N,N′-bis(3-formyl-5-chlorosalicylidene)ethylenediimine | 167103-32-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N′-bis(3-formyl-5-chlorosalicylidene)ethylenediimine
• 英文别名: 5-Chloro-3-[2-[(5-chloro-3-formyl-2-hydroxyphenyl)methylideneamino]ethyliminomethyl]-2-hydroxybenzaldehyde
• CAS: 167103-32-4
• 化学式: C₁₈H₁₄Cl₂N₂O₄
• 分子量: 393.226
• InChiKey: JBMLGAVCEYMVJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  99.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  copper(II) perchlorate hexahydrate 、 N,N′-bis(3-formyl-5-chlorosalicylidene)ethylenediimine 、 N,N-bis(3-aminopropyl)-2-(thiophen-2-yl)ethylamine 在 三乙胺 作用下， 以 乙腈 、 水 为溶剂， 反应 6.0h， 以38%的产率得到
  参考文献：
  名称：

  Design, synthesis and crystal structure of six macrocyclic complexes as efficient and effective nitric oxide scavengers

  摘要：

  Four new complexes of Robson-type macrocycles, [CuH(L-1)](2)(ClO4)(2)(H2O)(2) (1), [CuH(L-2)] ClO4 (2), [Cu H (L-3)](2)(ClO4)(2) (3), [Cu H(L-4)](2)(ClO4)(2)(CH3CH2OH)(2)(CH3CN)(2)(4) and two reported Robson-type macrocycles polymers {[CuL5](H2O)(2)}(n), {[MnL5](H2O)(2)}(n) (6) were obtained. The ligands (H2L1, H2L2, H2L3) are the products from the condensation between bata and N,N'-bis(3-formyl-5-X-salicylimine)-1,2-ethylenediimine (X = CH3, Cl, F), respectively. Ligands H2L4 and H2L5 are the products of N,N'-bis(3-formyl-5-methylsalicylimine)-1,2-propylenediimineand condensation with bafa and bapa, respectively. All the metal ions have unsaturated coordinated sites, which are available for NO binding. The binding of the complexes with NO molecules have been confirmed by UV-Vis spectrophotometry. The binding constants were calculated to be 1.28 x 10(3) M-1, 8.9 x 10(2)M(-1), 7.7 x 10(3) M-1, 1.2 x 10(3)M(-1), 1.2 x 10(3)M(-1), 1.3 x 10(3)M(-1) for 1, 2, 3, 4, 5 and 6, respectively. The control experiments revealed there was non-reversible binding of NO, which can be ascribed to specially coordination environment of the central ions. Moreover, the interactions of the complexes with calf thymus DNA (CT-DNA) have been measured by agarose gel electrophoresis, and unobvious DNA cleavage ability of complexes 1, 3 and 4 indicating no damage to DNA. The results reveal that complexes 1, 3 and 4 can be served as potential NO scavengers. (C) 2018 Published by Elsevier Ltd.

  DOI：

  10.1016/j.poly.2018.08.061
• 作为产物：
  描述：

  2,6-二甲酰基-4-氯苯酚 、 乙二胺 以 乙醇 为溶剂， 反应 4.0h， 以57%的产率得到N,N′-bis(3-formyl-5-chlorosalicylidene)ethylenediimine
  参考文献：
  名称：

  Structure, DNA binding and cleavage of a new Zn(II)Mn(II) macrocyclic complex

  摘要：

  A new heterodinuclear complex of an unsymmetrical macrocycle [ZnMnL(CH3O)(2)]center dot H2O has been synthesized by the cyclocondensation between N,N'-bis(3-formyl-5-chlorosalicylidene)ethylenediimine and 2-hydroxyl-1,3-propanediamine in the presence of the metal ions, and characterized by elemental analyses, IR spectra and X-ray determination. The interactions of the complex with DNA have been investigated by UV absorption, fluorescence spectroscopy, viscosity measurements and electrochemical studies. Absorption spectroscopic investigation reveals that the complex has good binding propensity to calf thymus DNA by intercalation with a binding constant of 2.52 x 10(5) M-1. Fluorescence spectroscopy shows that the complex can displace ethidium bromide and bind to DNA, with a quenching constant of 4.37 x 10(3) M-1. The agarose gel electrophoresis studies show that pBR322 plasmid DNA can be transformed to nicked form and linear form in air by the complex. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.08.029

文献信息

• Design and synthesis of two macrocyclic dinuclear coordination polymers with binding of nitric oxide
  作者：Q.R. Cheng、M. Zhang、Y. Zhang、G.Y. Liao、H. Zhou、Z.Q. Pan

  DOI：10.1016/j.inoche.2016.06.033

  日期：2016.9

  [CuL1]n (1) and [CuL2]n (2), were obtained by the condensation between bapa and N,N′-bis(3-formyl-5-R-salicylimine)-1,2-propylenediimine in the presence of Cu(II). These polymers have the common feature that the 3-methylaminopyridine group in one ligand coordinates to the metal ion in the neighboring coordination unit, leading to the formation of one-dimensional infinite chain. The formation of NO

  摘要 通过 bapa 与 N,N'-bis(3-formyl-5- R-水杨亚胺)-1,2-丙烯二亚胺在Cu(II)存在下。这些聚合物的共同特点是一个配体中的3-甲基氨基吡啶基团与相邻配位单元中的金属离子配位，导致形成一维无限链。紫外/可见分光光度法证实了 NO 复合物的形成。1 和 2 的结合常数计算为 8.18 × 102 M- 1、1.2 × 103 M- 1。对照实验表明 NO 的不可逆结合可归因于中心 Cu(II) 离子的特殊配位环境。而且，用琼脂糖凝胶电泳测定了复合物与小牛胸腺 DNA (CT-DNA) 的相互作用，结果表明它们不能裂解 CT-DNA。这两种复合物可作为潜在的 NO 清除剂。图形摘要 Robson 型大环的两种新配位聚合物 [CuL1]n (1) 和 [CuL2]n (2)，是通过 bapa 与 N,N'-bis(3-formyl-5) 缩合获得的-R-水杨亚胺)-1