N-(pyridine-2-ylethyl)-2-hydroxy-5-nitro-benzylideneamine | 101079-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(pyridine-2-ylethyl)-2-hydroxy-5-nitro-benzylideneamine
• 英文别名: 2-{N-(2-[2-pyridyl]ethyl)iminomethyl}-4-nitrophenol；(2-hydroxy-5-nitrobenzyl)(2-(pyrid-2-yl)ethyl)imine
• CAS: 101079-17-8
• 化学式: C₁₄H₁₃N₃O₃
• 分子量: 271.276
• InChiKey: SEPUIGAXEUPNSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  88.62
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(pyridine-2-ylethyl)-2-hydroxy-5-nitro-benzylideneamine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (2-hydroxy-5-nitrobenzyl)(2-(pyrid-2-yl)ethyl)amine
  参考文献：
  名称：

  A series of mononuclear Co(III) complexes using tridentate N,O-donor ligands: Chemical properties and cytotoxicity activity

  摘要：

  Continuing our interest in tridentate ligands to develop new prototypes of cobalt-based metallodrugs for combating cancer, modifications in the backbone of HL1, [(2-hydroxybenzyl)(2-(pyridil-2-yl]ethyl)amine) were proposed in order to modulate the redox potential of new Co(III) complexes. Three ligands with electron withdrawing groups were synthesized: HL2: [(2-hydroxy-5-nitrobenzyl)(2-(pyridil-2-yl)ethyl]amine); HL3: [(2-hydroxybenzyl)(2-(pyridil-2-yl)ethyl]imine) and HL4: [(2-hydroxy-5-nitrobenzyl)(2(pyridil-2-yl)ethyl]imine). They were used to obtain the respective mononuclear complexes 2, 3 and 4, which are discussed compared to the previous reported complex 1 (obtained from HL1). The new complexes were characterized and studied by several techniques including X-ray crystallography, elemental and conductimetric analysis, IR, UV-vis and H-1 NMR spectroscopies, and electrochemistry. The substitutions of the group in the para position of the phenol (HL1 and HL2) and the imine instead of the amine (HL3 and HL4), promote anodic shifts in the complexes reduction potentials. The influence of these substitutions in the biological activities of the Co(III) complexes against the murine melanoma cell line (B16F10) was also evaluated. Little effect was observed on cellular viability decrease for all free ligands, however the coordination to Co(III) enhances their activities in the following range: 1>4 approximate to 2>3. The data suggest that no straight correlation can be addressed between the reduction potential of the Co(III) center and the cell viability. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2011.09.011
• 作为产物：
  描述：

  2-(2-氨乙基)吡啶 、 5-硝基水杨醛 以 甲醇 为溶剂， 以86%的产率得到N-(pyridine-2-ylethyl)-2-hydroxy-5-nitro-benzylideneamine
  参考文献：
  名称：

  六配位铁 (III) 配合物的合成、表征和形成常数

  摘要：

  十二个铁 (III) 配合物 [FeIII(LX)2]ClO4，其中 (LX)− 是一系列包含吡啶和取代苯酚部分的不对称配体的去质子化形式 (XPh(OH)–CH=N–(CH2) n –Py，X = H, 5-Br, 5-NO2, 5-OMe, 4-OMe, 3-OMe, and n = 1, 2), 合成并通过 1H NMR、IR、UV-Vis 光谱表征，质谱和元素分析。在恒定离子强度 (0.10 M NaClO4) 和 25 (±0.1)°C 下，使用紫外-可见分光光度法滴定测量形成常数。Fe(III) 离子与给定的三齿配体形成络合物的趋势如下：

  DOI：

  10.1080/00958970903302681

文献信息

• 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。
• Homoleptic phenoxy-imine pyridine zinc complexes: efficient catalysts for solvent free synthesis and chemical degradation of polyesters
  作者：Sara D'Aniello、Sidonie Laviéville、Federica Santulli、Malaury Simon、Michele Sellitto、Consiglia Tedesco、Christophe M. Thomas、Mina Mazzeo

  DOI：10.1039/d2cy01092e

  日期：——

  The synthesis and structural characterization of six homoleptic zinc complexes supported by monoanionic phenoxy-imine pyridine ligands bearing different substituents on the phenoxy moiety are described. All complexes have been tested as catalysts for the ring-opening polymerization of L-lactide under mild or industrially relevant conditions using technical grade L-lactide and excess alcohol. Interestingly

  描述了由在苯氧基部分具有不同取代基的单阴离子苯氧基-亚胺吡啶配体支持的六种均配锌配合物的合成和结构表征。在温和或工业相关条件下，使用工业级L-丙交酯和过量醇对所有配合物作为L-丙交酯开环聚合的催化剂进行了测试。有趣的是，Zn( II) 催化剂在恶劣条件下是稳定的，显示出与工业催化剂相当的活性。同样的配合物也被发现在聚丙交酯和聚（对苯二甲酸乙二醇酯）的醇解解聚中具有活性。对于这两个过程，都发现了结构-反应性关系，这取决于在配体主链上引入的取代基。进行了无溶剂醇解中催化剂回收的测试，为通过低环境影响程序实施循环（生物）塑料经济提供了新的机会。
• 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.
• Complexation of Group IIIA metals with asymmetric tridentate ligands: Synthesis, characterization, formation constants and cytotoxicity
  作者：Mozaffar Asadi、Maryam Mohammadikish、Khosro Mohammadi、Pegah Mousavi、Katayon Javidnia、Ramin Miri

  DOI：10.1016/j.ica.2009.07.021

  日期：2009.11

  A series of new aluminum(III), gallium(III) and indium(III) complexes with some tridentate Schiff base, viz., N-pyridine-2-ylmethyl}-2-hydroxy-5-methoxy-benzylideneamine [HL1], N-pyridine-2-ylmethyl}-2-hydroxy-benzylideneamine [HL2], N-pyridine-2-ylmethyl}-2-hydroxy-5-nitro-benzylideneamine [HL3], N-pyridine-2-ylmethyl}-2-hydroxy-5-bromo-benzylideneamine [HL4], N-pyridine-2-ylethyl}-2-hydroxy-5-methoxy-benzylideneamine [HL5], N-pyridine-2-ylethyl}-2-hydroxy-benzylideneamine [HL6], N-pyridine-2-ylethyl}-2-hydroxy-5-nitro-benzylideneamine [HL7], N-pyridine-2-ylethyl}-2-hydroxy-5-bromo-benzylideneamine [HL8], with the general formula [ML2][Y] (M = Al3+, Ga3+, In3+; Y = NO3, ClO4) were synthesised and characterized by elemental analysis, H-1 NMR, FT-IR, UV-Vis spectrophotometry and mass spectrometry. The thermodynamic formation constants of the complexes were determined spectrophotometrically at constant ionic strength (I = 0.10 M NaClO4) and at 25 degrees C in methanol. The trend of formation constants of the complexes are as follow:Al < Ga < In5-OMe > 5-H > 5-NO2 > 5-BrAlso, their cytotoxic activities were evaluated in four various cell lines which showed their moderate cytotoxic effect. (c) 2009 Elsevier B.V. All rights reserved.