2,4-di-tert-butyl-6-{[2'-(pyridin-2-yl)benzylamino]methyl}-phenol | 676365-39-2

• 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'-(pyridin-2-yl)benzylamino]methyl}-phenol
• 英文别名: 2-((N-benzylpyrid-2-ylmethylamino)methyl)-4,6-di-tert-butylphenol；2,4-di-tert-butyl-6-[2'-((pyridin-2-yl)benzylamino)methyl]phenol；2-((N-benzylpyrid-2-ylmethylamino)methyl)-4,6-di-tertbutylphenol；2-[[Benzyl(pyridin-2-ylmethyl)amino]methyl]-4,6-ditert-butylphenol；2-[[benzyl(pyridin-2-ylmethyl)amino]methyl]-4,6-ditert-butylphenol
• CAS: 676365-39-2
• 化学式: C₂₈H₃₆N₂O
• 分子量: 416.607
• InChiKey: HHNAJYHIUSCBJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis(bis(trimethylsilyl)amido)zinc(II) 、 2,4-di-tert-butyl-6-{[2'-(pyridin-2-yl)benzylamino]methyl}-phenol 以 甲苯 为溶剂， 以76%的产率得到
  参考文献：
  名称：

  Zinc and enolato-magnesium complexes based on bi-, tri- and tetradentate aminophenolate ligands

  摘要：

  一系列潜在的四齿、三齿和二齿氨基酚前配体([L1]H–[L5]H)与镁和锌衍生物的配位化学已被研究。前配体[L1]H、[L2]H和[L3]H与等量的ZnEt2或Zn(N(SiMe3)2)2在室温下在甲苯中反应，通过乙烷或胺消除，干净地得到乙基和酰胺基锌配合物1–4。从三齿前配体[L4]H衍生的配合物[L4]ZnEt(5)和[L4]Zn(N(SiMe3)2)2(6)分别通过类似的烷烃和胺消除协议，以84%和76%的产率制备。二齿前配体[L5]H与ZnEt2或Zn(N(SiMe3)2)2在甲苯中的1:1反应，采用不同的反应协议，系统地生成了双(配体)配合物[L5]2Zn(7)和相应的乙基-{[L5]ZnEt}n(8; n = 1或2)或酰胺- {[L5]Zn(N(SiMe3)2)}n配合物(9; n = 1或2)的混合物。镁醇盐配合物10和11的合成采用了一锅法两步程序，首先将前配体[L1]H和[L4]H与等量的Mg(n,sBu)2反应生成相应的{[Ln]Mg(n,sBu)}n物种，然后进一步与等量的2,4,6-Me3C6H2COMe反应。所有配合物均通过多核NMR、元素分析以及五配位镁配合物10和四配位锌配合物3–6的单晶X射线衍射研究进行了表征。初步研究表明，镁物种10和11以及锌配合物1和5即使与等量的Li[OC(CH2)(2,4,6-Me3C6H2)]结合，也不是甲基丙烯酸甲酯聚合的有效引发剂，而锌配合物2, 4和6在20°C下对于ε-己内酯和rac-乳酸的环开聚合是有效的引发剂。

  DOI：

  10.1039/b812754a
• 作为产物：
  描述：

  1-phenyl-N-(pyridin-2-ylmethylene)methanamine 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 72.0h， 生成 2,4-di-tert-butyl-6-{[2'-(pyridin-2-yl)benzylamino]methyl}-phenol
  参考文献：
  名称：

  邻苯二酚双加氧酶的酶-底物加合物的功能模型：面部配位三齿酚盐配体的Lewis碱性调节双加氧速率和产物选择性

  摘要：

  摘要一些[Fe（L）（DBC）（CH3OH）]类型的3,5-二叔丁基邻苯二酚铁盐（DBC2-）加合物，其中L是三齿取代的单酚盐配体，例如2-（ （N-苄基吡啶-2-基甲基氨基）甲基）苯酚（H（L1）），2-（（N-苄基吡啶-2-基甲基氨基）-甲基）-4,6-二甲基苯酚（H（L2）），2-（ （N-苄基吡啶-2-基甲基氨基）甲基）-4,6-二叔丁基苯酚（H（L3））和2-（（N-苄基吡啶-2-基甲基氨基）甲基）-4-硝基苯酚（H（L4） ）），已通过元素分析和ESI-MS分析进行了表征。在甲醇溶液中已经研究了加合物的光谱和电化学性质以及双加氧酶活性。当酚盐环上的取代基从释放电子变为吸收电子时，DBSQ / DBC2-偶对的氧化还原电势移到一个更正的值，表明铁（III）-儿茶酚酸键的价格增加。所有的复合物都使用分子氧引发DBC2-的裂解，以提供内（I）和外二醇（E）裂解产物，产物选择性（E /

