2-{N-(2-[2-pyridyl]ethyl)iminomethyl}-4-chlorophenol | 181932-37-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-{N-(2-[2-pyridyl]ethyl)iminomethyl}-4-chlorophenol
• 英文别名: N-(5-chlorosalicylideneaminato)-2-(2-aminoethyl)pyridine；4-chloro-2-((((2-pyridyl)ethyl)imino)methyl)phenol；4-Chloro-2-(2-pyridin-2-ylethyliminomethyl)phenol
• CAS: 181932-37-6
• 化学式: C₁₄H₁₃ClN₂O
• 分子量: 260.723
• InChiKey: SEPSJPPIUNLWEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 2-{N-(2-[2-pyridyl]ethyl)iminomethyl}-4-chlorophenol 以 甲醇 为溶剂， 以85 %的产率得到
  参考文献：
  名称：

  铜(II)复合功能化Fe3O4@ISNA（ISNA =异烟酸）作为磁性可恢复纳米材料的合成：醇氧化和硝基苯酚还原的催化研究以及TD-DFT研究

  摘要：

  两个新设计的配体，[4-氯-2-((((2-吡啶基)乙基)亚氨基)甲基)苯酚] ( HL 1 )和[4-溴-2-((((2-吡啶基)乙基)亚氨基)甲基)苯酚] ( HL 2 )，被选择合成两种 Cu(II) 二聚希夫碱配合物，[CuL 1 Cl] 2 ( 1 ) 和[CuL 2 Cl] 2 ( 2 )，目的是研究了它们对使用H 2 O 2作为末端氧化剂氧化醇和使用NaBH 4作为还原剂还原硝基芳烃的催化活性。使用物理化学技术和单晶 X 射线衍射对配合物进行了表征。还对这两种配合物进行了 DFT 计算。配合物[CuL 1 Cl] 2 ( 1 )在每个反应中都表现出较高的催化效率，因此选择它通过将其附着到表面改性的磁性纳米粒子来构建磁分离催化剂。然后，我们的目标是用氧化铁和异烟酸 (ISNA)进一步修饰配合物1 ，以便于磁分离。新型Fe 3 O 4 @ISNA@CuL 1催化剂进行了全面表征，包括

  DOI：

  10.1039/d3nj05440c
• 作为产物：
  描述：

  2-(2-氨乙基)吡啶 、 5-氯代水杨醛 以 甲醇 为溶剂， 生成 2-{N-(2-[2-pyridyl]ethyl)iminomethyl}-4-chlorophenol
  参考文献：
  名称：

  铜(II)复合功能化Fe3O4@ISNA（ISNA =异烟酸）作为磁性可恢复纳米材料的合成：醇氧化和硝基苯酚还原的催化研究以及TD-DFT研究

  摘要：

  两个新设计的配体，[4-氯-2-((((2-吡啶基)乙基)亚氨基)甲基)苯酚] ( HL 1 )和[4-溴-2-((((2-吡啶基)乙基)亚氨基)甲基)苯酚] ( HL 2 )，被选择合成两种 Cu(II) 二聚希夫碱配合物，[CuL 1 Cl] 2 ( 1 ) 和[CuL 2 Cl] 2 ( 2 )，目的是研究了它们对使用H 2 O 2作为末端氧化剂氧化醇和使用NaBH 4作为还原剂还原硝基芳烃的催化活性。使用物理化学技术和单晶 X 射线衍射对配合物进行了表征。还对这两种配合物进行了 DFT 计算。配合物[CuL 1 Cl] 2 ( 1 )在每个反应中都表现出较高的催化效率，因此选择它通过将其附着到表面改性的磁性纳米粒子来构建磁分离催化剂。然后，我们的目标是用氧化铁和异烟酸 (ISNA)进一步修饰配合物1 ，以便于磁分离。新型Fe 3 O 4 @ISNA@CuL 1催化剂进行了全面表征，包括

  DOI：

  10.1039/d3nj05440c

文献信息

• Cytotoxic oxidovanadium(IV) complexes of tridentate halogen‐substituted Schiff bases: First dinuclear V(IV) complexes with O → VIV = O → VIV = O core
  作者：Hadi Amiri Rudbari、Arezoo Saadati、Mahnaz Aryaeifar、Isabel Correia、Fernanda Marques、Olivier Blacque、Nicola Micale

  DOI：10.1016/j.bmcl.2021.128285

  日期：2021.10

  which revealed them as mono- and dinuclear vanadium(IV) complexes, respectively, with the ligands coordinated as bidentate chelates. The structure of 3 represents the first example of dinuclear V(IV) complex with O → VIV = O → VIV = O core (Cambridge Structural Database (CSD)​, version 5.42, update of May 2021). The cytotoxicity of ligands and complexes was evaluated towards ovarian (A2780), breast (MCF7)

