2,6-bis-[(2-hydroxy-ethylimino)-methyl]-4-methyl phenol | 174504-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,6-bis-[(2-hydroxy-ethylimino)-methyl]-4-methyl phenol
• 英文别名: 6-{[(2-Hydroxyethyl)amino]methylidene}-2-{(E)-[(2-hydroxyethyl)imino]methyl}-4-methylcyclohexa-2,4-dien-1-one；2,6-bis(2-hydroxyethyliminomethyl)-4-methylphenol
• CAS: 174504-82-6
• 化学式: C₁₃H₁₈N₂O₃
• 分子量: 250.298
• InChiKey: DRDQUJMHLOOUKI-UHFFFAOYSA-N

物化性质

• 熔点：
  145 °C
• 沸点：
  464.0±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-bis-[(2-hydroxy-ethylimino)-methyl]-4-methyl phenol 、 copper(II) acetate monohydrate 以 乙腈 为溶剂， 反应 1.75h， 以72%的产率得到
  参考文献：
  名称：

  Synthesis, characterization and catalytic properties of multinuclear copper(II) complexes

  摘要：

  Four tetranuclear [Cu-4(O)(L-n)(2)(CH3COO)(4)] (1, 2, 4 and 5) and one pentanuclear [Cu-5(OH)(2)(L-3)(2)(CH3COO)(6)] (3) with N2O-donor Schiff-base ligands have been synthesized, where HL1 = 4-methyl-2,6-bis(2-hydroxyethyliminomethyl)phenol for complex 1, HL2 = 4-methyl-2,6-bis(3-hydroxypropyliminomethyl)phenol for complex 2, HL3 = 4-methyl-2,6-bis(4-hydroxybutyliminomethyl)phenol for complex 3, HL4 = 4-methyl-2,6-bis(5-hydroxypentyliminomethyl)phenol for complex 4 and HL5 = 4-methyl-2,6-bis(6-hydroxyhexyliminomethyl)phenol for complex 5. These complexes have been characterized by elemental analysis, FT-IR, UV-Vis spectroscopy. The structures of 1, 3, 4 and 5 have been determined by single crystal X-ray diffraction studies. X-ray analysis reveals that complexes 1, 4 and 5 are mu(4)-oxido-bridged tetrameric copper(II) complexes, where four copper atoms arrange themselves around an oxidooxygen atom at the vertices of a distorted tetrahedron. The pentanuclear complex, 3, has been found to have two mu(3)-hydroxido bridging ligands each connecting three copper atoms. These complexes have been employed as catalyst for the epoxidation of olefins in the presence of tert-butyl hydroperoxide (TBHP) as the oxidant under mild conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.04.028
• 作为产物：
  描述：

  2-氨基乙醛 、 2,6-二甲酰-4-甲基苯酚 以 乙醇 为溶剂， 反应 5.0h， 以74%的产率得到2,6-bis-[(2-hydroxy-ethylimino)-methyl]-4-methyl phenol
  参考文献：
  名称：

  双核铜（II）配合物的酪氨酸酶和儿茶酚酶样活性

  摘要：

  摘要合成了一种双核Cu（II）配合物，并进行了晶体学表征。发现该化合物在分子的Cu（II）中心之间具有反铁磁相互作用。它具有弱的分子间铁磁相互作用。发现该化合物具有酪氨酸酶和儿茶酚酶活性。在酪氨酸酶活性的情况下，使用薄层色谱法（TLC）分离形成的双酚，并通过1 H NMR和质谱进行表征。使用GC-MS对在该反应中形成的邻醌衍生物进行了表征。用分光光度法监测后者的活性，并色谱分离（在MeOH和MeCN中）邻邻苯二酚衍生物产物，并使用熔点测定对其进行表征。其次是米歇利斯-门腾动力学，其周转率分别为4.95×103和1。

  DOI：

  10.1016/j.poly.2017.11.040

文献信息

• Coordination induced fluorescence enhancement and construction of a Zn₃constellation through hydrolysis of ligandimine arms
  作者：Avijit Sarkar、Aloke Kumar Ghosh、Valerio Bertolasi、Debashis Ray

