N-(2-phenylethyl)-3,5-di-tert-butylsalicylaldimine | 1203602-28-1

• 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: N-(2-phenylethyl)-3,5-di-tert-butylsalicylaldimine
• 英文别名: N-phenylethyl-3,5-di(tert-butyl)-salicylaldimine；HO(C6H2)(t-Bu)2(CHN((CH2)2C6H5))；2,4-Ditert-butyl-6-(2-phenylethyliminomethyl)phenol
• CAS: 1203602-28-1
• 化学式: C₂₃H₃₁NO
• 分子量: 337.505
• InChiKey: IOMKPTIFOUBGCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-phenylethyl)-3,5-di-tert-butylsalicylaldimine 、 copper diacetate 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and X-ray structural characterization of sterically hindered bis(3,5-di-tert-butylsalicylaldiminato)Cu(II) complexes

  摘要：

  Bis(3,5-di-tert-butylsalicylaldiminato)Cu(II) complexes were prepared in high yields from a sterically hindered 3,5-di-tert-butylsalicylaldehyde and a variety of amines using three synthetic approaches. They were all thoroughly characterized by various spectroscopic methods (UV-Vis, IR, EPR and EI-MS). Crystal structures of seven complexes determined by X-ray crystallography show the Cu ion in a N2O2 coordination environment and a tetrahedrally distorted square-planar geometry. The UV-Vis and EPR results indicated that the complexes have the same geometry also in solution. In two solid state structures of the complexes the ligands have obtained an unusual cis-orientation whereas the rest of the complexes are trans-isomers. Computational studies carried out by the density functional theory method verified that in the case of complex with N-alkyl fragment the preferred isomer is trans, while the opposite behavior is observed for the complex with N-phenyl substituent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.03.006
• 作为产物：
  描述：

  3,5-二叔丁基水杨醛 、 2-苯乙胺 以 乙醇 为溶剂， 反应 5.0h， 以98%的产率得到N-(2-phenylethyl)-3,5-di-tert-butylsalicylaldimine
  参考文献：
  名称：

  铜（II）-席夫碱复杂功能化聚丙烯腈纤维，可作为绿色高效的多相催化剂，用于一锅多组分合成1,2,3-三唑和炔丙基胺

  摘要：

  以乙酸铜为铜源，成功制备了一系列以铜为基的席夫碱功能化聚丙烯腈纤维催化剂，并通过元素分析，傅里叶转移红外光谱，紫外可见光谱，X射线光电子能谱和电感耦合等离子体进行了表征。分析。通过扫描电子显微镜，X射线衍射，热重/差示扫描量热分析和机械强度测量，证明了纤维催化剂具有出色的物理强度和热稳定性。此外，这些催化剂已成功应用于单锅多组分铜催化的叠氮化物-炔烃环加成（CuAAC）反应以及醛，炔烃，胺（A3）偶联反应，其中详细研究了不同取代基对纤维催化剂催化活性的影响。其中，bis [N-乙基-3,5-二叔丁基水杨酰亚胺亚胺基铜（II）功能化聚丙烯腈纤维（PAN S2 F-Cu）作为绿色高效催化剂表现出最佳的催化活性，因为它具有高疏水性微环境。将反应物聚集到催化位点并加速反应。此外，PAN S2 F-Cu在按比例放大的实验中表现出色，并具有出色的可回收性（至少十次），这些使其具有进一步应用的巨大潜力。

  DOI：

  10.1002/adsc.201701475
• 作为试剂：
  描述：

  肉桂醇 在 2,2,6,6-四甲基哌啶氧化物 、 N-(2-phenylethyl)-3,5-di-tert-butylsalicylaldimine 、 copper(ll) bromide 作用下， 以 水 为溶剂， 反应 5.0h， 以57%的产率得到肉桂醛
  参考文献：
  名称：

  原位制备的铜（II）配合物在蒸馏水中轻松进行苄醇的露天氧化

  摘要：

  一种高效，选择性和绿色的催化方案，用于通过原位制备的N-异丙基-3,5-二叔丁基水杨醛亚胺（HL 3）–Cu（II）配合物和TEMPO（露天）将伯苄醇露天氧化为醛在此引入2,2,6,6-四甲基-哌啶基氧基）。蒸馏水作为溶剂，反应在80°C的温度下进行，没有任何助剂，例如碱和/或助溶剂。例如，苄醇是最优化的反应条件[80℃，露天，0.3摩尔％的CuBr下定量地和选择性地氧化成苯甲醛在几个小时内2，2摩尔％的HL 3，3 mol％TEMPO和5 mL蒸馏水]。在厌氧条件下，催化剂通过预期的Cu（I）-羟基配合物分解为游离配体和Cu 2 O纳米粒子（直径> 50 nm）。基于这些观察和氘化研究，提出了催化体系的合理反应机理。

  DOI：

  10.1016/j.apcata.2012.09.019

文献信息

• Efficient coupling of CO2 and epoxides with bis(phenoxyiminato) cobalt(III)/Lewis base catalysts
  作者：Ahlam Sibaouih、Paul Ryan、Kirill V. Axenov、Markku R. Sundberg、Markku Leskelä、Timo Repo

  DOI：10.1016/j.molcata.2009.07.009

  日期：2009.10

  A series of unbridged bis(phenoxyiminato) cobalt(III)complexes were synthesized and studied as catalysts for the coupling of CO2 and epoxide. Dimethylamino pyridine (DMAP) and tetrabutyl ammonium bromide (Bu4NBr). were used as co-catalysts in the reaction. Both Co(III)/DMAP and Co(III)/Bu4NBr systems showed high catalytic activity and selectivity in the Coupling of n-hexyl oxide and CO2, resulting in n-hexyl carbonate. Several mono- and di-substituted terminal epoxides were also tested. The reaction mechanism of the Co(III)/DMAP system was investigated in detail using ESI-MS revealing that in addition to the main product, cyclic carbonate, traces of oligomers are formed. (C) 2009 Elsevier B.V. All rights reserved.
• A facile synthesis of mixed ligand Cu(II) complexes with salicylaldehyde and salicylaldimine ligands and their X-ray structural characterization
  作者：Jahir Uddin Ahmad、Minna T. Räisänen、Martin Nieger、Markku Leskelä、Timo Repo

  DOI：10.1016/j.ica.2011.12.009

  日期：2012.4

  High yield synthetic routes to the preparation of new mixed ligand Cu(II) complexes (1-7) derived from a sterically hindered salicylaldimine and the corresponding salicylaldehyde have been developed. The complexes could be obtained either forming a salicylaldimine preligand or two optional Cu(II) complex precursors. One-pot synthesis could also be used. The complexes have been fully characterized by means of elemental analysis, UV-Vis and IR spectroscopy. Crystal structures obtained for four [(3,5-di-tert-butylsalicylaldehydato)(N-R-3,5-di-tert-butylsalicylaldiminato)]Cu(II) (where R = phenyl (1), isopropyl (3), benzyl (5) and 2-phenylethyl (6)) complexes show that three of them are cis-isomers and one is a trans-isomer with respect to the phenolic O-atoms. Complexes 1, 5 and 6 form preferably loose dimers while 3 favors to exist in a loose polymeric structure in a crystal. In all these polynuclear forms the geometry around the Cu(II) ions is a distorted octahedron. (C) 2011 Elsevier B. V. All rights reserved.