  潜在的 N,N,O-三齿希夫碱配体 Cl-LH、Br-LH、BrCl-LH 和 H-LH 与 [V IV O(acac) 2 ] 以 2:1 的比例在甲醇中反应得到相应的单核和双核氧化钒(IV)配合物，VO(Cl-L) 2 (1), VO(Br-L) 2 (2), [(BrCl-L) 2 (H 2 O)V(μ-O) VO(BrCl-L) 2 ] (3) 和 [(HL) 2 (H 2 O)V(μ -O)VO(HL) 2 ] (4)，产率良好。通过元素分析和 FT-IR 光谱对配体和配合物进行了充分表征。配体还通过1 H NMR 光谱表征。V(IV)O 与 d 1的氧化态EPR 证实了所有合成复合物中的构型。此外，通过 X 射线衍射 (XRD) 分析确定了 2 和 3 的结构，表明它们分别为单核和双核钒 (IV) 配合物，配位体以双齿螯合物的形式配位。3 的结构代表了具有 O → V IV  =
• Electrochemical synthesis of manganese(II) and (III) complexes derived from alicylaldehyde and 2-(2-aminoethyl)pyridine
  作者：Lourdes Luaces、Manuel R. Bermejo、Jose A. Garcia-Vazquez、Jaime Romero、Antonio Sousa、Robin G. Pritchard、Charles A. McAuliffe、Yves Mugnier

  DOI：10.1016/0277-5387(96)00120-9

  日期：1996.8

  A series of manganese(II) and (III) complexes of tridentate NN′O donor set Schiff base ligands has been prepared by the electrochemical oxidation of a manganese anode in an acetonitrile solution of the Schiff bases (R-salaepH). These complexes are found to be of the form [Mn(R-salaep)2] and [Mn(R-salaep)2]CIO4. The single crystal X-ray structure of bis[2-(2-pyridyl)ethyll-iminomethyl-5-nitro-phenoxy}manganese(II)

  通过在Schiff碱的乙腈溶液（R-salaepH）中对锰阳极进行电化学氧化，制备了三齿NN'O供体组Schiff碱配体的一系列锰（II）和（III）配合物。发现这些络合物为[Mn（R-salaep）2 ]和[Mn（R-salaep）2 ] CIO 4的形式。测定了双[2-（2-吡啶基）乙基-亚氨基甲基-5-硝基-苯氧基}锰（II）的单晶X射线结构。在以0.2 M Bu 4 NPF 6为支持电解质的二氯甲烷溶液中，锰（II）配合物[Mn（R-salaep）2 l的单电子氧化产生其相关的锰（III）配合物[Mn（R-salaep ）2 ] PF 6。
• Vanadium(V) Pyridine‐Containing Schiff Base Catecholate Complexes are Lipophilic, Redox‐Active and Selectively Cytotoxic in Glioblastoma (T98G) Cells
  作者：Kateryna Kostenkova、Aviva Levina、Drew A. Walters、Heide A. Murakami、Peter A. Lay、Debbie C. Crans

  DOI：10.1002/chem.202302271

  日期：2023.12.6

  Two new series of complexes with pyridine‐containing Schiff bases, [V^VO(SALIEP)L] and [V^VO(Cl‐SALIEP)L] (SALIEP=N‐(salicylideneaminato)‐2‐(2‐aminoethylpyridine; Cl‐SALIEP=N‐(5‐chlorosalicylideneaminato)‐2‐(2‐aminoethyl)pyridine, L=catecholato(2−) ligand) have been synthesized. Characterization by ¹H and ⁵¹V NMR and UV‐Vis spectroscopies confirmed that: 1) most complexes form two major geometric isomers in solution, and [V^VO(SALIEP)(DTB)] (DTB=3,5‐di‐tert‐butylcatecholato(2−)) forms two isomers that equilibrate in solution; and 2) tert‐butyl substituents were necessary to stabilize the reduced V^IV species (EPR spectroscopy and cyclic voltammetry). The pyridine moiety within the Schiff base ligands significantly changed their chemical properties with unsubstituted catecholate ligands compared with the parent HSHED (N‐(salicylideneaminato)‐N′‐(2‐hydroxyethyl)‐1,2‐ethanediamine) Schiff base complexes. Immediate reduction to V^IV occurred for the unsubstituted‐catecholato V^V complexes on dissolution in DMSO. By contrast, the pyridine moiety within the Schiff base significantly improved the hydrolytic stability of [V^VO(SALIEP)(DTB)] compared with [V^VO(HSHED)(DTB)]. [V^VO(SALIEP)(DTB)] had moderate stability in cell culture media. There was significant cellular uptake of the intact complex by T98G (human glioblastoma) cells and very good anti‐proliferative activity (IC₅₀ 6.7±0.9 μM, 72 h), which was approximately five times higher than for the non‐cancerous human cell line, HFF‐1 (IC₅₀ 34±10 μM). This made [V^VO(SALIEP)(DTB)] a potential drug candidate for the treatment of advanced gliomas by intracranial injection.

