2,4-di-tert-butyl-6-(2,6-diisopropylphenyliminomethyl)phenol | 210882-24-9

• 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: 2,4-di-tert-butyl-6-(2,6-diisopropylphenyliminomethyl)phenol
• 英文别名: 2,4-Ditert-butyl-6-[[2,6-di(propan-2-yl)phenyl]iminomethyl]phenol
• CAS: 210882-24-9
• 化学式: C₂₇H₃₉NO
• 分子量: 393.613
• InChiKey: GDSXBTWQPNERCY-UHFFFAOYSA-N

物化性质

• 熔点：
  79-81 °C
• 沸点：
  506.6±50.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  2,4-di-tert-butyl-6-(2,6-diisopropylphenyliminomethyl)phenol 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 2-[(2,6-diisopropylphenylamino)methyl]-4,6-di-tert-butylphenol
  参考文献：
  名称：

  单阴离子和二阴离子氨基酚盐双齿配体支持的有机铝配合物的结构多样性和多功能性

  摘要：

  本贡献描述了由各种取代的氨基酚盐型配体支持的结构多样的有机铝物质的合成和结构表征：这些Al络合物均源自AlMe 3与氨基酚2-CH 2 NH（R）-C 6 H 3的反应OH（1a，R =均三甲苯（Mes）; 1b，R = 2,6-二异丙基苯基（Diip））和2-CH 2 NH（R）-4,6- t Bu 2 -C 6 H 2 OH（1c，R = Mes；1d，R = Diip）。AlMe 3与1a的低温反应- b容易得到相应的Al二聚体种类[μ-η 1，η 1 -N，O- {2-CH 2 NH（R）-C 6 H ^ 4 ö}] 2的Al 2我4（图2a - b），由12元环aluminacycles具有两个μ-η 1，η 1 - N，O -aminophenolate单元，如通过X射线晶体学研究测定。加热的甲苯溶液2a中（80℃，3小时），得到双核铝的定量和直接形成复合体A1 [η 2 -N;

  DOI：

  10.1016/j.jorganchem.2011.09.020
• 作为产物：
  描述：

  3,5-二叔丁基水杨醛 、 2,6-二异丙基苯胺 在 甲酸 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以61%的产率得到2,4-di-tert-butyl-6-(2,6-diisopropylphenyliminomethyl)phenol
  参考文献：
  名称：

  Synthesis and characterisation of neutral dialkylaluminium complexes stabilised by salicylaldiminato ligands, and their conversion to monoalkylaluminium cations †

  摘要：

  将水杨醛亚胺配体3,5-But2-2-(OH)C6H2CHNR [R = 2,6-Me2C6H3 (1a), 2,6-Pri2C6H3 (1b), 3,5-(CF3)2C6H3 (1c), 4-(NO2)C6H4 (1d), 4-ClC6H4 (1e), 1-萘基 (1f), But (1g)]与甲苯中的Me3Al反应，经后处理得到高度结晶（除2c为油状物外）的配合物{3,5-But2-2-(O)C6H2CHNR}AlMe2 [R = 2,6-Me2C6H3 (2a), 2,6-Pri2C6H3 (2b), 3,5-(CF3)2C6H3 (2c), 4-(NO2)C6H4 (2d), 4-ClC6H4 (2e), 1-萘基 (2f), But (2g)]。在这些体系中加入THF并反应B(C6F5)3，顺利得到[{3,5-But2-2-(O)C6H2CHNR}AlMe(THF)]+ [R = 2,6-Me2C6H3 (3a), 2,6-Pri2C6H3 (3b), 3,5-(CF3)2C6H3 (3c), 4-(NO2)C6H4 (3d), 4-ClC6H4 (3e), 1-萘基 (3f), But (3g)]，即B(C6F5)3Me−盐。相比之下，在没有THF的二氯甲烷溶液中进行相同的反应得到复杂的混合物：从2g与B(C6F5)3在CD2Cl2中的反应获得的产品混合物的NMR谱表明，其中存在{3,5-But2-2-(O)C6H2CHNBut}AlMe(C6F5)]和B(C6F5)2Me。化合物2a和2b已通过单晶X射线结构确定法表征，并显示出几乎相同的构象。在这两个体系中，铝中心的四面体几何结构都存在明显的畸变。