  DOI：

  10.1016/j.ica.2011.08.025

文献信息

• Half-sandwich η6-benzene Ru(II) complexes of phenolate-based pyridylalkylamine/alkylamine ligands: Synthesis, structure, and stabilization of one-electron oxidized species
  作者：Haritosh Mishra、Rabindranath Mukherjee

  DOI：10.1016/j.jorganchem.2007.03.041

  日期：2007.7

  Four half-sandwich ruthenium(II) complexes [(eta(6)-C6H6)Ru(L-1-O)][PF6] (1), [(eta(6)-C6H6)Ru(L-2-O)][PF6] (2), [(eta(6)-C6H6)Ru(L-3-O)][PF6] (3), [(eta(6)-C6H6)Ru(L-4-O)][PF6] (4a), and [(eta(6)-C6H6)Ru(L-4-O)][BPh4] (4b) [L-1-OH, 4-nitro-6-[(2'-(pyridin-2-yl)ethyl)methylamino]methyl}-phenol; L-2-OH, 2,4-di-tert-butyl-6-[(2'-(pyridin-2-yl)ethyl)methylamino]methyl}-phenol; L-3-OH, 2,4-di-tert-butyl-6-[2'-((pyridin-2-yl)benzylamino)methyl}-phenol; L-4-OH, 2,4-di-tert-butyl-6-[(2'-imethylaminoethyl)methylamino]methyl}-phenol (L-4-OH)], supported by a systematically varied series of tridentate phenolate-based pyridylalkylamine and alkylamine ligands are reported. The molecular structures of 1-3, 4a, and 4b have been elucidated in solution using H-1 NMR spectroscopy and of 1, 3, and 4b in the solid state by X-ray crystallography. Notably, due to coordination by the ligands the Ru center assumes a chiral center and in turn the central amine nitrogen also becomes chiral. The H-1 NMR spectra exhibit only one set of signals, suggesting that the reaction is completely diastereoselective [1: S-Ru,S-N/R-Ru,R-N; 2: R-Ru,R-N/S-Ru,S-N; 3: S-Ru,R-N/R-Ru,S-N; 4b: S-Ru,R-N/R-Ru,S-N]. The crystal packing in 1 and 3 is stabilized by C-H(center dot center dot center dot)0 interactions, in 4b no meaningful secondary interactions are observed. From the standpoint of generating phenoxyl radical, as investigated by cyclic voltammetry (CV), complex 1 is redox-inactive in MeCN solution. However, 2, 3, and 4a generate a one-electron oxidized phenoxyl radical coordinated species [2](2+center dot), [3](2+center dot), and [4a](2+center dot), respectively. The radical species are characterized by CV, UV-Vis, and EPR spectroscopy. The stability of the radical species has been determined by measuring the decay constant (UV-Vis spectroscopy). (C) 2007 Elsevier B.V. All rights reserved.
• How Single and Bifurcated Hydrogen Bonds Influence Proton-Migration Rate Constants, Redox, and Electronic Properties of Phenoxyl Radicals
  作者：Fabrice Thomas、Olivier Jarjayes、Hélène Jamet、Sylvain Hamman、Eric Saint-Aman、Carole Duboc、Jean-Louis Pierre

  DOI：10.1002/anie.200352368

  日期：2004.1.23
• Zinc and enolato-magnesium complexes based on bi-, tri- and tetradentate aminophenolate ligands
  作者：Zhanjiang Zheng、Gang Zhao、Rémy Fablet、Miloud Bouyahyi、Christophe M. Thomas、Thierry Roisnel、Osvaldo Casagrande Jr、Jean-François Carpentier

  DOI：10.1039/b812754a

  日期：——

  The coordination chemistry of a series of potentially tetra-, tri- and bi-dentate aminophenol pro-ligands ([L1]H–[L5]H) with magnesium and zinc derivatives has been studied. Reactions of the pro-ligands [L1]H, [L2]H and [L3]H with one equiv. of ZnEt2 or Zn(N(SiMe3)2)2 in toluene at room temperature afford cleanly, viaethane or amine elimination, the ethyl- and amido-zinc complexes 1–4. Complexes [L4]ZnEt (5) and [L4]Zn(N(SiMe3)2)2 (6) derived from the tridentate pro-ligand [L4]H were prepared in 84% and 76% yields, following similar alkane and amine elimination protocols, respectively. The 1 : 1 reactions of bidentate pro-ligand [L5]H with ZnEt2 or Zn(N(SiMe3)2)2 in toluene using different reaction protocols systematically yielded mixtures of the bis(ligand) complex [L5]2Zn (7) and the corresponding ethyl-[L5]ZnEt}n (8; n = 1 or 2) or amido- [L5]Zn(N(SiMe3)2)}n complexes (9; n = 1 or 2). The synthesis of magnesium-enolate complexes 10 and 11 was carried out in a one-pot, two-step procedure by first reacting pro-ligands [L1]H and [L4]H with one equiv. of Mg(n,sBu)2 to generate the corresponding [Ln]Mg(n,sBu)}n species, which were further reacted with one equiv. of 2,4,6-Me3C6H2COMe. All complexes have been characterized by multinuclear NMR, elemental analysis, and by single-crystal X-ray diffraction studies for five-coordinate magnesium complex 10, and four-coordinate Zn complexes 3–7. Preliminary studies indicate that magnesium species 10 and 11 as well as zinc complexes 1 and 5 are not active initiators for the polymerization of methyl methacrylate, even in combination with one equiv. of Li[OC(CH2)(2,4,6-Me3C6H2)], while zinc complexes 2, 4 and 6 are effective initiators for the ring-opening polymerization of ε-caprolactone and rac-lactide at 20 °C.