  摘要 合成了两个新系列的含吡啶席夫碱配合物，即[VVO(SALIEP)L]和[VVO(Cl-SALIEP)L]（SALIEP=N-(水杨基亚氨基)-2-(2-氨基乙基)吡啶；Cl-SALIEP=N-(5-氯水杨基亚氨基)-2-(2-氨基乙基)吡啶，L=邻苯二酚（2-）配体）。通过 1H 和 51V NMR 以及 UV-Vis 光谱的表征证实了以下几点：1) 大多数配合物在溶液中形成两种主要的几何异构体，而[VVO(SALIEP)(DTB)]（DTB=3,5-二叔丁基邻苯二酚（2-））在溶液中形成两种平衡的异构体；以及 2) 叔丁基取代基是稳定还原 VIV 物的必要条件（EPR 光谱和循环伏安法）。与母体 HSHED（N-（水杨醛氨基）-N′-（2-羟乙基）-1,2-乙二胺）席夫碱配合物相比，席夫碱配体中的吡啶基与未取代的儿茶酚配体相比，其化学性质发生了显著变化。未取代的邻苯二酚 VV 复合物在二甲基亚砜中溶解后立即还原成 VIV。相比之下，与[VVO(HSHED)(DTB)]相比，席夫碱中的吡啶分子大大提高了[VVO(SALIEP)(DTB)]的水解稳定性。[VVO(SALIEP)(DTB)]在细胞培养基中具有中等稳定性。T98G（人胶质母细胞瘤）细胞对完整复合物有明显的细胞吸收，并具有很好的抗增殖活性（IC50 6.7±0.9 μM，72 小时），比非癌症人细胞株 HFF-1 的活性（IC50 34±10 μM）高出约五倍。这使得[VVO(SALIEP)(DTB)]成为通过颅内注射治疗晚期胶质瘤的潜在候选药物。
• Mn(III) and Mn(II) complexes of tridentate Schiff base ligands; synthesis, characterization, structure, electrochemistry and catalytic activity
  作者：Rita N. Egekenze、Yilma Gultneh、Ray Butcher

  DOI：10.1016/j.ica.2018.01.027

  日期：2018.6

  Three Mn(III) complexes [Mn(L-1)(2)] (ClO4)1, [Mn(L-2)(2)] (ClO4)2, [Mn(L-3)(2)] (ClO4)3, and one Mn(II) complex [Mn(L-4)(2)]4 were studied for their efficiency as catalysts for epoxidation of olefins with H2O2 at room temperature and 0 degrees C in the presence of ammonium acetate-acetic acid or triethylamine-perchloric acid system as co-catalyst/buffer. The complexes were obtained from the reaction of Mn(ClO4)(2)center dot 6H(2)0 with NNO tridentate Schiff base ligands HL1-HL4 synthesized from the condensation reaction of 2-(2-aminoethyl) pyridine and 2-hydroxybenzaldehyde (HL1), 5-chloro-2-hydroxybenzaldehyde (HL2), 5-methoxy- 2-hydroxybenzaldehyde (HL3), or 5-nitro-2-hydroxybenzaldehyde (HL4) respectively. The complexes were characterized by spectroscopic techniques as well as by single crystal X-ray diffraction analysis. Electronic effect of the substituents on epoxide yield was also investigated. The crystal structures of complexes confirm coordination of the manganese ion to the ligands through the NNO atoms of the ligands. The spectral changes observed as a function of time for the reaction of the complexes with aqueous (30%) hydrogen peroxide indicates possible formation of an intermediate product; hydroperoxo-complex implicated in the epoxidation reaction. The complexes catalyzed epoxidation of cyclohexene with low yield at room temperature but higher yield at 0 degrees C in the order complex 3 lower than 1, 1 lower than 2, with the Mn(II) complex 4 recording highest epoxide yield of 9% with turnover of 2.25 at room temperature and yield of 58% with turnover of 14.5 at 0 degrees C in the presence of ammonium acetate-acetic acid system/buffer. With the triethylamine-perchloric acid system/buffer, epoxide yield of 46% and turnover of 11.5 was recorded at room temperature while 44% with turnover of 11.0 was obtained at 0 degrees C for complex 4. (C) 2018 Elsevier B.V. All rights reserved.