2,2',2'',2'''-(1,2-ethenediylidene)tetrakis(4-tert-butylphenol) | 464170-59-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,2',2'',2'''-(1,2-ethenediylidene)tetrakis(4-tert-butylphenol)
• 英文别名: tetrakis(2-hydroxy-5-tert-butylphenyl)ethene；tetrakis(5-tert-butyl-2-hydroxyphenyl)ethene；4-Tert-butyl-2-[1,2,2-tris(5-tert-butyl-2-hydroxyphenyl)ethenyl]phenol；4-tert-butyl-2-[1,2,2-tris(5-tert-butyl-2-hydroxyphenyl)ethenyl]phenol
• CAS: 464170-59-0
• 化学式: C₄₂H₅₂O₄
• 分子量: 620.872
• InChiKey: OLVYEAFUPFDGCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  46
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2',2'',2'''-(1,2-ethenediylidene)tetrakis(4-tert-butylphenol) 在 四氯化碳 、 溴 作用下， 以 溶剂黄146 为溶剂， 反应 16.0h， 以92%的产率得到tetrakis(3-bromo-5-tert-butyl-2-hydroxyphenyl)ethene
  参考文献：
  名称：

  Ortho-Silylated Derivatives of Tetrakis(2-hydroxyphenyl)ethene: A Sterically Isolated Structural Model for Oxo-Surface Binding Domains

  摘要：

  The introduction of sterically isolating ortho-trialkylsilyl, -aryldialkylsilyl, and -diarylalkylsilyl substituents onto the structurally preorganized tetrakis(2-hydroxyphenyl)ethene ligand framework has been accomplished by a 4-fold retro-Brook rearrangement. Installation of the most sterically demanding silyl substituents required the development of an iterative procedure, involving successive double silylation/metalation/migration sequences without the isolation of intermediates. This system was designed to function as a soluble structural model for the planar binding domains of heterogeneous "oxo-surfaces" of silica and alumina supports.

  DOI：

  10.1021/ol801427w
• 作为产物：
  描述：

  4-叔丁基茴香醚 在 nickel(IV) oxide 、 正丁基锂 、 四甲基乙二胺 、 三溴化硼 、 一水合肼 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 、 正丁醇 为溶剂， 反应 18.0h， 生成 2,2',2'',2'''-(1,2-ethenediylidene)tetrakis(4-tert-butylphenol)
  参考文献：
  名称：

  四（2-羟基苯基）乙烯和衍生物。用于多金属配位化学和催化的结构预组织四齿配体系统

  摘要：

  已开发出一种用于多金属配位化学的拓扑独特、构象受限的四齿配体系统：四（2-羟基苯基）乙烯 (1a) 和取代衍生物。该设计利用四苯基乙烯核的平面性为大致方形的氧结合阵列赋予刚性，同时保持与围绕芳基-乙烯碳-碳键旋转相关的一定程度的构象迁移率。四（2-羟基苯基）乙烯衍生物旨在通过螯合配位模式促进多种金属桥接。配体由苯甲醚或 4-叔丁基苯甲醚通过 2,2'-二甲氧基二苯甲酮腙 4a,b 分四步合成。通过使用过氧化镍氧化腙原位制备的相应二芳基重氮甲烷的酸催化分解，以高产率制备空间位阻邻位取代的四苯基乙烯核。使用三溴化硼对甲基醚进行脱保护得到四（2-羟基苯基）乙烯（1a），通过 X 射线晶体学表征，和四（5-叔丁基-2-羟基苯基）乙烯（1b）。3-位上的空间隔离取代基可以通过克莱森重排/氢化安装，有效地提供四（3-n-丙基-2-羟基苯基）乙烯（6）。为了说明这种前所未有的配体类别的潜在应用，报道了两

  DOI：

  10.1021/ja027436u

文献信息

• Coordination chemistry of the tetrakis(2-hydroxyphenyl)ethene support mimic — Polymetallic magnesium, aluminum, and titanium derivatives
  作者：Udo H Verkerk、Robert McDonald、Jeffrey M Stryker

  DOI：10.1139/v05-108

  日期：2005.6.1

  The crystal structures of magnesium, aluminum, and titanium coordination complexes of the structurally preorganized tetrakis(2-hydroxyphenyl)ethene are reported. As a result of the absence of steric shielding and the conformational flexibility of the ligand, pseudo-dimeric complexes are formed instead of crown- or raft-like compounds. The unsubstituted tetrakis(2-hydroxyphenyl)ethene ligand thus emulates the complexation characteristics of the sterically open calix[4]arene system.Key words: coordination chemistry, polymetallic, titanium complexes, magnesium complexes, aluminum complexes, tetrakis(2-hydroxyphenyl)ethene ligands, crystal structures.

