N-2-pyridylmethylidene-2-hydroxy-5-chlorophenylamine | 20211-18-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-2-pyridylmethylidene-2-hydroxy-5-chlorophenylamine
• 英文别名: 4-chloro-2-(2-pyridylaldimine)phenol；4-chloro-2-((pyridin-2-ylmethylene)amino)phenol；N-2-pyridiylmethylidene-2-hydroxy-5-chloro-phenylamine；2-(picolinylideneamino)-4-chloro-phenol；4-Chloro-2-(pyridin-2-ylmethylideneamino)phenol
• CAS: 20211-18-1
• 化学式: C₁₂H₉ClN₂O
• 分子量: 232.669
• InChiKey: VDEKVCGAAMUACI-UHFFFAOYSA-N

物化性质

• 沸点：
  447.4±40.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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 、 N-2-pyridylmethylidene-2-hydroxy-5-chlorophenylamine 在 KOH 作用下， 以 甲醇 为溶剂， 生成 [Cu(2-(picolinylideneamino)-4-chloro-phenolato)Cl]
  参考文献：
  名称：

  具有2-N-（吡啶甲基）-nR-酚的铜（II）配合物：溶剂致变色，自组装和超分子结构

  摘要：

  一系列具有[Cu（n-R -pyp）X]的铜（II）配合物，带有N，N，O供体Schiff碱体系2- N-（吡啶甲基）-n-R-苯酚（n-合成了作为辅助配体的R -Hpyp（当R = Me时，n = 3、4、5和6，当R = Cl时，n = 4）和卤化物（X-= Cl-或Br-）。该复合物的特征在于显微分析，磁性和各种光谱测量。它们表现出溶剂变色行为。确定所有配合物的单晶X射线结构。在诸如方形-平面配合物之类的配位不饱和物种中，金属离子可以与第五个原子相互作用，如果该原子与金属键合，则会形成二聚体或聚合聚集体。在当前的一系列配合物中，当存在分子间Cu···X相互作用时，金属离子为方平面和扭曲的方锥体。除了这种Cu···X相互作用外，还存在分子间弱非共价相互作用，即O–H···O，C–H···O，CH–H···X和π···π感知到的。这些复合物的分子通过这些相互作用形成的超分子结构被仔细研究

  DOI：

  10.1016/j.ica.2010.03.072
• 作为产物：
  描述：

  吡啶-2-甲醛 、 4-氯-2-氨基苯酚 以 甲醇 为溶剂， 反应 0.5h， 以83%的产率得到N-2-pyridylmethylidene-2-hydroxy-5-chlorophenylamine
  参考文献：
  名称：

  4-氯-2-((吡啶-2-基亚甲基)氨基)苯酚衍生的铜、镍和锌配合物的合成、晶体结构和脲酶抑制

  摘要：

  摘要 一系列铜、镍和锌络合物，[CuClL] ( 1 )、[CuBrL] ( 2 )、[NiL 2 ] ( 3 )、[ZnL 2 ] ( 4 ) 和 [Zn 2 I 2 L 2 ] ( 5 )，其中 L 是 4-氯-2-((吡啶-2-基亚甲基)氨基)苯酚的去质子化形式，已经合成并通过元素分析、IR 和 UV-Vis 光谱进行了表征。通过单晶X射线衍射进一步证实了配合物的结构。1和2中的Cu离子呈正方形平面配位。3和4中的 Ni 和 Zn 离子是八面体配位的。中心对称配合物5中 Zn 离子的配位介于方锥体和三角双锥体之间。铜络合物具有优异的脲酶抑制活性。

  DOI：

  10.1080/00958972.2022.2032005

文献信息

• cis-{MoO₂}²⁺ assisted Mannich-type addition of acetylacetonate methine to the azomethine of tridentate Schiff bases: racemic complexes with chiral transformed ligands
  作者：Sathish Kumar Kurapati、Samudranil Pal

