N,N'-bis(3-allylsalicylidene)o-phenylenediamine | 206752-24-1

• 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(3-allylsalicylidene)o-phenylenediamine
• 英文别名: 2-[[2-[(2-hydroxy-3-prop-2-enylphenyl)methylideneamino]phenyl]iminomethyl]-6-prop-2-enylphenol
• CAS: 206752-24-1
• 化学式: C₂₆H₂₄N₂O₂
• 分子量: 396.489
• InChiKey: KUVLSRKIUOMCRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 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(3-allylsalicylidene)o-phenylenediamine 、 cobalt(II) chloride 以 neat (no solvent) 为溶剂， 以73%的产率得到N,N'-bis(3-allylsalicylidene)o-phenylenediamine cobalt(II)
  参考文献：
  名称：

  Synthesis of polymer anchored N,N′-bis(3-allyl salicylidene)o-phenylenediamine cobalt(II) Schiff base complex and its catalytic activity for decomposition of hydrogen peroxide

  摘要：

  The anchoring of N,N-bis(3-ally salicylidene)o-phenylenediamine cobalt(II) Schiff base complex on polymer support has been carried out by suspension copolymerization of synthesized N,N'-bis(3-allyl salicylidene)o-phenylenediamine monomer Schiff base (N,N'-BSPDA) with styrene (St) and divinylbenzene (DVB) using azobisisobutyronitrile (AIBN) as initiator in presence of poly(vinyl alcohol). The polymer anchored Schiff base (N,N'-BSPDA) was subsequently loaded with cobalt(II) ions. The cobalt(II) ions loading, degree of cross-linking and swelling in prepared beads have shown dependence on the amount of DVB taken in the reaction mixture. The amount of N,N' -BSPDA monomer Schiff base and its arrangement in cross-linked beads have also shown dependence on the amount of DVB taken in the reaction mixture. The cross-linked beads (Type-III) obtained at 1.50 mmol of DVB have shown highest loading for cobalt(II) ions (1.18 mmol g-(1) of beads) due to maximum amount of N,N'-BSPDA monomer Schiff base on these beads (1.74 mmol g(-1) of beads). The amount of DVB taken in the reaction mixture has shown significant effect on porosity, internal surface area (S-BET), average pore diameter (b) and degree of swelling in prepared beads. The IR, UV and magnetic measurements have provided sufficient evidences for square planar geometry of N,N'-BSPDA cobalt(II) complex both in homogeneous and heterogeneous conditions. The complexation of cobalt(II) ions on polymer anchored N,N' -BSPDA monomer Schiff base has shown a significant increase in its thermal stability. The catalytic activity of polymer supported N,N'-BSPDA cobalt(II) complex was evaluated under different experimental conditions and its activity was compared with unsupported analogue. The energy of activation for decomposition of hydrogen peroxide with supported N,N'-BSPDA cobalt(II) complex has been found to be low (36.04 kJ mol(-1)) in comparison to unsupported one (61.27 kJ mol(-1)). To explain experimental results, a suitable rate expression has been derived. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1381-1169(03)00209-7
• 作为产物：
  描述：

  3-烯丙基-2-羟基苯甲醛 、 邻苯二胺 以 甲苯 为溶剂， 生成 N,N'-bis(3-allylsalicylidene)o-phenylenediamine
  参考文献：
  名称：

  CN116217630

  摘要：

  公开号：

文献信息

• N-Heterocyclic Carbene-Catalyzed Umpolung of Imines for the Enantioselective Synthesis of Dihydroquinoxalines
  作者：Tamal Kanti Das、Avik Ghosh、Kuruva Balanna、Pradipta Behera、Rajesh G. Gonnade、Udaya Kiran Marelli、Abhijit Kumar Das、Akkattu T. Biju

  DOI：10.1021/acscatal.9b00737

  日期：2019.5.3

  N-heterocyclic carbene (NHC) organocatalysis is widely employed for the umpolung of aldehydes and recently to the umpolung of Michael acceptors and aldimines. Described herein is the NHC-organocatalyzed umpolung of aldimines for the enantioselective synthesis of nitrogen heterocycles. The bisimines generated from the condensation of 1,2-phenylenediamines and salicylaldehydes undergo intramolecular

  N-杂环卡宾（NHC）有机催化被广泛用于醛的缩聚，最近被用于迈克尔受体和醛亚胺的缩聚。本文描述了用于对映选择性合成氮杂环的NHC-有机催化的醛亚胺。由1，2-苯二胺和水杨醛缩合生成的双亚胺在手性NHC催化剂的存在下经历分子内环化，从而以中等至良好的收率和er值形成二氢喹喔啉。详尽的DFT研究揭示了-OH基团通过分子内氢键稳定最初生成的aza-Breslow中间体的作用。