  报道了镁、铝和钛配位化合物的晶体结构，这些化合物使用结构预组合的四羟基苯乙烯四酚配体。由于缺乏立体屏蔽和配体的构象灵活性，形成了伪二聚体配合物，而不是冠状或筏状化合物。因此，未取代的四羟基苯乙烯四酚配体模拟了具有立体开放性的杯[4]芳烃系统的络合特性。关键词：配位化学，多金属，钛配合物，镁配合物，铝配合物，四羟基苯乙烯配体，晶体结构。
• Strong π-interactions between tantalum and apical ligands in square pyramidal complexes supported by a rigid tetradentate spectator ligand
  作者：Richard S. Morris、Gino G. Lavoie

  DOI：10.1016/j.ica.2015.06.005

  日期：2015.8

  The synthesis of new tantalum(V) square pyramidal complexes supported by the tert-butyl-substituted (ethenediylidene) tetraphenoxide spectator ligand (TPO) and their reactivity are herein described. The tantalum ethoxide (TPO)Ta(OCH2CH3) (1) and dimethylamide (TPO)Ta(NMe2) (2) complexes were prepared and structurally characterised, giving valuable insight into pi-interactions between the metal centre and the apical ligand. The solid-state structures confirmed the geometry of both complexes, with TPO forming the base of the square pyramidal structure and the ethoxide and dimethylamide ligands occupying the apical position. Bond lengths and angles from the structures indicate significant double bond character between the metal and the apical ligand with very short metal-oxygen and metal-nitrogen bonds in 1 and 2, respectively, which results from donation of pi-electron density from the heteroatom into empty metal d pi-orbitals. Reaction of (TPO)Ta(OCH2CH3) (1) and (TPO)Ta(NMe2) (2) with trimethylaluminum gave the methyl complex (TPO)Ta(CH3) (3). Complexes 1 and 2 were cleanly regenerated by addition of ethanol and dimethylamine to complex 3. Addition of strong Bronsted acids to these complexes gave mixtures of compounds that could not be characterised, possibly due to competing protonation of the spectator TPO ligand or formation of oligomeric species. (C) 2015 Elsevier B.V. All rights reserved.
• Tetrakis(2-hydroxyphenyl)ethene and Derivatives. A Structurally Preorganized Tetradentate Ligand System for Polymetallic Coordination Chemistry and Catalysis
  作者：Udo Verkerk、Megumi Fujita、Trevor L. Dzwiniel、Robert McDonald、Jeffrey M. Stryker

  DOI：10.1021/ja027436u

  日期：2002.8.1

  chemistry has been developed: tetrakis(2-hydroxyphenyl)ethene (1a) and substituted derivatives. The design exploits the planarity of the tetraphenylethylene core to impart rigidity to the roughly square oxygen binding array, while maintaining a degree of conformational mobility associated with rotation about the aryl-ethylene carbon-carbon bonds. Tetrakis(2-hydroxyphenyl)ethene derivatives are designed to promote

  已开发出一种用于多金属配位化学的拓扑独特、构象受限的四齿配体系统：四（2-羟基苯基）乙烯 (1a) 和取代衍生物。该设计利用四苯基乙烯核的平面性为大致方形的氧结合阵列赋予刚性，同时保持与围绕芳基-乙烯碳-碳键旋转相关的一定程度的构象迁移率。四（2-羟基苯基）乙烯衍生物旨在通过螯合配位模式促进多种金属桥接。配体由苯甲醚或 4-叔丁基苯甲醚通过 2,2'-二甲氧基二苯甲酮腙 4a,b 分四步合成。通过使用过氧化镍氧化腙原位制备的相应二芳基重氮甲烷的酸催化分解，以高产率制备空间位阻邻位取代的四苯基乙烯核。使用三溴化硼对甲基醚进行脱保护得到四（2-羟基苯基）乙烯（1a），通过 X 射线晶体学表征，和四（5-叔丁基-2-羟基苯基）乙烯（1b）。3-位上的空间隔离取代基可以通过克莱森重排/氢化安装，有效地提供四（3-n-丙基-2-羟基苯基）乙烯（6）。为了说明这种前所未有的配体类别的潜在应用，报道了两
• <i>Ortho</i>-Silylated Derivatives of Tetrakis(2-hydroxyphenyl)ethene: A Sterically Isolated Structural Model for Oxo-Surface Binding Domains
  作者：Mee-Kyung Chung、Owen C. Lightbody、Jeffrey M. Stryker

  DOI：10.1021/ol801427w

  日期：2008.9.1

  The introduction of sterically isolating ortho-trialkylsilyl, -aryldialkylsilyl, and -diarylalkylsilyl substituents onto the structurally preorganized tetrakis(2-hydroxyphenyl)ethene ligand framework has been accomplished by a 4-fold retro-Brook rearrangement. Installation of the most sterically demanding silyl substituents required the development of an iterative procedure, involving successive double silylation/metalation/migration sequences without the isolation of intermediates. This system was designed to function as a soluble structural model for the planar binding domains of heterogeneous "oxo-surfaces" of silica and alumina supports.