4,6-bis(tert-butyl)-2-((benzyl)iminomethyl)phenol | 97746-38-8

• 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: 4,6-bis(tert-butyl)-2-((benzyl)iminomethyl)phenol
• 英文别名: [(tBu)ON(Bn)]H；2-(Benzyliminomethyl)-4,6-ditert-butylphenol；2-(benzyliminomethyl)-4,6-ditert-butylphenol
• CAS: 97746-38-8
• 化学式: C₂₂H₂₉NO
• 分子量: 323.478
• InChiKey: LWCLQZJBKSAXHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  4,6-bis(tert-butyl)-2-((benzyl)iminomethyl)phenol 、 copper diacetate 以 甲醇 为溶剂， 生成 bis(N-benzyl-3,5-ditert-butylsalicylaldiminato)copper(II)
  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 、 苄胺 生成 4,6-bis(tert-butyl)-2-((benzyl)iminomethyl)phenol
  参考文献：
  名称：

  ε-己内酯开环聚合中含席夫碱的铝配合物的改进：五元环系统

  摘要：

  合成了一系列带有席夫碱的五元环和六元环的铝配合物，并研究了它们在ε-己内酯（CL）的开环聚合中的应用。已显示五元环Al络合物的聚合速率明显高于六元环Al络合物（CL聚合的2至3倍）。X射线数据表明，与六元环Al络合物相比，五元环Al络合物的Al中心离席夫碱配体更远。密度泛函理论计算的结果还表明，五元环Al配合物的Al中心周围有更多空间可以减少CL聚合中的空间排斥，并提高五元环Al配合物的催化活性。

  DOI：

  10.1021/acs.organomet.7b00068
• 作为试剂：
  描述：

  糠醛 在 tetrachlorobis(tetrahydrofuran)titanium(IV) 、 4,6-bis(tert-butyl)-2-((benzyl)iminomethyl)phenol 锰 、 三甲基氯硅烷 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 meso-1,2-di(2'-furyl)ethane-1,2-diol 、 1,2-di(furan-2-yl)ethane-1,2-diol
  参考文献：
  名称：

  Highly diastereoselective pinacol coupling of aldehydes catalyzed by titanium-Schiff base complexes

  摘要：

  A new effective methodology for a highly diastereoselective pinacol coupling of aldehydes is described. The method employes 3 mol % of a complex prepared in situ from TiCl4(THF)(2) and a Schiff base in acetonitrile. The catalytic cycle is realized with Me3SiCl and Mn as reducing agent. The dependence of the diastereoselectivity on the Schiff base used is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00100-8

文献信息

• Bidentate salicylaldiminato tin(ii) complexes and their use as lactide polymerisation initiators
  作者：Nonsee Nimitsiriwat、Vernon C. Gibson、Edward L. Marshall、Mark R. J. Elsegood

  DOI：10.1039/b812877d

  日期：——

  A study of the reactions of several salicylaldimines (ortho-iminophenols) with Sn(NMe2)2 reveals that the sterics and electronics of the N-substituent play a principal role in determining the product mixture. Thus mono(chelate) tin(II) amides have only been isolated with bulky N-anilido substituents, including [2,4-X2-6-CHN-2,6-iPr2C6H3}-C6H2O]Sn(-NMe2)]2, X = Cl, 1; X = I, 2 and [2,4-Cl2-6-CHN-2

  对几种水杨醛亚胺（邻亚氨基苯酚）与Sn（NMe2）2的反应的研究表明，N-取代基的空间和电子学在确定产物混合物中起主要作用。因此，单（螯合物）锡（II）酰胺仅用大的N-苯胺基取代基分离，包括[2,4-X2-6- CHN-2,6-iPr2C6H3} -C6H2O] Sn（-NMe2）] 2 ，X = Cl，1; X = I，2和[2,4-Cl2-6- CHN-2,4,6-tBu3C6H2} -C6H2O] Sn（NMe2），3。具有较小的N-芳基和N-烷基取代的水杨醛亚胺，的混合物即使酚盐环带有大的叔丁基取代基，也会形成单螯合物和双螯合物。此外，当苯胺基基团带有吸电子取代基时，亚氨基碳被活化而趋向亲核攻击（如[2,4-tBu2-6- CH（NMe2）N-2,4,6-Br3C6H2的形成所证明} -C6H2O] Sn，4）；当卤素取代基位于酚环上时，没有观察到这样的反应性。还研究了配合物
• Synthesis, structural determination, and ethylene polymerization chemistry of mono(salicylaldiminato) complexes of titanium(IV)
  作者：David Owiny、Sean Parkin、Folami T Ladipo

