N,N'-bis(4-methylsalicylaldehydeimine)ethylenediamine | 89130-15-4

• 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(4-methylsalicylaldehydeimine)ethylenediamine
• 英文别名: bis-(4-methyl-salicylidene)-ethylenediamine；2-[2-[(2-Hydroxy-4-methylphenyl)methylideneamino]ethyliminomethyl]-5-methylphenol
• CAS: 89130-15-4
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: QNRBMRIGKINKHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis(4-methylsalicylaldehydeimine)ethylenediamine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 N,N′-bis(2-hydroxy-4-methylbenzyl)ethylenediamine
  参考文献：
  名称：

  Chemosensor activity of 2-(anthracen-9-yl)-substituted imidazolidines and hexahydropyrimidines

  摘要：

  A number of 2-(anthracen-9-yl)-substituted imidazolidines and hexahydropyrimidines were synthesized by reaction of N,N'-bis[aryl(hetaryl)methyl]ethylene-1,2-diamines and N,N'-bis[aryl(hetaryl)methyl]propane-1,3-diamines with anthracene-9-carbaldehyde. The obtained compounds showed chemosensor activity toward Cd2+, Cu2+, and Hg2+ ions.

  DOI：

  10.1134/s1070428012010162
• 作为产物：
  描述：

  2-羟基-4-甲基苯甲醛 、 乙二胺 以 甲醇 为溶剂， 反应 3.0h， 生成 N,N'-bis(4-methylsalicylaldehydeimine)ethylenediamine
  参考文献：
  名称：

  镍配合物作为四氢吡啶衍生物多组分合成的有效催化剂

  摘要：

  摘要 Ni(Salen)配合物作为一种高效的均相催化剂，在室温下通过芳香醛、芳香胺和β-酮酯在乙醇中的假五组分反应显示出对四氢吡啶衍生物的一锅法合成的催化活性。温和的反应条件、良好的产率、高非对映选择性、操作简单、没有繁琐的分离程序、干净的反应曲线、高原子经济性、廉价的起始材料和环境友好的催化剂是本 MCRs 协议的关键优势。图形概要

  DOI：

  10.1080/00397911.2020.1803357

文献信息

• Influences of polarizability effect of alkyl group and homoring competition effect of substituents on the NMR spectra of salen‐type Schiff base
  作者：Bai‐ying Wei、Chen‐zhong Cao、Chao‐tun Cao

  DOI：10.1002/mrc.5131

  日期：2021.7

  explore the effect of alkyl groups and substituents attached to aromatic ring on the chemical shifts 63 title compounds were synthesized. Their 1 H NMR and 13 C NMR spectra were obtained; and the effects of the alkyl chain length and substituents on the chemical shifts (δH (CH=N), δC (CH=N), δH (OH) and δC (C-OH)) were studied. The results show that: (1) The alkyl polarizability effect index (PEI)

  Salen型席夫碱是一类重要的化合物，应用广泛。为了探索烷基和连接到芳环上的取代基对化学位移的影响，合成了 63 种标题化合物。获得了它们的 1 H NMR 和 13 C NMR 谱图；并研究了烷基链长和取代基对化学位移（δH（CH=N）、δC（CH=N）、δH（OH）和δC（C-OH））的影响。结果表明：（1）烷基极化效应指数（PEI）对上述四个原子的化学位移有重要影响，随着PEI的增加，δH（CH=N）和δc（CH= N)减少，而δH(OH)和δC(C-OH)的值增加。(2)芳环上的取代基X对化学位移的影响与其位置有关，取OH或CH=N为参考。至于取代基对化学位移的影响，哈米特常数σ(X)-OH和激发态取代基参数σ CC ex X - OH以OH为参考的影响与σ(X)-CH= N 和 σ CC ex X - CH = N 以 CH=N 为参照，存在取代基的“同源竞争效应”。(3) X与
• Substituent-Group Effects on the Fluorescence of Aluminum–Schiff Base Complexes and Their Application to the Determination of Aluminum
  作者：Izuo Aoki、Toshiaki Matsunaga、Kunihiro Watanabe

  DOI：10.1246/bcsj.62.2369

  日期：1989.7

  reagents for the SOAP compounds. A methoxyl group at the 4-position of the benzylidene group in the Schiff base and a sulfo group at the 5-position in the amine component increased the fluorescence intensity of the complex. The relationship between the fluorescence intensity and the structure of the complex was investigated by the Free-Wilson method of estimation, and good agreements were obtained

