4-methyl-2,6-bis(1-(2-pyrrolidinoethyl)iminomethyl)-phenol | 1132774-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-methyl-2,6-bis(1-(2-pyrrolidinoethyl)iminomethyl)-phenol
• 英文别名: 4-Methyl-2,6-bis(2-pyrrolidin-1-ylethyliminomethyl)phenol
• CAS: 1132774-60-7
• 化学式: C₂₁H₃₂N₄O
• 分子量: 356.511
• InChiKey: AKJYNWGTRLYAKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  51.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  zinc(II) chloride dihydrate 、 4-methyl-2,6-bis(1-(2-pyrrolidinoethyl)iminomethyl)-phenol 以 甲醇 为溶剂， 反应 2.0h， 生成 trichloro(4-methyl-2,6-bis(1-(2-pyrrolidinoethyl)iminomethyl)-phenolato)zinc(II)
  参考文献：
  名称：

  Radical Pathway in Catecholase Activity with Zinc-Based Model Complexes of Compartmental Ligands

  摘要：

  Four dinuclear and three mononuclear Zn-II complexes of phenol-based compartmental ligands (HL1-HL7) have been synthesized with the aim to investigate the viability of a radical pathway in catecholase activity. The complexes have been characterized by routine physicochemical studies as well as X-ray single-crystal structure analysis: [Zn-2(H2L1)(OH)(H2O)(NO3)](NO3)(3) (1), [Zn2L2Cl3] (2), [Zn2L3Cl3] (3), [Zn-2(L-4)(2)(CH3COO)(2)] (4), [Zn(HL5)Cl-2] (5), [Zn(HL6)Cl-2] (6), and [Zn(HL7)Cl-2] (7) [L-1-L-3 and L-5-L-7 = 2,6-bis(R-iminomethyl)-4-methylphenolato, where R= N-ethylpiperazine for L-1, R = 2-(N-ethyl)pyridine for L-2, R = N-ethylpyrrolidine for L-3, R = N-methylbenzene for 1,5, R = 2-(N-methyl)thiophene for L-6, R = 2-(N-ethyl)thiophene for L-7, and L-4 = 2-formyl-4-methyl-6-N-methylbenzene-iminomethyl-phenolato]. Catecholase-like activity of the complexes has been investigated in methanol medium by UV-vis spectrophotometric study using 3,5-di-tert-butylcatechol as model substrate. All complexes are highly active in catalyzing the aerobic oxidation of 3,5-di-tert-butylcatechol (3,5-DTBC) to 3,5-di-tert-butylbenzoquinone (3,5-DTBQ). Conversion of 3,5-DTBC to 3,5-DTBQ catalyzed by mononuclear complexes (5-7) is observed to proceed via formation of two enzyme-substrate adducts, ES1 and ES2, detected spectroscopically, a finding reported for the first time in any ZnII complex catalyzed oxidation of catechol. On the other hand, no such enzyme-substrate adduct has been identified, and 3,5-DTBC to 3,5-DTBQ conversion is observed to be catalyzed by the dinuclear complexes (14) very smoothly. EPR experiment suggests generation of radicals in the presence of 3,5-DTBC, and that finding has been strengthened by cyclic voltammetric study. Thus, it may be proposed that the radical pathway is probably responsible for conversion of 3,5-DTBC to 3,5-DTBQ promoted by complexes of redox-innocent Zn-II ion. The ligand-centered radical generation has further been verified by density functional theory calculation.

