N-(3,5-di-tert-butylsalicylidene)-3,5-bis(trifluoromethyl)aniline | 353493-58-0

• 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-(3,5-di-tert-butylsalicylidene)-3,5-bis(trifluoromethyl)aniline
• 英文别名: 2-(((3,5-bis(trifluoromethyl)phenyl)imino)methyl)-4,6-di-tert-butylphenol；3,5-bis(trifluoromethyl)aniline-3,5-di-tert-butylsalicylaldimine；2-[[3,5-Bis(trifluoromethyl)phenyl]iminomethyl]-4,6-ditert-butylphenol
• CAS: 353493-58-0
• 化学式: C₂₃H₂₅F₆NO
• 分子量: 445.448
• InChiKey: FUWXZSUBWGWSBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  31
• 可旋转键数：
  4
• 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：
  8

反应信息

• 作为反应物：
  描述：

  N-(3,5-di-tert-butylsalicylidene)-3,5-bis(trifluoromethyl)aniline 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Cameron, Paul A.; Gibson, Vernon C.; Redshaw, Carl, Journal of the Chemical Society. Dalton Transactions (2001), 2001, # 9, p. 1472 - 1476

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二叔丁基水杨醛 、 间二(三氟甲基)苯胺 在 甲酸 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以74%的产率得到N-(3,5-di-tert-butylsalicylidene)-3,5-bis(trifluoromethyl)aniline
  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

• Syndiospecific Living Catalysts for Propylene Polymerization: Effect of Fluorination on Activity, Stereoselectivity, and Termination
  作者：Andrew F. Mason、Jun Tian、Philip D. Hustad、Emil B. Lobkovsky、Geoffrey W. Coates

  DOI：10.1560/xkld-hwth-q45e-1v9g

  日期：2002.12

  The polymerization of propylene using a variety of fluorinated bis(phenoxyimine)titanium complexes is reported. The synthesis of ten complexes containing varying fluorinated N‐aryl substituents is described. X‐ray structural and solution NMR data indicate that these complexes are C₂‐symmetric in the solid state, although in some cases C₁‐symmetric isomers are observed in solution. When activated with methylalumoxane, all complexes formed syndiotactic polypropylene. Catalysts with ortho‐fluorine substituents formed polymers with very narrow molecular weight distributions, indicative of a living polymerization. Catalysts with fluorine in at least the ortho and para positions exhibited the highest syndio‐specificities. Catalysts with meta‐ or para‐fluorine‐containing substituents were more active for propylene polymerization than the corresponding non‐fluorinated catalyst.

  摘要 报道了使用各种氟化双（苯氧亚胺）钛络合物聚合丙烯的情况。文中介绍了含有不同氟化 N-芳基取代基的十种络合物的合成过程。X 射线结构和溶液核磁共振数据表明，这些络合物在固态下是 C2 对称的，但在某些情况下，在溶液中也能观察到 C1 对称的异构体。当用甲基铝氧烷活化时，所有配合物都会形成对位聚丙烯。带有正氟取代基的催化剂形成的聚合物分子量分布非常窄，表明是活聚合。至少在正位和对位含有氟的催化剂具有最高的联合特异性。与相应的非含氟催化剂相比，含偏氟或对位氟取代基的催化剂对丙烯聚合的活性更高。
• The orthopalladation dinuclear [Pd(L1)(μ-OAc)]2, [Pd(L2)(μ-OAc)]2 and mononuclear [Pd(L3)2] complexes with [N, C, O] or [N, O] containing ligands: Synthesis, spectral characterization, electrochemistry and catalytic properties
  作者：Ahmet Kilic、Dilek Kilinc、Esref Tas、Ismail Yilmaz、Mustafa Durgun、Ismail Ozdemir、Sedat Yasar

  DOI：10.1016/j.jorganchem.2009.12.003

  日期：2010.3

  hydrogenation of both nitrobenzene and cyclohexene. These metal complexes were also tested as catalysts in Suzuki–Miyaura coupling of aryl bromide in the presence of K2CO3. The catalytic studies showed that the introduction of different groups on the salicyl ring of the molecules effected the catalytic activity towards hydrogenation of nitrobenzene and cyclohexene in DMF at 25 and 45 °C. The Pd(II) complexes