  DOI：10.1016/s0022-328x(03)00454-6

  日期：2003.7

  Titanium(IV)mono(salicylaldiminato) complexes [L1Ti(NMe2)3] (1) and [L1TiCl3] (2) have been synthesized by treatment of Ti(NMe2)4 or TiCl4 with one equivalent of [4,6-Bu2t-2-(CHNBut)C6H3OH] (L1H) or [4,6-Bu2t-2-(CHNBut)C6H3OSiMe3] (L1SiMe3), respectively. The compounds are monomeric in solution and in the solid-state. Reactions of TiCl4 with one equivalent of [4,6-Bu2t-2-(CHNCH2Ph)C6H3OH] (L2H)

  通过用一当量的Ti（NMe 2）4或TiCl 4处理，合成了钛（IV）单（水杨基铝二氨基）络合物[L 1 Ti（NMe 2）3 ]（1）和[L 1 TiCl 3 ]（2）。[4,6-卜2吨-2-（CHNBu吨）C 6 H ^ 3 OH]（大号1 ħ）或[4,6-卜2吨-2-（CHNBu吨）C 6 ħ 3 OSiMe 3 ]（L 1SiMe 3）。这些化合物在溶液中和处于固态时均为单体。TiCl 4与一当量的[4,6-Bu 2 t -2-（CH = NCH 2 Ph）C 6 H 3 OH]（L 2 H）和[4,6-Bu 2 t -2- CHN（2-C 6 H 4 OH）} C 6 H 3 OH]（L 3 H 2）生成[L 2 TiCl 2（μ-Cl）] 2（3）和[L 3 TiCl 2 ]分别为2（4）。当将4在THF中搅拌16小时时，也以定量收率生产了[L 3 TiCl 2（THF）]（5）。TiCl
• 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.
• Improvement in Aluminum Complexes Bearing Schiff Bases in Ring-Opening Polymerization of ε-Caprolactone: A Five-Membered-Ring System
  作者：Chieh-Ling Lee、Ya-Fan Lin、Man-Ting Jiang、Wei-Yi Lu、Jaya Kishore Vandavasi、Li-Fang Wang、Yi-Chun Lai、Michael Y. Chiang、Hsuan-Ying Chen

  DOI：10.1021/acs.organomet.7b00068

  日期：2017.5.22

  series of five- and six-membered-ring Al complexes bearing Schiff bases was synthesized and their application to the ring-opening polymerization of ε-caprolactone (CL) was studied. The five-membered-ring Al complexes have been shown to have a significantly higher polymerization rate than six-membered-ring Al complexes (2–3 fold for CL polymerization). The X-ray data revealed that the Al center of a five-membered-ring

  合成了一系列带有席夫碱的五元环和六元环的铝配合物，并研究了它们在ε-己内酯（CL）的开环聚合中的应用。已显示五元环Al络合物的聚合速率明显高于六元环Al络合物（CL聚合的2至3倍）。X射线数据表明，与六元环Al络合物相比，五元环Al络合物的Al中心离席夫碱配体更远。密度泛函理论计算的结果还表明，五元环Al配合物的Al中心周围有更多空间可以减少CL聚合中的空间排斥，并提高五元环Al配合物的催化活性。
• Synthesis and X-ray structural characterization of sterically hindered bis(3,5-di-tert-butylsalicylaldiminato)Cu(II) complexes
  作者：Jahir Uddin Ahmad、Minna T. Räisänen、Martin Nieger、Markku R. Sundberg、Pawel J. Figiel、Markku Leskelä、Timo Repo

  DOI：10.1016/j.poly.2012.03.006

  日期：2012.5

  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.