  DOI：

  10.1021/ic300400v
• 作为产物：
  描述：

  1-(2-氨乙基)吡咯烷 、 2,6-二甲酰-4-甲基苯酚 以 甲醇 为溶剂， 反应 0.5h， 生成 4-methyl-2,6-bis(1-(2-pyrrolidinoethyl)iminomethyl)-phenol
  参考文献：
  名称：

  Mn(ii) complexes of different nuclearity: synthesis, characterization and catecholase-like activity

  摘要：

  通过研究两个“端口”船型席夫碱配体的结构表征的单核、双核和多核Mn（II）配合物，探索了Mn（II）-席夫碱配合物类似于邻苯二酚酶活性的起源。

  DOI：

  10.1039/c5dt03659c

文献信息

• Dinuclear nickel(II) complexes with Schiff base ligands: syntheses, structures and bio-relevant catalytic activities
  作者：Arpita Banerjee、Averi Guha、Pali Maiti、Somen Goswami、Tanmay Chattopadhyay、Tapan Kumar Mondal、Santanu Bhattacharya、Ennio Zangrando、Debasis Das

  DOI：10.1007/s11243-011-9537-4

  日期：2011.11

  Schiff-base ligands, namely [Ni2(L1)(NCS)3(H2O)2], (1) [Ni2(L2)(CH3COO)(NCS)2(H2O)] (2) and [Ni2(L3)(NCS)3] (3), (where L1 = 2,6-bis(N-ethylpyrrolidineiminomethyl)-4-methylphenolato, L2 = 2,6-bis(N-ethylpiperidineiminomethyl)-4-methylphenolato and L3 = 2,6-bisN-ethyl-N-(3-hydroxypropyl iminomethyl)}-4-methylphenolato), have been synthesized and structurally characterized by X-ray single-crystal diffraction

  三种基于甲酚的席夫碱配体的 Ni(II) 配合物，即 [Ni2(L1)(NCS)3(H2O)2]、(1) [Ni2(L2)(CH3COO)(NCS)2( )] (2) 和 [Ni2(L3)(NCS)3] (3)，（其中 L1 = 2,6-双（N-乙基吡咯烷亚氨基甲基）-4-甲基苯酚，L2 = 2,6-双（N-乙基哌啶亚氨基甲基）- 4-methylphenolato 和 L3 = 2,6-bisN-ethyl-N-(3-hydroxypropyl iminomethyl)}-4-methylphenolato)，除了常规的物理化学外，还通过 X 射线单晶衍射进行了合成和结构表征技术。已进行密度泛函理论计算以了解配合物的电子光谱的性质。配合物 1-3 在 50:50 乙腈-水介质中与磷酸 4-硝基苯酯反应促进 O-P 键断裂形成对硝基苯酚并顺利转化 3,5-二-叔丁基邻苯二酚 (3,5-
• Synthesis, characterization and selective fluorescent zinc(II) sensing property of three Schiff-base compounds
  作者：Partha Roy、Koushik Dhara、Mario Manassero、Pradyot Banerjee

  DOI：10.1016/j.ica.2009.01.023

  日期：2009.6

  Three Schiff-base compounds, 4-methyl-2,6-bis(1-(2-piperidinoethyl)iminomethyl)-phenol (HL1), 4-methyl-2,6-bis( 1-(2-pyrrolidinoethyl)-iminomethyl)-phenol (HL2) and (4-methyl-2,6-bis(1-(2- morpholinoethyl) iminomethyl)-phenol) (HL3), have been synthesized and characterized by elemental analysis, FT-IR, H-1 NMR, UV-Vis, electrospray ionisation mass and fluorescence spectroscopy. The emission quantum yield of the compounds increases by ca. 10-17 times by the addition of Zn2+ ion. Introduction of other metal ions of biological and environmental relevance either keeps unaltered or quenches the emission intensity of the ligands. This happens because of large binding constant (similar to 10(4) M-1) of the ligand with Zn2+ ion in acetonitrile. Each of the three ligands forms 1: 2 (ligand: metal) complexes which are characterized by single crystal X-ray diffraction analyses. This imposes rigidity to the ligand due to the complexation and, as a result, the radiative decay constant increases and the corresponding nonradiative decay parameter decreases. All of the ligands react with zinc chloride in acetonitrile to form dinuclear complexes which have been characterized by the elemental analysis, FT-IR, UV-Vis, electrospray ionisation mass spectroscopies and single crystal X-ray structural determinations. (C) 2009 Elsevier B.V. All rights reserved.