  DOI：10.1039/c4dt03187c

  日期：——

  electrochemical measurements. The molecular structures of all the complexes except for 5 are authenticated by single crystal X-ray crystallography. The Mo(VI) center in each of these analogous complexes is in a distorted octahedral N2O4 coordination sphere assembled by the chiral N2O2-donor transformed ligand (acacLn)2− and the two mutually cis-oriented oxo ligands. In the crystal lattice, each of 1–4 exists

  [的MoO的反应2（ACAC）2 ]（ACAC - =乙酰丙酮化物）与潜在的N 2 O-供5,5-元稠合螯合环形成席夫碱的2-（2- pyridylaldimine）乙醇（HL 1）和4 / 5- R -2-（2-吡啶基亚二胺）酚（HL n；对于R = H，4-Cl，4-Me和5-Me分别为n = 2–5 ）导致容易形成外消旋体的外消旋复合物。通式cis- [MoO 2（aCACL 1-5）]（1-5），产率80-85％。在此，（aCACL n）2-表示手性N 2 O由新颖的曼尼希型反应形成的2-供体配体系统，该反应涉及乙酰丙酮化物和HL n的偶氮甲基片段，两者均与顺式-MoO 2 } 2+单元配位。1-5的表征已通过微分析（CHN），光谱法（ESI-MS，IR，UV-Vis以及1 H和13 C-NMR）和电化学测量进行了。除5以外的所有配合物的分子结构均通过单晶X射线晶体学鉴定。这些类似复合物中每个的Mo（
• Preparation and structures of trinuclear manganese(II) complexes with N-2-pyridiylmethylidene-2-hydroxy-5-substituted-phenylamine
  作者：Hideyuki Asada、Katsuya Hayashi、Sei Negoro、Manabu Fujiwara、Takayuki Matsushita

  DOI：10.1016/s1387-7003(02)00718-9

  日期：2003.2

  Abstract The trinuclear manganese(II) complexes, [MnII3(OAc)4(pap)2(H2O)2] and [MnII3(OAc)4(5-Cl-pap)2(MeOH)2] were prepared by the reaction of tridentate Schiff base ligands X-papH (X=H, Cl), [N-2-pyridiylmethylidene-2-hydroxy-5-substituted-phenylamine], and MnII(OAc)2·2H2O. In the molecular structures of these complexes, two terminal manganese ions are coordinated with one oxygen and two nitrogen

  摘要 通过以下反应制备了三核锰(II)配合物[MnII3(OAc)4(pap)2(H2O)2]和[MnII3(OAc)4(5-Cl-pap)2(MeOH)2]。三齿席夫碱配体 X-papH (X=H, Cl)、[N-2-pyridiylmethylidene-2-hydroxy-5-located-phenylamine] 和 MnII(OAc)2·2 。在这些配合物的分子结构中，两个末端锰离子与X-pap的一个氧和两个氮原子、OAc-的两个氧原子和一个溶剂分子配位，形成扭曲的八面体结构，其中中心锰离子驻留在一个对称中心，周围环绕着来自四个桥接 OAc− 的四个氧原子的 O6 供体组和两个 X-pap 配体的两个酚氧原子。
• Dinuclear heptacoordinate dibutyltin (IV) complexes derived from Schiff bases and dicarboxylates: Synthesis, cytotoxicity, and antioxidant activity
  作者：Alejandro Ramírez-Jiménez、Rolando Luna-García、Armando Cortés-Lozada、Simón Hernández、Teresa Ramírez-Apan、Antonio Nieto-Camacho、Elizabeth Gómez