  DOI：10.1039/c1dt11390a

  日期：——

  The phenoxido and alkoxido bridged neutral Zn3 complex [Zn3(μ-H2bemp)2(μ3-emp)2] (1), with an angular Zn3(μ-OPh)2(μ-OEt)2 core and capping nitrogen donors, was synthesized via simultaneous chelation-cum-bridging of the parent and hydrolysed ligands. Zinc(II) coordination triggered the solution phase imine (CN) bond hydrolysis of H3bemp (2,6-bis-[(2-hydroxyethylimino)methyl]-4-methylphenol) and yielded the unexpected angular trinuclear Zn(II) complex 1, having structural similarity with the Zn3 active site of P1 nuclease. H3bemp also displays a zinc(II) selective chelation-enhanced fluorescence response from strong metal ion coordination. Complexation of zinc(II) with H3bpmp (2,6-bis-[(3-hydroxypropylimino)methyl]-4-methylphenol), a close analogue of H3bemp, instead provides only mononuclear [Zn(H2bpmpHN)2](ClO4)2·2H2O (2·2H2O) (HN is the proton attached to an imine nitrogen atom) of two zwitterionic ligands, generated through a kind of coordination driven acid–base reaction, without showing any aggregation reaction. As the sole metal–organic precursor, both the complexes under pyrolytic conditions give ZnO nano structures of two morphologies.

  含有角形Zn_3(μ-OPh)_2(μ-OEt)_2核心及封端氮供体的中性Zn_3配合物[Zn_3(μ-H_2bemp)_2(μ_3-emp)_2]（1）通过母体及水解型配体的同步螯合桥连作用合成。锌(II)配合导致H_3bemp(2,6-双[(2-羟乙基亚氨基)甲基]-4-甲基苯酚)溶液相亚胺(CN)键水解,并且产生具有与P_1核酸酶活性中心Zn_3相似结构的角形Zn(II)三核配合物1。H_3bemp同样表现为由强金属离子配合所产生的金属离子选择型螯合增强荧光响应。H_3bpmp(2,6-双[(3-羟丙基亚氨基)甲基]-4-甲基苯酚,为H_3bemp的结构类似物)与锌(II)的配位产物只是双两性离子配体通过配合驱动的酸碱反应所产生的单核[Zn(H_2bpmpHN)_2](ClO_4)_2·2H_2O(2·2H_2O)（HN是连接在亚胺氮原子上的质子）,没有表现出任何聚集反应。作为唯一的金属-有机前驱体,在热解条件下,通过这两种配合物均得到两种形貌的ZnO纳米结构。
• Solvent dependent ligand transformation in a dinuclear copper(<scp>ii</scp>) complex of a compartmental Mannich-base ligand: synthesis, characterization, bio-relevant catalytic promiscuity and magnetic study
  作者：Ishani Majumder、Prateeti Chakraborty、Sudhanshu Das、Hulya Kara、Shymal Kumar Chattopadhyay、Ennio Zangrando、Debasis Das

  DOI：10.1039/c5ra05776k

  日期：——

  Bio-relevant catalytic promiscuity of a dicopper(ii) complex has been investigated with reference to catecholase and phosphatase activities. Solvent dependent ligand transformation associated with dealkylation followed by redox reaction is explored.

  一种二铜（II）配合物的生物相关催化杂活性已经针对邻苯二酚酶和磷酸酶活性进行了研究。与去烷基化相关的溶剂依赖性配体转化，随后进行氧化还原反应的探索。
• A novel water-soluble tetranuclear copper (II) Schiff base cluster bridged by 2, 6-bis-[(2-hydroxyethylimino)methyl]-4-methylphenol in interaction with BSA: Synthesis, X-ray crystallography, docking and cytotoxicity studies
  作者：Zahra Asadi、Maryam Golchin、Vaclav Eigner、Michal Dusek、Zahra Amirghofran

  DOI：10.1016/j.jphotochem.2018.05.016

  日期：2018.6

  activity against the cultured tumor cells was observed which makes the complex a possible candidate as an anticancer agent. Further investigation of the BSA-complex interactions was done by docking studies.

