2-(2-(ethylamino)ethyliminomethyl)-4-bromophenol | 1266680-10-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(2-(ethylamino)ethyliminomethyl)-4-bromophenol
• 英文别名: N-ethyl-N-2-aminoethyl-5-bromosalicylaldimine；4-bromo-2-[(2-ethylaminoethylimino)methyl]phenol；4-bromo-2-[2-(ethylamino)ethyliminomethyl]phenol
• CAS: 1266680-10-7
• 化学式: C₁₁H₁₅BrN₂O
• 分子量: 271.157
• InChiKey: PMUJDJKHAADHQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  iron(III) trifluoromethanesulfonate 、 2-(2-(ethylamino)ethyliminomethyl)-4-bromophenol 在 三乙胺 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Fe(III)自旋交叉配合物晶体中热导率和电子自旋态之间的强相关性

  摘要：

  在相变期间改变其热导率的固体可用于开发热开关以控制热流并降低能耗。尽管自旋交叉 (SCO) 配合物的晶体是具有与热传输晶格振动相关的自旋态的代表性固体，但尚未报道 SCO 配合物晶体在自旋态转变期间的热传输特性。在这项工作中，我们报告了单核 Fe( III) SCO 配合物受自旋态跃迁的影响很大。发现热导率在自旋态跃迁开始边缘附近的温度下最小化，声子的速度和平均自由程的乘积也达到了接近自旋态跃迁进行的温度的最小值50%。这些发现表明，在声子的平均自由程最小化到分子间距离的程度的温度下，允许伴随配位键长度延长和振动能量降低的自旋态转变。这些发现还表明，文献中报道的 SCO 配合物是热传输开关材料的有希望的候选者。

  DOI：

  10.1039/d2dt01597h
• 作为产物：
  描述：

  N-乙基乙二胺 、 5-溴水杨醛 以 甲醇 为溶剂， 反应 0.5h， 生成 2-(2-(ethylamino)ethyliminomethyl)-4-bromophenol
  参考文献：
  名称：

  配体场强对5-X-SalEen（X = Me，Br和OMe）基Fe（III）配合物的自旋交叉行为的影响。

  摘要：

  在MeOH中原位制备的Fe（NCS）3与5-X-SalEen配体（5-X-SalEen = 5-取代的水杨醛和N-乙基乙二胺的缩合产物）的反应提供了三种Fe（III）络合物[[Fe（ 5‐X‐SalEen）2 ] NCS；X ＝ Me（1），X ＝ Br（2），X ＝ OMe（3）。所有复合物都显示出相似的结构特征，但磁特性却大不相同。配合物1显示逐渐的自旋交叉，而配合物2和3显示急剧的自旋转变。复数2的T 1/2为237 K，而复数3的T 1/2它的更高值是361K。随着配体取代基的电子给体能力增强，自旋转变温度移向更高的温度。DFT计算已使该实验观察合理化。UV-Vis和循环伏安法研究支持以下事实：配体上的电子密度从Me取代到Br再转化成OMe取代基。为了了解自旋态的变化，已记录了与温度有关的EPR光谱。液体的自旋态平衡已通过Evans NMR光谱法进行了探测，并已对所有配合物的热力学参数进行了评估。

  DOI：

  10.1002/asia.202000156

文献信息

• Solution and solid state properties of Fe(III) complexes bearing N-ethyl-N-(2-aminoethyl)salicylaldiminate ligands
  作者：Paulo N. Martinho、Ana I. Vicente、Sara Realista、Marta S. Saraiva、Ana I. Melato、Paula Brandão、Liliana P. Ferreira、Maria de Deus Carvalho

  DOI：10.1016/j.jorganchem.2013.12.028

  日期：2014.6

  low-spin (LS) state, complex 6 displays a gradual and incomplete spin crossover (SCO) transition over the temperature measured. Solution measurements on a series of six complexes – [Fe(salEen)2]ClO4 (1), [Fe(salEen)2]BPh4·0.5H2O (2), [Fe(5-Br-salEen)2]ClO4 (3), [Fe(5-Br-salEen)2]BPh4·DMF (4), [Fe(3,5-Br-salEen)2]ClO4·EtOH (5) and [Fe(3,5-Br-salEen)2]BPh4·DMF (6) – were performed by UV–vis and NMR spectroscopies

  研究了酚盐环衍生化对在固态和溶液状态下带有N-乙基-N-（2-氨基乙基）水杨酸铝基配体的Fe（III）配合物的磁性的影响。合成了两个新的配合物[Fe（3,5-Br-salEen）2 ] ClO 4 .EtOH（5）和[Fe（3,5-Br-salEen）2 ] BPh 4 .DMF（6）。对这些配合物的SQUID磁力分析研究表明，尽管配合物5处于低旋转（LS）状态，但配合物6显示在所测温度范围内的渐进和不完全自旋交叉（SCO）跃迁。一系列六个配合物的溶液测量– [Fe（salEen）2 ] ClO 4（1），[Fe（salEen）2 ] BPh 4 ·0.5H 2 O（2）， [Fe（5-Br-salEen）2 ] ClO 4（3），[Fe（5-Br-salEen）2 ] BPh 4 ·DMF（4），[Fe（3,5-Br-salEen）2 ] ClO 4 ·EtOH（5）和[Fe（ 3,5-Br-salEen）2
• Thermal Jahn–Teller Distortion Changes and Slow Relaxation of Magnetization in Mn(III) Schiff Base Complexes
  作者：Chantalaksana Chantarangkul、Apinya Patigo、John C. McMurtrie、Rodolphe Clérac、Mathieu Rouzières、Silvia Gómez-Coca、Eliseo Ruiz、Phimphaka Harding、David J. Harding

