2-[4-[2-(4-Ethynyl-2,5-dihexylphenyl)ethynyl]-2,5-dihexylphenyl]ethynyl-tri(propan-2-yl)silane | 220280-82-0

• 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: 2-[4-[2-(4-Ethynyl-2,5-dihexylphenyl)ethynyl]-2,5-dihexylphenyl]ethynyl-tri(propan-2-yl)silane
• CAS: 220280-82-0
• 化学式: C₅₁H₇₈Si
• 分子量: 719.266
• InChiKey: AKFOCXNHNOVVOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.13
• 重原子数：
  52
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-[4-[2-(4-Ethynyl-2,5-dihexylphenyl)ethynyl]-2,5-dihexylphenyl]ethynyl-tri(propan-2-yl)silane 在 哌啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 2-(4-((4-((4-((4-ethynyl-2,5-dihexylphenyl)ethynyl)-2,5-dihexylphenyl)ethynyl)-2,5-dihexylphenyl)ethynyl)phenoxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  聚（对亚苯基亚乙炔基）的柔韧性如何？

  摘要：

  DOI：

  10.1002/anie.200602807
• 作为产物：
  描述：

  1,4-dihexyl-2,5-diiodobenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 哌啶 、 manganese(IV) oxide 、 氢氧化钾 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 2-[4-[2-(4-Ethynyl-2,5-dihexylphenyl)ethynyl]-2,5-dihexylphenyl]ethynyl-tri(propan-2-yl)silane
  参考文献：
  名称：

  末端乙炔单元使用不同极性的正交保护基合成单分散低聚（对亚苯基乙炔）

  摘要：

  从 1,4-二己基-2-(3-羟基丙基-1-炔基)-5-[2-(三异丙基甲硅烷基)乙炔基]苯开始，通过发散-收敛合成合成单分散低聚（对亚苯基乙炔基）（oligoPPE）并使用 Pd/Cu 催化的炔-芳基偶联。羟甲基 (HOM) 和三异丙基甲硅烷基 (TIPS) 用作乙炔部分的正交保护基团。极性 HOM 基团对产品的色谱行为有很强的影响，使纯化合物的分离变得非常容易。合成一直进行到九聚体。oligoPPE 被完全表征，包括吸收和发射光谱数据。

  DOI：

  10.1002/(sici)1099-0690(199901)1999:1<277::aid-ejoc277>3.0.co;2-r

文献信息

• Polar tagging in the synthesis of monodisperse oligo(<i>p</i>-phenyleneethynylene)s and an update on the synthesis of oligoPPEs
  作者：Dhananjaya Sahoo、Susanne Thiele、Miriam Schulte、Navid Ramezanian、Adelheid Godt

  DOI：10.3762/bjoc.6.57

  日期：——

  One important access to monodisperse (functionalized) oligoPPEs is based on the orthogonality of the alkyne protecting groups triisopropylsilyl and hydroxymethyl (HOM) and on the polar tagging with the hydroxymethyl moiety for an easy chromatographic separation of the products. This paper provides an update of this synthetic route. For the deprotection of HOM protected alkynes, γ-MnO₂ proved to be better than (highly) activated MnO₂. The use of HOM as an alkyne protecting group is accompanied by carbometalation as a side reaction in the alkynyl–aryl coupling. The extent of carbometalation can be distinctly reduced through substitution of HOM for 1-hydroxyethyl. The strategy of polar tagging is extended by embedding ether linkages within the solubilising side chains. With building blocks such as 1,4-diiodo-2,5-bis(6-methoxyhexyl) less steps are needed to assemble oligoPPEs with functional end groups and the isolation of pure compounds becomes simple. For the preparation of 1,4-dialkyl-2,5-diiodobenzene a better procedure is presented together with the finding that 1,4-dialkyl-2,3-diiodobenzene, a constitutional isomer of 1,4-dialkyl-2,5-diiodobenzene, is one of the byproducts.