  DOI：10.1016/j.jorganchem.2013.03.038

  日期：2013.8

  The synthesis of dinuclear dibutyltin (IV) complexes 1a-4d, prepared in one pot by the reaction of 2-amino-4-R-phenol (R = H, Me, Cl, NO2), 2-pyridinecarboxaldehyde, dicarboxylic (2,5-pyridinedicarboxylic, terephthalic, isophthalic, and oxalic) acids and dibutyltin oxides, is described. The complexes were characterized using IR, MS and H-1, C-13 and Sn-119 NMR techniques. The molecular structures of complexes 1a, 1c and 4c were established using X-Ray diffraction, and these complexes exhibited a distorted pentagonal-bipyramidal (BPT) geometry in which the equatorial plane consisted of three oxygen atoms and two nitrogen atoms, and the butyl groups occupied the axial positions. The cytotoxicity of the terephthalic acid derivatives 1a-d in HCT-15 colon cancer, MCF7 breast cancer and PC3 prostate cancer cell lines was investigated in vitro. The antioxidant activity of these complexes was also measured using the DPPH (1,1-diphenyl-2-picrylhydrazyl) assay. (C) 2013 Elsevier B. V. All rights reserved.
• Complexes of functionalised phosphine ligands. Part 1. Complexes of Fe^III, Co^III, Ni^IIand Re^Vwith tridentate Schiff bases having PNO, NNO and NNS donor sets. Crystal structures of 2-(Ph₂PC₆H₄NCH)C₆H₄OH and [Co{2-(Ph₂PC₆H₄CHN)C₆H₄O}₂][PF₆]
  作者：Jonathan R. Dilworth、Stuart D. Howe、Antony J. Hutson、John R. Miller、Jack Silver、Russell M. Thompson、Mary Harman、Michael B. Hursthouse

  DOI：10.1039/dt9940003553

  日期：——

  The Schiff bases 2-[Ph(2)P(CH2)(n)N=CH] C6H4OH (n = 3, HL(1) or 2 HL(2)), 2-(RCH=N)C6H3(OH)X-4 (R = 2-Ph(2)PC(6)H(4), X = H HL(3); R = 2-C5H4N, X = H HL(4); R = 2-C5H4N. X = Cl HL(5)) were synthesised from the appropriate amine and aldehyde. On deprotonation these all functioned as tridentate monoanionic ligands to give complexes [FeL(2)](+) and [CoL(2)]+ with Fe-III and Co-III and neutral complexes of stoichiometry NiL(2) with Ni-II. The iron complexes were examined by Mossbauer spectroscopy which indicated the presence of two iron sites in [FeL(2)(1)](+) with a spin-state equilibrium dependent on both temperature and the counter ion. The complex [FeL(2)(3)](+) showed a single iron site, again with a spin state dependent on counter ion and temperature. The crystal structures of HL(3) and [CoL(2)(3)](+) have been determined. The distortions in free HL(3) predispose it for co-ordination in a fac geometry to the Co with cis-PPh(2) groups, and the changes occurring on co-ordination are discussed in detail. Reaction of RCHO (R = 2-Ph(2)PC(6)H(4) or 2-C5H4N) with 2-aminobenzenethiol gave stable thiazoles RCHNHC(6)H(4)S-2 which did not ring open to give tridentate ligands even on reaction with base and/or metal ions.
• Synthesis, structure, protein binding, and cytotoxicity of zinc(II) complexes with tridentate NNO Schiff-base ligands
  作者：Mei Li、Yi Gou、Yao Zhang、Feng Yang、Hong Liang

  DOI：10.1080/00958972.2014.903328

  日期：2014.3.19

  Mononuclear and trinuclear zinc(II) complexes (1 and 2) with tridentate NNO Schiff-base ligands (HL1 = N-2-pyridiylmethylidene-4-chloro-2-hydroxy-phenylamine, HL2 = N-2-pyridiylmethylidene-2-hydroxy-5-chloro-phenylamine) have been synthesized and characterized by single-crystal X-ray diffraction and elemental analysis. The binding properties of zinc(II) complexes with calf thymus DNA (CT-DNA) and HSA were investigated by UV-visible, fluorescence, and circular dichroism spectra. The zinc(II) complexes bind significantly to CT-DNA by intercalation and bind to protein HSA through a static quenching mechanism. The in vitro cytotoxicity of the complexes on human tumor cells lines was assessed by 3-(4,5-dimathylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide, Hoechst 33258 staining experiments.