  由2,6-双-[（2-羟乙基亚氨基）甲基] -4-甲基苯酚桥接的水溶性四核铜席夫碱络合物，即[Cu 4（L 1）2（O）（OAc）4 ] ·2H 2 O的合成。该复合物的特征是1HNMR，FT-IR，元素分析和单晶X射线衍射。晶体结构分析表明，四个Cu原子以扭曲的四面体几何形状位于中心O原子周围。除两个配体外，四个乙酸盐还桥接了四个Cu原子。通过吸收和发射滴定法探索了该复合物与牛血清白蛋白（BSA）的相互作用，计算的结合常数显示该复合物对BSA的高亲和力。通过MTT比色法评估该复合物对Jurkat，Raji和A549细胞系的抗肿瘤活性。观察到针对培养的肿瘤细胞的强活性，这使得该复合物成为抗癌剂的可能候选物。通过对接研究对BSA-复杂的相互作用进行了进一步的研究。
• Interaction with DNA of a heteronuclear [Na2Cu4] coordination cluster obtained from the assembly of two hydroxo-bridged [CuII2] units by a dimeric sodium nitrate template
  作者：Debashree Mandal、Mala Chauhan、Farukh Arjmand、Guillem Aromí、Debashis Ray

  DOI：10.1039/b909249h

  日期：——

  [Na(2)Cu(4)(bemp)(2)(OH)(2)(NO(3))(2)(OH(2))(4)] x 5 H(2)O (1 x 5H(2)O; H(3)bemp: 2,6-bis-[(2-hydroxyethylimino)-methyl]-4-methyl-phenol) cluster has been synthesized in aqueous-methanol at room temperature and structurally characterized. The water soluble complex is obtained from the template assembly of two [Cu(2)(bemp)(OH)] neutral fragments through their weak oxophillic interactions with two interconnected

  异核[Na（2）Cu（4）（bemp）（2）（OH）（2）（NO（3））（2）（OH（2））（4）] x 5 H（2）O（ 1 x 5H（2）O; H（3）bemp：在室温下于甲醇水溶液中合成了2,6-双-[（（2-羟乙基亚氨基）-甲基] -4-甲基-苯酚）簇，并对其结构进行了表征。水溶性复合物是通过两个中性[Cu（2）（bemp）（OH）]中性片段的模板组装体，通过它们与两个相互连接的NaNO（3）单元的弱亲氧相互作用而获得的。四个[Na（2）Cu（4）]单元在捕获（H（2）O）（7）簇的晶格中形成金属有机笼排列。可变温度磁化率测量值（2-300 K）显示在J = -124.1 cm（-1）的二聚体中的Cu（II）离子之间有很强的反铁磁耦合（在H = -2JS（1）S（2 ） 习​​俗）。通过紫外可见分光光度法和发射滴定法研究了1x 3H（2）O与小牛胸腺DNA（结合常数K（b），4.6
• Fluorometric sensing of thiocyanate ions and competitive binding of anions in a family of CdII complexes of a phenol based ligand showing diverse structures
  作者：Avijit Sarkar、Valerio Bertolasi、Debashis Ray

  DOI：10.1016/j.poly.2012.06.088

  日期：2012.8

  A family of central phenoxido and terminal alcohol bound Cd-2 complexes have been synthesized and crystallographically characterized. Reaction condition and anion coordination (NO3-, NCS- and N-3(-)) dependent changeable structures have been identified in the four complexes 1-4 following varying coordination of the binucleating Schiff base ligand H(3)bemp (2,6-bis[(2-hydroxy ethylimino)-methyl]-4-methyl phenol) to cadmium(II) ions. These complexes have been characterized by X-ray crystallography, spectroscopic and analytical techniques. During the formation of 2 and 3, the phenoxido bridging unit of H(3)bemp is transformed to non-bridging modes of binding following the coordination of NO3- and NCS-, while changing one imine function on each ligand to the zwitterionic form, generated through a kind of acid-base reaction for metal ion coordination. The H(3)bemp molecule registers as a highly selective and sensitive fluorescent probe for Cd2+ in a PBS buffer (5 mM in pH = 7.1) at 25 degrees C. in the presence of Cd2+, the increase in fluorescence intensity is accounted for by the formation of [Cd-2(H(2)bemP)(2)](NO3)(2) (1) in solution. The fluorescence quantum yield of H3bemp is 0.201, and it increases more than 4-fold (0.851) in the presence of the cadmium ion. In presence of NCS-, complex 1 showed coordination induced fluorescence enhancement, whereas NO3- and N-3(-) anions quench the emission intensities significantly. (C) 2012 Elsevier Ltd. All rights reserved.