N,N’-bis{1-(2-hydroxyphenyl)-ethylidene}-2-hydroxy-1,3-propanediamine | 150922-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,N’-bis{1-(2-hydroxyphenyl)-ethylidene}-2-hydroxy-1,3-propanediamine
• 英文别名: [2-hydroxy-(1,3-diiminopropyl)2,2’-methyl]bisphenol；N,N′-(2-hydroxypropane-1,3-diyl)bis(2-hydroxyacetophenimine)；2-hydroxyacetophenone-(1,3-diamino-2-hydroxypropane)；bis(orthohydroxyacetophenone)propylene(2-hydroxy)diimine；2-[N-[2-hydroxy-3-[1-(2-hydroxyphenyl)ethylideneamino]propyl]-C-methylcarbonimidoyl]phenol
• CAS: 150922-01-3
• 化学式: C₁₉H₂₂N₂O₃
• 分子量: 326.395
• InChiKey: SIKPJMLZPNOXGB-UHFFFAOYSA-N

物化性质

• 沸点：
  478.0±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  N,N’-bis{1-(2-hydroxyphenyl)-ethylidene}-2-hydroxy-1,3-propanediamine 、 bis(acetylacetonate)oxovanadium 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以73%的产率得到[V^VO((2-hydroxyacetophenone-(1,3-diamino-2-hydroxypropane)))]
  参考文献：
  名称：

  Synthesis, structural characterization, encapsulation in zeolite Y and catalytic activity of an oxidovanadium(V) complex with a tribasic pentadentate ligand

  摘要：

  Reaction of [(VO)-O-IV(acac)(2)] with H(3)hap-dahp (I: Schiff base derived from 2-hydroxyacetophenone and 1,3-diamino-2-hydroxypropane) in methanol under aerobic conditions resulted in the formation of the complex [(VO)-O-V(hap-dahp)] (1). Treatment of I with vanadium(IV) exchanged zeolite Y followed by aerial oxidation gave the encapsulated oxidovanadium(V) complex [(VO)-O-V(hap-dahp)]-Y (2) in the nanocavity of zeolite Y. Elemental analysis, spectroscopic (IR, electronic, H-1 and V-51 NMR) studies, scanning electron micrographs and X-ray diffraction patterns have been used to characterize these complexes, which have a distorted octahedral structure, confirming the tribasic O3N2 binding mode of the ligand. The encapsulated complex [(VO)-O-V(hap-dahp)]-Y (2) catalyzes the oxidation of styrene, methyl phenyl sulfide and diphenyl sulfide using H2O2 as an oxidant in good yield (82%, 98% and 81%, respectively). Styrene, under optimized reaction conditions, gave five reaction products, namely styrene oxide, benzaldehyde, 1-phenylethane-1,2-diol, benzoic acid and phenylacetaldehyde, while the organic sulfides gave the corresponding sulfoxides as the major product. The neat complex [(VO)-O-V(hap-dahp)] (1) also exhibits good catalytic activity for these substrates. The encapsulated complex showed a good recycling ability. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.02.036
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 1,3-二氨基-2-羟基丙烷 以 甲醇 为溶剂， 生成 N,N’-bis{1-(2-hydroxyphenyl)-ethylidene}-2-hydroxy-1,3-propanediamine
  参考文献：
  名称：

  合成，晶体结构，磁性能和一个不寻常的双核的DFT计算μ 2 -alkoxido桥接铁（III）络合物†

  摘要：

  一种新的双核二（μ-烷氧基）桥接复合物[Fe 2 L 2 ]（1）（H 3 L =N，N'-双{1-（2-（羟基苯苯基）-亚乙基} -2-羟基-1,3-丙二胺）已被合成和表征。1的结构由一个中心对称的二聚体组成，其中两个晶体学上等价的金属离子被两个烷氧基氧原子不对称桥连。在该结构中，每个配体均协调至一个Fe（III）中心，因此亚氨基氮原子处于顺式位置，这对该配体而言非常罕见。配合物的可变温度磁化率测量结果表明，两个铁（III）中心是反铁磁耦合的（J = -17.46 cm -1）。已经通过DFT计算研究了交换机制。此外，理论研究还被用于合理化席夫碱配体的异常配位模式。此外，还从理论上分析了固态结构中存在的弱力或溶剂分子对构象变化的影响。此理论计算包含两个以上相似的结构，的[Fe 2大号' 2 ]·CH 2氯2（2）和的[Fe 2 L' 2 ]·2CH 3 CN（3）（H 3 L'= Ñ，Ñ``-双（水杨基）-1

  DOI：

  10.1039/c3dt51153g

文献信息

• Silylation coupled with desilylation as a route to newer syntheses
  作者：Kamalendu Dey、Kartik Kumar Nandi、George B. Kauffman

  DOI：10.1016/s0277-5387(00)83488-9

  日期：1994.7

  a new series of bimetallic oxovanadium(IV), organotitanium(IV) and organotin(IV) compounds. The reaction of [(π-C5H5)2Ti]2Cl(salphd) (5), synthesized in this study, with Ph2CNSiMe3 is also described. The complexes have been characterized by elemental analyses, molar conductance values, magnetic susceptibilities, molecular weights and spectroscopic (UV-visible, IR, 1H NMR, and ESR) data.