  DOI：

  10.1039/b100743m

文献信息

• The use of Cu and Zn salicylaldimine complexes as catalyst precursors in ring opening polymerization of lactides: ligand effects on polymer characteristics
  作者：Suraj Bhunora、Jane Mugo、Archana Bhaw-Luximon、Selwyn Mapolie、Juanita Van Wyk、James Darkwa、Ebbe Nordlander

  DOI：10.1002/aoc.1728

  日期：2011.2

  copper (II) and zinc (II) complexes based on N,O‐bidentate salicylaldimine Schiff base ligands has been synthesized and characterized using various spectroscopic techniques. These complexes were then evaluated as initiators in ring‐opening polymerization of lactides at both 70 °C and 110 °C. The effect of structural changes in the complexes on the ability of these compounds to initiate lactide polymerization

  基于各种N，O-二齿水杨基亚胺席夫碱配体的一系列单体四配位铜（II）和锌（II）配合物已被合成并使用各种光谱技术进行了表征。然后在70°C和110°C下，评估这些络合物作为丙交酯开环聚合反应的引发剂。配合物的结构变化对这些化合物引发丙交酯聚合能力的影响以及对所得聚合物的化学和物理特性的影响表明，金属配合物的配位几何结构MSchiff碱配体上的O键长度和取代基均在催化剂活性中起作用。在铜配合物中，电子因素占主导地位，而在锌引发剂中，空间因素占主导地位。Zn和Cu络合物均显示活性环开环聚合的特征。版权所有©2010 John Wiley＆Sons，Ltd.
• Dimethylaluminium aldiminophenolates: synthesis, characterization and ring-opening polymerization behavior towards lactides
  作者：Wenjuan Zhang、Youhong Wang、Wen-Hua Sun、Lin Wang、Carl Redshaw

  DOI：10.1039/c2dt31215h

  日期：——

  The stoichiometric reaction of the salicylaldimine derivatives (L1–L12) with trimethylaluminium afforded the corresponding dimethylaluminium aldiminophenolates (C1–C12), which were fully characterized by NMR spectroscopy and elemental analysis. The molecular structures of the representative complexes C1, C6, and C8 were determined by the single-crystal X-ray diffraction, which revealed distorted tetrahedral geometry at aluminium. Activation of the dimethylaluminium aldiminophenolates for the ring-opening polymerization required one equivalent of BnOH. On the basis of the polymerization results for L-lactide, D-lactide or rac-lactide, higher efficiency was observed for the ROP of D-lactide, and the nature of the ligands present significantly affected the observed catalytic activities and the properties of the resultant polylactides.

  水杨醛亚胺衍生物（L1–L12）与三甲基铝的化学计量反应生成相应的二甲基铝醛亚宝系（C1–C12），这些化合物通过核磁共振光谱和元素分析进行了充分表征。代表性络合物C1、C6和C8的分子结构通过单晶X射线衍射确定，显示出铝呈扭曲的四面体几何结构。激活二甲基铝醛亚宝系用于开环聚合需要一个当量的BnOH。根据L-乳酸、D-乳酸或外消旋乳酸的聚合结果，D-乳酸的开环聚合效率较高，并且配体的性质显著影响了观察到的催化活性以及所得到的聚乳酸的性质。
• The Synthesis of Copper(II) Salicylaldiminato Complexes and their Catalytic Activity in the Hydroxylation of Phenol
  作者：Juanita L. van Wyk、Selwyn Mapolie、Anders Lennartson、Mikael Håkansson、Susan Jagner

