1-phenyl-3,8-dimethyl-4,7-diazaundeca-2,8-diene-1,10-dione | 94703-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-phenyl-3,8-dimethyl-4,7-diazaundeca-2,8-diene-1,10-dione
• 英文别名: 4-[2-[(4-oxo-4-phenylbut-2-en-2-yl)amino]ethylamino]pent-3-en-2-one
• CAS: 94703-79-4
• 化学式: C₁₇H₂₂N₂O₂
• 分子量: 286.374
• InChiKey: JICVEAFMMYPWEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-phenyl-3,8-dimethyl-4,7-diazaundeca-2,8-diene-1,10-dione 、 copper hydroxide 以 乙醇 为溶剂， 生成 [Cu(acacphacacen)]
  参考文献：
  名称：

  Influence of the Structure on the Antioxidant Activity of Tetradentate Schiff Bases and their Copper(II) Complexes: Possible Mechanisms

  摘要：

  The influence of the structure on the antioxidant activity of a series of Schiff bases and their copper(II) complexes as well as possible mechanisms of antioxidant activity were investigated. Schiff bases are derived from the condensation of ethane-1,2-diamine or propane-1,2-diamine and pentane-2,4-dione and/or 1-phenylbutane-1,3-dione. The corresponding complexes were synthesized. The antioxidant activity in vitro, determined using reversed-phase thin layer chromatography assay (RP TLC) based on the reaction with 2,2'-diphenyl-1-picrylhydrazyl, was expressed as Trolox equivalent antioxidant capacity (TEAC). The influence of the structure was observed on the basis of interpretable and informative descriptors calculated by hybrid density functional theory (DFT) methods. Structural features responsible for the antioxidant activity of the investigated compounds were discussed. Copper(II) complexes showed a significantly higher antioxidant activity than their corresponding ligands. Calculated quantum-chemical descriptors gave an insight to the reaction mechanism of the scavenging/antioxidant activity of tetradentate Schiff bases and their copper(II) complexes and two different reaction mechanisms were proposed.

  DOI：

  10.5935/0103-5053.20130167
• 作为产物：
  描述：

  乙二胺 、 乙酰丙酮 、 1-苯基-1,3-丁二酮 以 乙醇 为溶剂， 生成 1-phenyl-3,8-dimethyl-4,7-diazaundeca-2,8-diene-1,10-dione
  参考文献：
  名称：

  Influence of the Structure on the Antioxidant Activity of Tetradentate Schiff Bases and their Copper(II) Complexes: Possible Mechanisms

  摘要：

  The influence of the structure on the antioxidant activity of a series of Schiff bases and their copper(II) complexes as well as possible mechanisms of antioxidant activity were investigated. Schiff bases are derived from the condensation of ethane-1,2-diamine or propane-1,2-diamine and pentane-2,4-dione and/or 1-phenylbutane-1,3-dione. The corresponding complexes were synthesized. The antioxidant activity in vitro, determined using reversed-phase thin layer chromatography assay (RP TLC) based on the reaction with 2,2'-diphenyl-1-picrylhydrazyl, was expressed as Trolox equivalent antioxidant capacity (TEAC). The influence of the structure was observed on the basis of interpretable and informative descriptors calculated by hybrid density functional theory (DFT) methods. Structural features responsible for the antioxidant activity of the investigated compounds were discussed. Copper(II) complexes showed a significantly higher antioxidant activity than their corresponding ligands. Calculated quantum-chemical descriptors gave an insight to the reaction mechanism of the scavenging/antioxidant activity of tetradentate Schiff bases and their copper(II) complexes and two different reaction mechanisms were proposed.

  DOI：

  10.5935/0103-5053.20130167

文献信息

• Metal complexes with unsymmetrical tetradentate ketoenamines derived from β-diketones or ethoxymethylene-β-dicarbonyl compounds and 1-amino-4-methyl-3-azahept-4-ene-6-one
  作者：Edmund Kwiatkowski、Marek Kwiatkowski、Aleksandra Olechnowicz

  DOI：10.1016/s0020-1693(00)88047-0

  日期：1984.12

  the synthesis of unsymmetrical ligands and their deuterated derivatives are demonstrated. Using this compound several new unsymmetrical tetradentate ketoenamines, various 9, 10, 11 substituted 4-methyl-5,8-diazaundeca-3,9-diene-2,11-diones and their copper(II), nickel(II) and palladium(II) complexes were obtained. On the basis of the 1H nmr studies the structure of ligands and complexes were established

  显示了戊烷-2,4-二酮和1,2-二氨基乙烷单缩合产物用于不对称配体及其氘代衍生物合成的新制备可能性。使用该化合物，几种新的不对称四齿酮胺，各种9、10、11个取代的4-甲基-5,8-二重氮杂-3,9-二烯-2,11-二酮及其铜（II），镍（II）和钯（II）获得复合物。在1的基础上H nmr研究建立了配体和配合物的结构。1，1，1，1-三氟-4-苯基丁烷-2，4-二酮与戊烷-2，4-二酮和1，2-二氨基乙烷的单缩合反应的产物观察到了意外的立体化学。金属络合物的光谱数据与其平面结构一致。利用双共振技术，配体，镧系元素和溶剂转移试剂的氘化，完成了几乎所有配体和配合物的1 H nmr资源的分配。