  在无水乙醇中用乙酸钯（II）处理水杨醛亚胺配体（L 1 H，L 2 H，L 3 H，L 4 H和L 5 H），得到原钯双核[Pd（L 1）（μ-OAc） ] 2，[Pd（L 2）（μ-OAc）] 2和具有四齿配体[N，C，O]或[N，O]部分的单核[Pd（L 3）2 ]。配体L 1 H和L 2 H通过亚胺氮和芳族邻碳原子配位，而配体L 3H通过亚胺氮和酚氧原子配位。Pd（II）配合物具有正方形平面结构，被发现是硝基苯和环己烯加氢的有效催化剂。在K 2 CO 3存在下，这些金属配合物还作为芳基溴的Suzuki – Miyaura偶联反应的催化剂进行了测试。。催化研究表明，在分子的水杨基环上引入不同的基团会影响DMF在25和45°C下对硝基苯和环己烯加氢的催化活性。由廉价材料轻松制备的Pd（II）配合物可用作各种不同C-C偶联反应（铃木-宫浦反应）的多功能高效催化剂。通过UV-Vis，FT-IR，1
• Hydroalkylation of Aryl Alkenes with Organohalides Catalyzed by Molybdenum Oxido Based Lewis Pairs
  作者：Niklas Zwettler、Antoine Dupé、Sumea Klokić、Angela Milinković、Dado Rodić、Simon Walg、Dmytro Neshchadin、Ferdinand Belaj、Nadia C. Mösch‐Zanetti

  DOI：10.1002/adsc.202000425

  日期：2020.8.4

  Three molybdenum(VI) dioxido complexes [MoO2(L)2] bearing Schiff base ligands were reacted with B(C6F5)3 to afford the corresponding adducts [MoOOB(C6F5)3}(L)2], which were fully characterized. They exhibit Frustrated Lewis‐Pairs reactivity when reacting with silanes. Especially, the [MoOOB(C6F5)3}(L)2] complex with L=2,4‐dimethyl‐6‐((phenylimino)methyl)phenol proved to be active as catalyst for

  三个带有席夫碱配体的二氧化钼(VI)络合物[MoO 2 (L) 2 ]与B(C 6 F 5 ) 3反应，得到相应的加合物[MoOOB(C 6 F 5 ) 3 }(L) 2 ]，其特征得到充分表征。当与硅烷反应时，它们表现出受阻路易斯对反应性。特别是，[MoOOB(C 6 F 5 ) 3 }(L) 2 ]与L=2,4-二甲基-6-((苯基亚氨基)甲基)苯酚的络合物被证明具有作为芳基加氢烷基化催化剂的活性。烯烃与有机卤化物以及有机卤化物与脂肪族烯烃的原子转移自由基加成 (ATRA)。使用低催化剂负载量，由简单的烯烃和有机卤化物（如氯仿或溴仿）合成了一系列具有进一步衍生化潜力的偕二氯化物和偕二溴化物化合物。
• Molybdenum(VI) Bis(imido) Complexes: From Frustrated Lewis Pairs to Weakly Coordinating Cations
  作者：Angela Milinkovic、Antoine Dupé、Ferdinand Belaj、Nadia C. Mösch‐Zanetti

  DOI：10.1002/chem.202201867

  日期：2022.10.4

  Demonstration of how to teach well-known molybdenum bis(imido) complexes new and unexpected reactivities. These frustrated Lewis pairs (FLP) perform heterolytic dihydrogen splitting under ion pair formation consisting of molybdenum amido cations and hydroborates. They prove to be effective catalysts in the hydrosilylation of aldehydes. The molybdenum cations influence the outcome pointing towards their

  演示如何教授著名的钼双（亚氨基）配合物新的和意想不到的反应性。这些受挫路易斯对（FLP）在由钼酰胺阳离子和硼酸根组成的离子对形成下进行异解二氢分裂。它们被证明是醛氢化硅烷化的有效催化剂。钼阳离子会影响结果，表明它们作为弱配位阳离子 (WCC) 的行为。
• Synthesis, characterization, crystal structure, redox-reactivity and antiproliferative activity studies of Cu(II) and Pd(II) complexes with F, CF3 bearing 3,5-di-tert-butylsalicylaldimines
  作者：Veli T. Kasumov、Onur Sahin、Hatice Gümüşhan Aktas

  DOI：10.1016/j.poly.2016.03.061

  日期：2016.9

  In this work, based on 3,5-di-tert-butyl-2-hydroxybenzaldehyde and F, CF3-substituted anilines [2-fluoro-3-(trifluromethyl)aniline, 2-fluoro-5-(trifluromethyl)aniline, 3,5-bis(trifluoromethylaniline and 2-fluoro-3-(trifluromethyl)benzylaniline], the corresponding salicylaldimine ligands (HLx, X = 1, 2, 3, 4) and their CuL2x and PdL2x complexes were synthesized. The structures of these compounds were characterized by spectroscopic (IR, UV/Vis, H-1 and F-19 NMR, ESR) and X-ray diffraction techniques. Chemical oxidation of the tert-buylated HLx ligands and their CuLx2 complexes using Ce(IV) under anaerobic and aerobic conditions at room temperature (r.t.) in DMF solution revealed the generation of phenoxyl radicals. An X-ray structural study revealed that thanks to CH....F and CH.....pi bonds both the CuL21 and PdL21 molecules crystallize as hydrated dimers that pack differently. The antiproliferative potentials of all the compounds against Mat-LyLu cell lines were determined. (C) 2016 Elsevier Ltd. All rights reserved.