samarium(III) Complexes with Acetate and Tripod Ligand Containing Three Imidazole Groups
  作者：Saori Takahashi、Mami Murase、Hiroaki Hagiwara、Naohide Matsumoto、Masanobu Tsuchimoto

  DOI：10.1246/bcsj.20110141

  日期：2011.10.15

  Three SmIII complexes with tripod heptadentate N7 ligands containing three imidazole groups, [Sm(H3L2-Me)(ac)](ClO4)2·2MeOH·H2O (1), [Sm(H3L2-Me)(ac)](ClO4)2·2EtOH (2), and [Sm(H3L4-Me)(ac)](ClO4)2·MeOH (3), were synthesized and the crystal structures were determined, where H3L2-Me and H3L4-Me are the 1:3 condensation products of tris(2-aminoethyl)amine and either 2-methyl-4-formylimidazole and 4-methyl-5-formylimidazole, respectively, and ac denotes acetate ion. Each SmIII ion is coordinated by a tripod heptadentate N7 ligand and two oxygen atoms of the acetate ion. Due to the screw coordination arrangement of the achiral tripod ligand to the SmIII ion, the complex-cation [SmIII(H3L2- or 4-Me)(ac)]2+ gives Δ- and Λ-enantiomorphs. In compounds 1 and 2, two adjacent [Sm(H3L2-Me)(ac)]2+ species with the same chirality are linked by an intermolecular imidazole···acetate hydrogen bond to form a homochiral 1D chain structure. Adjacent chains with the same chirality are stacked to give a conglomerate crystal in 1, while adjacent chains with opposite chiralities are stacked to give a racemic crystal in 2. In compound 3, two adjacent [Sm(H3L4-Me)(ac)]2+ species with the opposite chiralities are doubly bridged by two intermolecular imidazole···acetate hydrogen bonds to form a heterochiral dimer and the adjacent dimers are connected by ClO4− ion through the hydrogen bonds to form a racemic crystal.

  合成了含有三个咪唑基团的三足七价 N7 配体的 SmIII 复合物，即 [Sm(H3L2-Me)(ac)](ClO4)2-2MeOH-H2O (1)、[Sm(H3L2-Me)(ac)]( )2-2EtOH (2)和 [Sm(H3L4-Me)(ac)]( )2-MeOH (3)、合成了[Sm(H3L4-Me)(ac)]( )2-MeOH (3)，并测定了它们的晶体结构，其中 H3L2-Me 和 H3L4-Me 是 1：其中，H3L2-Me 和 H3L4-Me 分别是三(2-氨基乙基)胺与 2-甲基-4-甲酰基咪唑和 4-甲基-5-甲酰基咪唑的 1：3 缩合产物，ac 表示乙酸根离子。每个 SmIII 离子都由三脚七齿 N7 配体和乙酸根离子的两个氧原子配位。由于非手性三脚配体与 SmIII 离子的螺旋配位排列，络合物阳离子 [SmIII(H3L2- 或 4-Me)(ac)]2+会产生 Δ- 和Λ-非对映异构体。在化合物 1 和 2 中，两个具有相同手性的相邻[Sm(H3L2-Me)(ac)]2+ 物种通过分子间咪唑--乙酸酯氢键相连，形成了同手性的一维链结构。在化合物 3 中，两个相邻的具有相反手性的[Sm(H3L4-Me)(ac)]2+物种通过两个分子间咪唑----乙酸酯氢键双桥连成异手性二聚体，相邻的二聚体通过 - 离子氢键连接成外消旋晶体。