  DOI：10.1021/acs.inorgchem.4c01317

  日期：2024.7.15

  magnetic properties of four mononuclear Mn(III) complexes is explored in [Mn(salEen-Br)2]Y (salEen-Br = 2-[2-(ethylamino)ethylimino]methyl}-4-Br-phenol; Y = ClO4– 1 and BF4–·1/3CH2Cl2 2) and [Mn(salBzen-Br)2]Y (salBzen-Br = 2-[2-(benzylamino)ethylimino]methyl}-4-Br-phenol; Y = ClO4– 3 and BF4– 4). X-ray structures of [Mn(salEen-Br)2]ClO4·0.45C6H14 1-hexane, [Mn(salEen-Br)2]BF4·0.33CH2Cl2·0.15C6H14 2-dcm-hexane

  [Mn(salEen-Br) 2 ]Y (salEen-Br = 2-[2-(乙氨基)) 中探讨了阴离子和烷基对四种单核 Mn(III) 配合物的电子结构和磁性能的影响)乙基亚氨基]甲基}-4-Br-苯酚；Y = ClO 4 – 1和 BF 4 – ·1/3CH 2 Cl 2 2 ) 和 [Mn(salBzen-Br) 2 ]Y (salBzen-Br = 2- [2-(苄氨基)乙基亚氨基]甲基}-4-Br-苯酚；Y = ClO 4 – 3和 BF 4 – 4 )。 [Mn(salEen-Br) 2 ]ClO 4 ·0.45C 6 H 14 1-己烷、[Mn(salEen-Br) 2 ]BF 4 ·0.33CH 2 Cl 2 ·0.15C 6 H 14 2的X射线结构-dcm-己烷和3 – 4表明它们在环境条件下在单斜P 2 1 / c空间群中结晶。降低温度后， 2-dcm-己烷独特地表现出向单斜P
• Fe(III) salEen derived Schiff base complexes as potential contrast agents
  作者：Bernardo de P. Cardoso、Ana I. Vicente、Joseph B.J. Ward、Pedro J. Sebastião、Fabián Vaca Chávez、Sónia Barroso、Alexandra Carvalho、Stephen J. Keely、Paulo N. Martinho、Maria José Calhorda

  DOI：10.1016/j.ica.2015.04.026

  日期：2015.6

  Three iron(III) complexes with ligands derived from N-ethyl-N-(2-aminoethyl) salicylaldiminate (H, 1; 5-Br, 2; 3-OMe, 3 substituents at the phenyl group) were prepared and the X-ray crystal structures of 1 and 2 are reported. NMR studies of solutions of these complexes in DMSO allowed for investigation of their magnetic behaviour and paramagnetic relaxation contribution. The relaxivities measured ranged from 0.35 to 0.80 mM(-1) s(-1) for proton Larmor frequencies from 0.01 to 300 MHz, in agreement with those known for other iron(III) based contrast agents. Biological studies on colonic epithelial T-84 cell monolayers showed that the compounds exert toxic effects only at concentrations higher than 100 mu M while coincidently reducing colonic epithelial secretory function. These two features make these complexes good candidates for further development in order to be used as MRI contrast agents. (C) 2015 Elsevier B.V. All rights reserved.
• A combined experimental and computational study of supramolecular assemblies in two photoluminescent cadmium(II) complexes with halosalicylaldimine Schiff bases
  作者：Sumit Roy、Antonio Bauzá、Antonio Frontera、Shouvik Chattopadhyay

  DOI：10.1016/j.ica.2016.05.030

  日期：2016.8

  Two new cadmium(II) complexes, [Cd(L-1)(OOCCH3)(OH2)] (1), [Cd-2(L-2)(2)(mu-1,3-SCN)(2)(CH3OH)(2)] (2), have been synthesized using two halosalicylaldimine Schiff bases, HL1 and HL2 where HL1 = 2-(2-(ethylamino) ethyliminomethyl)-4-bromophenol, and HL2 = 2-(2-(dimethylamino) ethyliminomethyl)-4chlorophenol}, respectively. Both complexes have been characterized by elemental and spectral analysis and their structures have been confirmed by single crystal X-ray diffraction studies. Complex 1 is mononuclear and the cadmium(II) centre is apparently coordinated by a tridentate Schiff base, a water molecule and a bidentate chelating acetate. The acetate group could also be thought of as a single entity occupying just one stereochemical site as evident from the small value of chelate bite angle. Complex 2 is dinuclear and contain octahedral cadmium(II) bridged by double end-to-end thiocyanates. Supramolecular interactions in both complexes were also explored. The theoretical study, carried out using density functional theory (DFT) calculations, is devoted to the analysis of the interesting supramolecular assemblies in the solid state of the structures, paying special attention to hydrogen bonding interactions involving the coordinated solvent molecules. (C) 2016 Elsevier B.V. All rights reserved.