  一系列潜在的四齿、三齿和二齿氨基酚前配体([L1]H–[L5]H)与镁和锌衍生物的配位化学已被研究。前配体[L1]H、[L2]H和[L3]H与等量的ZnEt2或Zn(N(SiMe3)2)2在室温下在甲苯中反应，通过乙烷或胺消除，干净地得到乙基和酰胺基锌配合物1–4。从三齿前配体[L4]H衍生的配合物[L4]ZnEt(5)和[L4]Zn(N(SiMe3)2)2(6)分别通过类似的烷烃和胺消除协议，以84%和76%的产率制备。二齿前配体[L5]H与ZnEt2或Zn(N(SiMe3)2)2在甲苯中的1:1反应，采用不同的反应协议，系统地生成了双(配体)配合物[L5]2Zn(7)和相应的乙基-[L5]ZnEt}n(8; n = 1或2)或酰胺- [L5]Zn(N(SiMe3)2)}n配合物(9; n = 1或2)的混合物。镁醇盐配合物10和11的合成采用了一锅法两步程序，首先将前配体[L1]H和[L4]H与等量的Mg(n,sBu)2反应生成相应的[Ln]Mg(n,sBu)}n物种，然后进一步与等量的2,4,6-Me3C6H2COMe反应。所有配合物均通过多核NMR、元素分析以及五配位镁配合物10和四配位锌配合物3–6的单晶X射线衍射研究进行了表征。初步研究表明，镁物种10和11以及锌配合物1和5即使与等量的Li[OC(CH2)(2,4,6-Me3C6H2)]结合，也不是甲基丙烯酸甲酯聚合的有效引发剂，而锌配合物2, 4和6在20°C下对于ε-己内酯和rac-乳酸的环开聚合是有效的引发剂。
• Functional models for enzyme–substrate adducts of catechol dioxygenase enzymes: The Lewis basicity of facially coordinating tridentate phenolate ligands tunes the rate of dioxygenation and product selectivity
  作者：Kusalendiran Visvaganesan、Somasundaram Ramachitra、Mallayan Palaniandavar

  DOI：10.1016/j.ica.2011.08.025

  日期：2011.11

  Abstract A few iron(III) 3,5-di-tert-butylcatecholate (DBC2−) adducts of the type [Fe(L)(DBC)(CH3OH)], where L is a tridentate substituted monophenolate ligand such as 2-((N-benzylpyrid-2-ylmethylamino)methyl)phenol (H(L1)), 2-((N-benzylpyrid-2-ylmethylamino)-methyl)-4,6-dimethylphenol (H(L2)), 2-((N-benzylpyrid-2-ylmethylamino)methyl)-4,6-di-tert-butylphenol (H(L3)) and 2-((N-benzylpyrid-2-ylmeth

  摘要一些[Fe（L）（DBC）（CH3OH）]类型的3,5-二叔丁基邻苯二酚铁盐（DBC2-）加合物，其中L是三齿取代的单酚盐配体，例如2-（ （N-苄基吡啶-2-基甲基氨基）甲基）苯酚（H（L1）），2-（（N-苄基吡啶-2-基甲基氨基）-甲基）-4,6-二甲基苯酚（H（L2）），2-（ （N-苄基吡啶-2-基甲基氨基）甲基）-4,6-二叔丁基苯酚（H（L3））和2-（（N-苄基吡啶-2-基甲基氨基）甲基）-4-硝基苯酚（H（L4） ）），已通过元素分析和ESI-MS分析进行了表征。在甲醇溶液中已经研究了加合物的光谱和电化学性质以及双加氧酶活性。当酚盐环上的取代基从释放电子变为吸收电子时，DBSQ / DBC2-偶对的氧化还原电势移到一个更正的值，表明铁（III）-儿茶酚酸键的价格增加。所有的复合物都使用分子氧引发DBC2-的裂解，以提供内（I）和外二醇（E）裂解产物，产物选择性（E /