((4-(tert-butyl)phenyl)ethynyl)triisopropylsilane | 945773-25-1

• 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: ((4-(tert-butyl)phenyl)ethynyl)triisopropylsilane
• 英文别名: 2-(4-Tert-butylphenyl)ethynyl-tri(propan-2-yl)silane
• CAS: 945773-25-1
• 化学式: C₂₁H₃₄Si
• 分子量: 314.586
• InChiKey: XRKKKXMUVSDGRN-UHFFFAOYSA-N

物化性质

• 沸点：
  356.0±25.0 °C(Predicted)
• 密度：
  0.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.55
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  ((4-(tert-butyl)phenyl)ethynyl)triisopropylsilane 在 四(三苯基膦)钯 哌啶 、 potassium fluoride 、 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 1-叔丁基-4-[2-(4-叔丁基苯基)乙炔基]苯
  参考文献：
  名称：

  Molecular machines: synthesis and characterization of two prototypes of molecular wheelbarrows

  摘要：

  Technomimetic molecules are molecules designed to imitate macroscopic objects at the molecular level, also transposing the motions that these objects are able to undergo. This article focuses on the synthesis of two polyaromatic hydrocarbons designed by analogy with macroscopic wheelbarrows. The molecular wheelbarrows are synthesized following a modular strategy based on sequential double Knoevenagel and Diels-Alder reactions. Our strategy allowed to easily vary the chemical nature of the handles, which is crucial for subsequent manipulation with an STM tip. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.019
• 作为产物：
  描述：

  对叔丁基苯甲酰氯 在 4-二甲氨基吡啶 、 bis(1,5-cyclooctadiene)nickel (0) 、 copper(l) iodide 、 三乙胺 、 1,2-双(二环己基磷基)-乙烷 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 16.08h， 生成 ((4-(tert-butyl)phenyl)ethynyl)triisopropylsilane
  参考文献：
  名称：

  酰胺和铜催化的芳基酰胺和烯基酰胺的酰胺脱酰胺交联反应，酰胺转化为炔烃

  摘要：

  公开了酰胺与末端炔烃作为偶联伴侣的镍催化的脱酰胺交叉偶联反应。这种新开发的方法可以将酰胺直接转化为炔烃，并以简单，温和的方式为C（sp2）–C（sp）键的形成提供了一种简便的途径。

  DOI：

  10.1021/acs.orglett.7b01194

文献信息

• Sterically Controlled Late-Stage C–H Alkynylation of Arenes
  作者：Arup Mondal、Hao Chen、Lea Flämig、Philipp Wedi、Manuel van Gemmeren

  DOI：10.1021/jacs.9b10868

  日期：2019.11.27

  Phenylacetylenes are key structural motifs in organic chemistry, which find widespread applications in bioactive molecules, synthetic intermediates, functional materials and reagents. These molecules are typically prepared from pre-functionalized starting materials, e.g. using the Sonogashira coupling, or using directing group-based C-H activation strategies. While highly efficient, these approaches

  苯乙炔是有机化学中的关键结构基序，广泛应用于生物活性分子、合成中间体、功能材料和试剂。这些分子通常由预官能化的起始材料制备，例如使用 Sonogashira 偶联，或使用基于导向基团的 CH 活化策略。虽然效率很高，但这些方法仍然受到它们对特定区域异构体的固有选择性的限制。在此，我们提出了一种基于芳烃限制的非定向 CH 激活的补充方法。该反应主要受空间因素而非电子因素的控制，从而提供了相对于传统方法的互补产品谱。
• Nickel-Catalyzed Decarbonylative Alkynylation of Acyl Fluorides with Terminal Alkynes under Copper-Free Conditions
  作者：Yasushi Nishihara、Qiang Chen、Liyan Fu、Jingwen You

  DOI：10.1055/s-0040-1705954

  日期：2021.9

  Nickel-catalyzed decarbonylative alkynylation of acyl fluorides with terminal silylethynes under copper-free conditions is described. This newly developed method has a wide substrate scope, affording internal silylethynes in moderate to high yields. The formation of 1,3-diynes as homocoupled products and conjugate enones as carbonyl-retentive products were effectively suppressed.

  本文描述了在无铜条件下，镍催化的酰氟与末端硅基乙炔的脱羰基炔基化反应。这种新开发的方法具有广泛的底物范围，产率为中到高。成功抑制了1,3-二炔的同偶联产物和共轭烯酮的羰基保留产物的形成。

• Nickel-Catalyzed Alkynylation of Anisoles via C–O Bond Cleavage
  作者：Mamoru Tobisu、Tsuyoshi Takahira、Akimichi Ohtsuki、Naoto Chatani

  DOI：10.1021/ol503707m

  日期：2015.2.6

  A new cross-coupling reaction has been developed for the introduction of an alkyne moiety to an anisole derivative through C-O bond activation using an NHC ligand. This method has been used for direct alkynylation of a broad range of anisole derivatives and provided rapid access to compounds with potential applications in biological and materials science.
• One-step synthesis of (1-iodovinyl) arenes from trimethylsilyl ethynylarene through iodotrimethylsilane-mediated hydroiodation
  作者：Akihiro H. Sato、Shigenori Mihara、Tetsuo Iwasawa

  DOI：10.1016/j.tetlet.2012.05.004

  日期：2012.7

  One-step access to (1-iodovinyl) arenes from trimethylsilyl ethynylarenes is described. The method is superior to a conventional multi-step approach, and is enhanced by the Sonogashira reaction that provides ready access to a variety of trimethylsilyl ethynylarenes. (C) 2012 Elsevier Ltd. All rights reserved.