  一种重要的单分散（官能化）寡PPEs的获取途径是基于炔基保护基三异丙基硅基和羟甲基（HOM）的正交性，以及使用羟甲基部分标记来实现产物的简便色谱分离。本文提供了这种合成途径的最新更新。对于HOM保护的炔烃的去保护，γ-MnO2被证明比（高度）活化的MnO2更好。使用HOM作为炔基保护基伴随着碳金属化作为炔基-芳基偶联的副反应。通过将HOM替换为1-羟基乙基，可以明显减少碳金属化的程度。极性标记策略通过在溶解侧链中嵌入醚键而得到扩展。使用建筑模块如1,4-二碘-2,5-双(6-甲氧基己基)可减少组装具有官能末端基团的寡PPEs所需的步骤，并使纯化化合物变得简单。对于1,4-二烷基-2,5-二碘苯的制备提出了更好的程序，同时发现1,4-二烷基-2,3-二碘苯，即1,4-二烷基-2,5-二碘苯的构成异构体，是其中的副产物。
• EPR Probes with Well-Defined, Long Distances between Two or Three Unpaired Electrons
  作者：Adelheid Godt、Corinna Franzen、Stephan Veit、Volker Enkelmann、Matthias Pannier、Gunnar Jeschke

  DOI：10.1021/jo005556j

  日期：2000.11.1

  The synthesis of rod- and star-shaped compounds carrying two or three spin labels as end groups is described. The unpaired electrons are 2.8-5.1 nm apart from each other. The shape-persistent scaffolds were obtained through Pd-Cu-catalyzed alkynyl-aryl coupling and Pd-Cu-catalyzed alkyne dimerization in the presence of oxygen using p-phenyleneethynylene as the basic shape-persistent building block. The spin label 1-oxyl-2,2,5,5-tetramethylpyrroline-3-carboxylic acid (4) was attached through esterification of the terminal phenolic OH groups of the scaffold.
• Hybrid Composites of Monodisperse π-Conjugated Rodlike Organic Compounds and Semiconductor Quantum Particles
  作者：Volker Hensel、Adelheid Godt、Ronit Popovitz-Biro、Hagai Cohen、Torben R. Jensen、Kristian Kjaer、Isabelle Weissbuch、Efrat Lifshitz、Meir Lahav

  DOI：10.1002/1521-3765(20020315)8:6<1413::aid-chem1413>3.0.co;2-6

  日期：2002.3.15

  Composite materials of quantum particles (Q-particles) arranged in layers within crystalline powders of pi-conjugated, rodlike dicarboxylic acids are reported. The synthesis of the composites, either as three-dimensional crystals or as thin films at the air-water interface, comprises a two-step process: 1) The preparation of the Cd salts 6(Cd), 8(Cd) or Pb salts 6(Pb), 8(Pb) of the oligo(p-phenyteneethynytene)dicarboxylic acids 6(H), 8(H), in which the metal ions are arranged in ribbons and are separated by the long axis of the organic molecules, as demonstrated by X-ray powder diffraction analysis of the solids and grazing incidence X-ray diffraction analysis of the films on water. 2) Topotactic solid/gas reaction of these salts with H2S to convert the metal ions into Q-particles of CdS or PbS embedded in the organic matrix that consists of the acids 6(H) and 8(H). These hybrid materials have been characterized by X-ray photoelectron spectroscopy and transmission electron microscopy.
• How Flexible Are Poly(para-phenyleneethynylene)s?
  作者：Adelheid Godt、Miriam Schulte、Herbert Zimmermann、Gunnar Jeschke

  DOI：10.1002/anie.200602807

  日期：2006.11.20
• Synthesis of Monodisperse Oligo(para-phenyleneethynylene)s Using Orthogonal Protecting Groups with Different Polarity for Terminal Acetylene Units
  作者：Hildegard Kukula、Stephan Veit、Adelheid Godt

  DOI：10.1002/(sici)1099-0690(199901)1999:1<277::aid-ejoc277>3.0.co;2-r

  日期：1999.1

  Monodisperse oligo(para-phenyleneethynylene)s (oligoPPEs) were synthesized by a divergent-convergent synthesis starting from 1,4-dihexyl-2-(3-hydroxyprop-1-ynyl)-5-[2-(triisopropylsilyl)ethynyl]benzene and using the Pd/Cu-catalyzed alkyne-aryl coupling. The groups hydroxymethyl (HOM) and triisopropylsilyl (TIPS) function as orthogonal protective groups for the acetylene moieties. The polar HOM group

  从 1,4-二己基-2-(3-羟基丙基-1-炔基)-5-[2-(三异丙基甲硅烷基)乙炔基]苯开始，通过发散-收敛合成合成单分散低聚（对亚苯基乙炔基）（oligoPPE）并使用 Pd/Cu 催化的炔-芳基偶联。羟甲基 (HOM) 和三异丙基甲硅烷基 (TIPS) 用作乙炔部分的正交保护基团。极性 HOM 基团对产品的色谱行为有很强的影响，使纯化合物的分离变得非常容易。合成一直进行到九聚体。oligoPPE 被完全表征，包括吸收和发射光谱数据。