  DOI：10.1515/znb-2007-0305

  日期：2007.3.1

  The synthesis of copper(II) salicylaldiminato complexes and their application in the catalytic hydroxylation of phenol is reported. Tetracoordinated copper complexes (Cu(Lⁿ)₂) were obtained by reacting the N-phenylsalicylaldimine ligands (HL¹ -HL⁷) with copper acetate in a 2 : 1 mole ratio. The reaction of N-(2,6-diisopropyl)phenyl-3,5-di-tert-butylsalicylaldimine (HL⁷) with copper acetate in a 1 : 1 mole ratio afforded a dinuclear complex, which was not obtained with the other ligand systems. All complexes were characterized using FT-IR and elemental analysis. X-Ray crystal structures of complexes 2, 5 and 8 have also been obtained. The catalytic activity of these complexes was evaluated in the hydroxylation of phenol using oxygen and hydrogen peroxide as co-oxidants in aqueous media in the pH range 3 - 6. All complexes studied were found to be active for the hydroxylation process over the pH range studied with higher selectivity for catechol formation.

  报道了铜(II)水杨醛亚胺配合物的合成及其在苯酚催化羟基化中的应用。通过将N-苯基水杨醛亚胺配体（HL^1-HL^7）与乙酸铜按2：1的摩尔比反应得到了四配位铜配合物（Cu(L^n)_2）。N-(2,6-二异丙基)苯基-3,5-二叔丁基水杨醛亚胺（HL^7）与乙酸铜按1：1的摩尔比反应得到了一个双核复合物，而其他配体系统未能得到这种复合物。所有配合物均通过傅里叶变换红外光谱和元素分析进行了表征。复合物2、5和8的X射线晶体结构也已得到。这些配合物在pH值为3-6的水介质中使用氧气和过氧化氢作为共氧化剂对苯酚进行羟基化反应的催化活性得到了评估。研究的所有配合物在所研究的pH范围内均被发现对羟基化过程具有活性，对邻苯二酚的形成具有较高的选择性。
• Vanadium(<scp>iii</scp>) phenoxyimine complexes for ethylene or ε-caprolactone polymerization: mononuclear versus binuclear pre-catalysts
  作者：Lucy Clowes、Mark Walton、Carl Redshaw、Yimin Chao、Alex Walton、Pertti Elo、Victor Sumerin、David L. Hughes

  DOI：10.1039/c2cy20571h

  日期：——

  The mononuclear [C6H4NCH(ArO)]2VCl(THF)} (Ar = 2,4-t-Bu2C6H2 (1), Ar = C6H4 (2)), O[C6H4NCH(ArO)]2}VCl(THF) (Ar = 2,4-t-Bu2C6H2 (3), Ar = C6H4 (4)) and the binuclear vanadium(III) complexes [C6H4NCH(ArO)]VCl2(THF)2}2(μ-CH2CH2) (Ar = 2,4-t-Bu2C6H2 (5), Ar = C6H4 (6)), have been synthesized and fully characterized. The compounds [C6H5NCH(ArO)]VCl2(THF)2 (Ar = 2,4-t-Bu2C6H2 (7), Ar = C6H4 (8)), [2,4,6-Me3–C6H2NCH(ArO)]VCl2 (Ar = 2,4-t-Bu2C6H2 (9), Ar = C6H4 (10)) and [2,6-i-Pr2-C6H3NCH(ArO)]VCl2(THF)2 (Ar = 2,4-t-Bu2C6H2 (11), Ar = C6H4 (12)), μ-CH2CH2[NCH(C6H4O)]2VCl(THF)} (14) and C6H4[NCH(C6H4O)]2VCl(THF)} (15) were synthesized for comparative polymerization studies. The dizwitterionic compound [2,6-i-Pr2-C6H3N+(H)CH(C6H4O)]2VCl2O (13) was also isolated, and presumably formed via a fortuitous hydrolysis reaction. The complexes 2, 5 and 13 have been structurally characterized; the molecular structure of the parent ligand (L5) in 5 is also reported. All complexes have been screened for ethylene as well as ε-caprolactone polymerization, and results are compared against those for known related mono- and bi-nuclear counterparts to evaluate for possible cooperative effects. The compounds 10 and 12 have been supported on modified SiO2, analysed by XPS and subjected to homo-polymerization (ethylene) and co-polymerization (1-hexene and ethylene) studies.

