1,2,4,5-tetrakis(4-methoxyphenyl)benzene | 1022331-29-8

• 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: 1,2,4,5-tetrakis(4-methoxyphenyl)benzene
• CAS: 1022331-29-8
• 化学式: C₃₄H₃₀O₄
• 分子量: 502.61
• InChiKey: IASGRMPAQOTMII-UHFFFAOYSA-N

物化性质

• 沸点：
  613.7±55.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,4,5-tetrakis(4-methoxyphenyl)benzene 在 iron(III) chloride 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 4.0h， 以93%的产率得到3,6,12,15-tetramethoxyphenanthro[9,10-b]-triphenylene
  参考文献：
  名称：

  Nonlinear Polyfused Aromatics with Extended π-Conjugation from Phenanthrotriphenylene, Tetracene, and Pentacene: Syntheses, Crystal Packings, and Properties

  摘要：

  New classes of nonlinear polyaromatics with extended conjugation at lateral and longitudinal directions from triphenylene, tetracene, and pentacene backbones are reported. These planar and twisted polyfused aromatics are obtained through specific and selective multifold Scholl reactions from predesigned polyaryls. These derivatives displayed shifted or perfect cofacial packing motifs. Single crystals of one derivative, phenanthro[9,10:b]triphenylene, were used as p-channel materials in fabricating transistor devices, which exhibited an average mobility of 0.38 cm(2) s(-1) and a maximum mobility reaching 1.15 cm(2) V-1 s(-1)

  DOI：

  10.1021/acs.joc.8b01582
• 作为产物：
  描述：

  1,2,4,5-四氯苯 、 4-甲氧基苯硼酸 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基二(1-金刚烷基)膦 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以99%的产率得到1,2,4,5-tetrakis(4-methoxyphenyl)benzene
  参考文献：
  名称：

  通过多氯苯的多个Suzuki-Miyaura反应有效合成多芳基苯的一般规程

  摘要：

  提出了通过多氯代苯的多个Suzuki-Miyaura反应高效合成多芳基化苯衍生物的通用方案。使用庞大且富含电子的膦配体，可以达到所需化合物的定量收率。此外，反应显示出良好的官能团耐受性，并允许使用空间需求的硼酸。

  DOI：

  10.1016/j.tet.2016.01.010

文献信息

• General and highly active catalyst for mono and double Hiyama coupling reactions of unreactive aryl chlorides in water
  作者：Dong-Hwan Lee、Ji-Young Jung、Myung-Jong Jin

  DOI：10.1039/c0cc03535a

  日期：——

  A new beta-diketiminatophosphane Pd catalyst was found to be highly effective in the mono and double Hiyama coupling reactions of unactivated aryl chlorides in water.

  发现一种新的β-二酮基亚氨基膦Pd催化剂在水中未活化的芳基氯化物的单和双Hiyama偶联反应中非常有效。
• Hydroxyphenylbenzene derivatives as glass forming molecules for high resolution photoresists
  作者：Anuja De Silva、Christopher K. Ober

  DOI：10.1039/b719108a

  日期：——

  This paper presents a fundamental study to relate molecular architecture to the amorphous properties of hydroxyphenylbenzene molecular glass derivatives. These studies demonstrates that the branched hydroxyphenylbenzene derivatives can form stable molecular glasses despite the π–π interactions present. Through this research, design concepts to stabilize the amorphous nature and to increase the glass transition temperature (Tg) based on asymmetric molecular structures, bulky substituents, conformation states and molecular size are explored. An understanding of such behavior is important for the development of hydroxyphenylbenzene derivatives as potential molecular photoresists for patterning below 50 nm. This research has helped to identify potential candidates to be evaluated as positive-tone photoresists for lithographic applications for extreme ultraviolet (EUV, λ = 13.4 nm) lithography. The first reported sub-30 nm feature sizes for hydroxyphenylbenzene derivatives were demonstrated with high Tg materials.

  本文通过基础研究，探讨了羟基苯基苯分子玻璃衍生物的分子结构与其非晶性质之间的关系。研究表明，尽管存在π-π相互作用，分枝羟基苯基苯衍生物仍能形成稳定的分子玻璃。通过这项研究，探索了基于不对称分子结构、庞大取代基、构象状态和分子尺寸来稳定非晶性质和提高玻璃化转变温度（Tg）的设计概念。对于开发潜在的分子光刻胶，用于50 nm以下图案化的羟基苯基苯衍生物，理解这种行为至关重要。这项研究有助于识别潜在候选物质，作为极紫外（EUV，波长=13.4 nm）光刻技术的正色调光刻胶。首次展示了Tg高的羟基苯基苯衍生物的亚30 nm特征尺寸。
• An Extremely Active and General Catalyst for Suzuki Coupling Reaction of Unreactive Aryl Chlorides
  作者：Dong-Hwan Lee、Myung-Jong Jin

  DOI：10.1021/ol102677r

  日期：2011.1.21

  2a acted as a powerful catalyst which allows easy access to the Suzuki coupling reaction of less reactive aryl chlorides under mild conditions. A wide range of sterically hindered and deactivated aryl chlorides could be efficiently coupled at a low catalyst loading of 0.1 mol %. Furthermore, this catalytic system also proved to be highly effective in one-pot multiple couplings.

  β-二酮亚氨基膦Pd络合物2a用作强力催化剂，可在温和条件下轻松进入反应性较低的芳基氯化物的Suzuki偶联反应。可以在0.1 mol％的低催化剂负载量下有效地偶联各种空间受阻和失活的芳基氯化物。此外，该催化体系在一锅多联中也被证明是非常有效的。
• Buchwald ligand-assisted Suzuki cross-coupling of polychlorobenzenes
  作者：Andrei A. Vasil’ev、Alexander S. Burukin、Galina M. Zhdankina、Sergei G. Zlotin

  DOI：10.1016/j.mencom.2021.04.039

  日期：2021.5

  Screening of four Buchwald ligands for the cross-coupling of isomeric di-, tri- and tetrachlorobenzenes with arylboronic acids revealed that good yields of exhaustive substitution can be best provided by 2-dicyclohexylphosphino-2′-(dimethylamino) biphenyl (DavePHOS).

  筛选用于异构二、三和四氯苯与芳基硼酸交叉偶联的四种 Buchwald 配体表明，2-二环己基膦基-2'-（二甲氨基）联苯 (DavePHOS) 可以最好地提供良好的穷举取代收率。
• Nickel Bromide Catalyzed Ligand‐Free and Activator‐less Suzuki Coupling Reactions
  作者：Khadimul Islam、Vinay Arora、Vikas、Bedabara Nag、Akshai Kumar

  DOI：10.1002/cctc.202200440

  日期：2022.8.19

  Readily available and inexpensive NiBr2 has been used for the first time to accomplish the ligand-free and activator-less catalytic Suzuki coupling of a variety of aryl halides (ca. 60 examples) with several arylboronic acids in high yields under ambient conditions with good functional group tolerance.

  易于获得且价格低廉的NiBr 2首次用于在环境条件下以高产率实现各种芳基卤化物（约 60 个实例）与几种芳基硼酸的无配体和无活化剂催化 Suzuki 偶联，并具有良好的官能团耐受性。