  研究了席夫碱 N-salicylidene-o-aminophenol (SOAP) 中的取代基对其铝配合物荧光的影响。N,N'-二水杨基乙二胺（DSED）衍生物作为醛试剂缩合制备25种不同的SOAP化合物，这些试剂可以方便地水解生成水杨醛衍生物。邻氨基苯酚 (OAP) 衍生物用作 SOAP 化合物的胺试剂。席夫碱中亚苄基4-位的甲氧基和胺组分5-位的磺基增加了配合物的荧光强度。通过 Free-Wilson 估计方法研究了荧光强度与复合物结构之间的关系，并且在荧光强度的实验值和计算值之间获得了良好的一致性。使用 4,4'-二甲基 DSED a 建立了铝的荧光测定程序。
• Effect of Ligand Structure on Ethylene Oligomerization over Salicylaldehyde Imine Nickel Complexes: Experiments and Calculations
  作者：Liduo Chen、Jinyan Tan、Tianyu Lan、Hongliang Huo、Liyuan Sun、Yan Jiang、Na Zhang、Cuiqin Li、Jun Wang

  DOI：10.1002/aoc.7276

  日期：2023.12

  different electron-donating and electron-withdrawing groups on benzene rings were synthesized, using ethylenediamine, salicylaldehyde derivatives with different substituents and nickel chloride hexahydrate as raw materials. Structure characterization, such as elemental analysis, Fourier transform infrared (FT-IR), nuclear magnetic resonance (NMR), ultraviolet–visible (UV–Vis), and electrospray ionization

  以乙二胺、不同取代基的水杨醛衍生物和六水氯化镍为原料，合成了苯环上含有不同给电子基团和吸电子基团的水杨醛亚胺镍配合物Ni1- Ni10 。结构表征，如元素分析、傅里叶变换红外（FT-IR）、核磁共振（NMR）、紫外-可见光（UV-Vis）和电喷雾电离质谱（ESI-MS），证实了合成的结构配合物与理论一致。水杨醛亚胺镍配合物在乙烯齐聚过程中表现出良好的催化活性，且苯环上含有给电子基团的配合物比苯环上含有吸电子基团的配合物具有更高的催化活性。随着酚羟基邻位取代基位阻的增加，催化活性降低，对高碳烯烃的催化选择性也降低。通过密度泛函理论（DFT）计算进一步研究了结构与催化性能的关系，提出了镍配合物催化乙烯齐聚的可能机理。
• A Novel Series of Co^III(salen-type) Complexes Containing a Seven-Membered Metallacycle: Synthesis, Structural Characterization and Factors Affecting the Metallacyclization Rate
  作者：Patrizia Siega、Renata Dreos、Giovanna Brancatelli、Ennio Zangrando、Claudio Tavagnacco、Višnja Vrdoljak、Tomica Hrenar

  DOI：10.1021/om401038v

  日期：2014.2.24

  A series of electronically tuned trans-[Co-III(chel)(CH2Cl)](2) complexes, where chel is a salen derivative (salen = 2,2'-ethylenebis(nitrilomethylidene)-diphenol) containing either two or four methyl substituents in different positions, has been synthesized and characterized, both in solution and in the solid state. These complexes undergo an intramolecular cyclization reaction in methanolic solution to form the corresponding cis beta organometallic derivative containing a seven-membered metallacycle, by replacement of the Cl atom of the axial CH2Cl by the salen phenolate oxygen. The cyclization rate increases on going from two to four methyl substituents in the chelate, in agreement with the electrochemical data that evidence a general shift toward more negative values with an increase in the number of methyl substituents. The cyclization rate is also affected by the substituent position, and both electrochemical and kinetic data evidence a remarkable influence of the methyls on the -C=N- groups of the chelate. The X-ray structures of cyclized complexes, (Co-III(chelCH(2))(py)(H2O)(+), show a dependence of the conformation of the seven-membered metallacycle on the different positions of substituents in the chelate. In fact, in the complex having methyls on the -C=N- groups, the conformation is characterized by having the methylene carbon atom significantly displaced (ca. 1.26 angstrom) from the aromatic ring plane, whereas in the complex lacking methyl groups in those positions, the atoms of the Ph-O-CH2 fragment are coplanar. The standard Gibbs energies obtained by quantum chemical calculation reveal that the different conformations observed in the solid state are mainly the result of the energetically unfavorable setup of the methyls on the -C=N- groups and of the energetically favorable displacement of the CH2 group out of plane of the aromatic ring. H-1 NMR data suggest that the different conformations of the metallacycle are, at least partially, retained in solution.
• Diehl, H.; Liggett, L. M.; Harrison, G. C., Iowa State College Journal of Science, 1947, vol. 22, p. 91 - 109
  作者：Diehl, H.、Liggett, L. M.、Harrison, G. C.、Hach, C. C.、Curtis, R.

  DOI：——

  日期：——