  摘要将Schiff碱双（水杨醛）丙烯（2-羟基）二亚胺（缩写为H3salphd）和双（邻羟基苯乙酮）丙烯（2-羟基）二亚胺（缩写为H3ohaphd）进行三甲基甲硅烷基化反应，得到三甲基甲硅烷基化的（Me3Silylated）3Silylated配体和Me3Si3Si）3ohaphd。这些新的甲硅烷基化的配体与VOCl2·2H2O，（π-C5H5）2TiCl2和（CH3）2SnCl2平稳反应，生成了一系列新的双金属氧钒（IV），有机钛（IV）和有机锡（IV）化合物。还描述了本研究中合成的[（π- ）2Ti] 2Cl（salphd）（5）与Ph2CNSiMe3的反应。通过元素分析，摩尔电导值，磁化率，分子量和光谱数据（紫外可见光，IR，1H NMR和ESR）表征了配合物。
• Oxidative Cleavage of DNA by Transition Metal Complexes: Synthesis, Spectral Characterization and DNA Interactions of Copper(II) Complexes with Quinquedentate Schiff Base Ligands
  作者：M. Pragathi、K. Hussain Reddy

  DOI：10.14233/ajchem.2019.21558

  日期：——

  Designing of dinucleating ligands, with an additional donor atom that can bridge two metals in a more or less fixed geometry has rapidly developed in recent years. Part of the interest stems from the fact that the corresponding complexes are often studied as enzyme mimics. Two quinquedentate ligands have been synthesized by condensing salicylaldehyde/o-hydroxy- acetophenone with 2-hydroxy-1,3- propanediamine. The ligands and their metal complexes are synthesized and characterized by physicochemical and spectral analysis. Electrochemical behaviour of the complexes is investigated through cyclic voltammetric studies. E1/2 values are observed at 0.360 and 0.331 V vs. Ag/AgCl for the complexes. The non-equivalent current in cathodic and anodic peaks (ic/ia = 1.224 and 1.065 at 100 mV s-1) for metal complexes indicate quasi-reversible behaviour. Binding interactions of the dinuclear copper(II) complexes with calf thymus DNA are investigated using absorption spectrophotometry. Cleavage activities of these complexes are uncovered on a double stranded pBR plasmid DNA by using gel electrophoresis experiments in different conditions. At micromolar concentration, the ligands exhibit no significant activity, whereas the metal complexes show significantly enhanced nuclease activity due to the presence of metal ions. Copper complexes cleave DNA more effectively in the presence of oxidant. This is consistent with the increased production of hydroxyl radicals by cuprous ions similar to the well known “Fenton reaction”.

  近年来，设计具有额外配体原子的双金属配体，以在一定的几何形状下桥接两种金属的研究迅速发展。这部分兴趣源于相关的配合物通常作为酶的模拟物进行研究。通过将水杨醛/邻羟基乙酮与2-羟基-1,3-丙二胺缩合合成了两种五齿配体。对这些配体及其金属配合物进行了合成和物理化学及光谱分析表征。通过循环伏安法研究了配合物的电化学行为。配合物的E1/2值在相对于Ag/AgCl的0.360和0.331 V处被观察到。在100 mV/s的扫描速率下，金属配合物在阴极和阳极峰的非等效电流（ic/ia = 1.224和1.065）表明其呈现准可逆行为。采用吸收光谱法研究了双核铜(II)配合物与小牛胸腺DNA的结合相互作用。通过在不同条件下进行凝胶电泳实验，揭示了这些配合物在双链pBR质粒DNA上的 cleavage 活性。在微摩尔浓度下，配体显示出无显著活性，而金属配合物由于金属离子的存在显示出显著增强的核酸酶活性。在存在氧化剂的情况下，铜配合物对DNA的 cleave 效果更加显著。这与亚铜离子增加羟基自由基的产生一致，类似于著名的“芬顿反应”。
• Isolation of four new CoII/CoIII and NiII complexes with a pentadentate Schiff base ligand: syntheses, structural descriptions and magnetic studies
  作者：Sambuddha Banerjee、Madhusudan Nandy、Soma Sen、Sandip Mandal、Georgina M. Rosair、Alexandra M. Z. Slawin、Carlos J. Gómez García、Juan M. Clemente-Juan、Ennio Zangrando、Nicol Guidolin、Samiran Mitra

  DOI：10.1039/c0dt00923g

  日期：——

  assigned a tentative mononuclear structure based on IR, UV-Vis spectroscopic, 1H-NMR and ESI mass study results and is supposed to have one NiII center coordinated with a ligand fragment in square planar geometry. The variable temperature magnetic susceptibility study for 2 and 4 is performed which indicate for both 2 and 4 the presence of intracluster dominant ferromagnetic interactions.

  在本文中，我们报告了四种新的Co II / Co III和Ni II配合物与温度和pH值的依赖关系，这些配合物具有五齿Schiff碱配体H 3 L ，该配合物通过缩合1,3，-二氨基丙-2-醇与2-羟基苯乙酮以1：2的摩尔比。室温合成涉及Co II和Ni II硝酸盐和配体H 3 L导致分离出双核物质[Co 2 L 2（H 2 O）]（1）和单核络合物[Ni（LH）]。 （3），分别，而在碱性pH引线回流到四核配合物，[CO II 2钴III 2大号2（μ 3 -OMe）2（NO 3）（H 2 O）2 ] NO 3 ·2（H 2 O）（2）和[镍4大号2（μ 3 -OMe）2（H 2 O）2 ]·2H 2 O（4）。1被发现是一个简单的单烷氧-bridged钴III双核物种，而2和4都是类菱形双氧桥的四聚体复合物和μ 3座-methoxo桥梁，从甲醇溶剂衍生的，在开放dicubane布置。此外2显示了六个坐标有序的Co
• Dey, Kamalendu; Bhaumik, Bijali Bikash; Sarkar, Saikat, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2004, vol. 43, # 4, p. 773 - 777
  作者：Dey, Kamalendu、Bhaumik, Bijali Bikash、Sarkar, Saikat

  DOI：——

  日期：——