  合成并全面表征了单核化合物[ NCH(ArO)]2VCl(THF)} (Ar = 2,4-t-Bu2C6H2 (1)，Ar = C6H4 (2))和O[ NCH(ArO)]2}VCl(THF) (Ar = 2,4-t-Bu2C6H2 (3)，Ar = (4))，以及双核钒(III)络合物[ NCH(ArO)]VCl2(THF)2}2(μ-CH2CH2) (Ar = 2,4-t-Bu2C6H2 (5)，Ar = (6))。合成了化合物[C6H5NCH(ArO)]VCl2(THF)2 (Ar = 2,4-t-Bu2C6H2 (7)，Ar = (8))、[2,4,6-Me3–C6H2NCH(ArO)]VCl2 (Ar = 2,4-t-Bu2C6H2 (9)，Ar = (10))和[2,6-i-Pr2- CH(ArO)]VCl2(THF)2 (Ar = 2,4-t-Bu2C6H2 (11)，Ar = (12))，μ-CH2CH2[NCH( O)]2VCl(THF)} (14)和 [NCH( O)]2VCl(THF)} (15)，以进行比较聚合研究。二盐型化合物[2,6-i-Pr2-C6H3N+(H)CH( O)]2VCl2O (13)也被分离出来，推测是在一次偶然的水解反应中形成的。化合物2、5和13已被结构表征；化合物5中母体配体(L5)的分子结构也被报告。所有络合物均已检测乙烯和ε-己内酯聚合的能力，并将结果与已知相关的单核和双核对照进行比较，以评估可能的协同效应。化合物10和12被支持在改性SiO2上，通过XPS分析，并进行了均聚合（乙烯）和共聚合（1-己烯与乙烯）研究。
• Synthesis, Structural Characterization, and Ethylene Polymerization Behavior of the Vanadium(III) Complexes Bearing Salicylaldiminato Ligands
  作者：Ji-Qian Wu、Li Pan、Ning-Hai Hu、Yue-Sheng Li

  DOI：10.1021/om800097b

  日期：2008.8.1

  activities, and produced polymers with low molecular weight (Mw < 30 kg/mol) and broad molecular weight distributions at 70 °C. Complexes 3a−k were also effective catalyst precursors for ethylene polymerization. Even at 70 °C these complexes produced polyethylenes with unimodal distributions. These results indicated that the structural model of the salicylaldiminato vanadium(III) complexes greatly affected

  带有水杨基铝亚氨基配体（2a - k）的钒（III）络合物[RN═CH（ArO）] VCl 2（THF）2（Ar = C 6 H 4，R = Ph，2a ; p -CF 3 Ph，2b ; p -CH 3 Ph，2c ; 2,6-Me 2 Ph，2d ; 2,6- i Pr 2 Ph，2e ;环己基，2f ; Ar = C 6 H 3 t Bu（2），R = Ph，2g ; 2,6-我Pr 2Ph，2h ; Ar = C 6 H 2 t Bu 2（2,4），R = Ph，2i ; 2,6- i Pr 2 Ph，2j ; 在过量的三乙胺（TEA）存在下，用1.0当量的（RN═CH）ArOH在四氢呋喃（THF）中处理，由VCl 3（THF）3制备Ar = C 6 H 2 Br 2，R = Ph，2k） 。在过量TEA存在下，VCl 3（THF）3与2.0当量的（RN═CH）ArOH在THF中反