trimethyl[(2,4,6-triisopropylphenyl)ethynyl]silane | 1363568-76-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: trimethyl[(2,4,6-triisopropylphenyl)ethynyl]silane
• 英文别名: Trimethyl-[2-[2,4,6-tri(propan-2-yl)phenyl]ethynyl]silane
• CAS: 1363568-76-6
• 化学式: C₂₀H₃₂Si
• 分子量: 300.56
• InChiKey: OXWWLHMBJQTVOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-溴-1,3,5-三异丙苯 、 三甲基乙炔基硅 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以76 %的产率得到trimethyl[(2,4,6-triisopropylphenyl)ethynyl]silane
  参考文献：
  名称：

  大空间位阻炔基保护的 Au22 纳米团簇的合成和力致变色响应

  摘要：

  在还原条件下通过自组装制备了大位阻炔基保护的中性金纳米簇[Au 22 L 14 ] ( 1 ) (L = 2,4,6-三(异丙基)-苯乙炔)。单晶X射线衍射表明，该分子结构含有多面体Au 18内核，该内核由两个六角双锥体和两个以Au原子为顶点的三棱锥体组成。四个钉状 RC = C–Au–C = CR（R = 2,4,6-三（异丙基）-苯基）基序位于 Au 18核心周围，进一步构建了簇1的完整 Au 22核心结构。Au 22核心由 14 个乙炔配体和 42 个大异丙基稳定。观察到固态Au 22纳米团簇在近红外区域发射，发射强度集中在967 nm，计算研究表明磷光发射归因于以金属团簇为中心的过渡，以苯乙炔为中心的过渡。 IL 和 LMCT 状态从苯乙炔到金属中心。具有长范围发射寿命的大斯托克斯位移表明发射可能源自三重态起源。有趣的是，在机械力的刺激下，1表现出显着的发光蓝移响应。

  DOI：

  10.1021/acs.organomet.3c00431

文献信息

• A Guide to Sonogashira Cross-Coupling Reactions: The Influence of Substituents in Aryl Bromides, Acetylenes, and Phosphines
  作者：Marc Schilz、Herbert Plenio

  DOI：10.1021/jo202644g

  日期：2012.3.16

  The conversion time data for 168 different Pd/Cu-catalyzed Sonogashira cross-coupling reactions of five arylacetylenes (phenylacetylene; 1-ethynyl-2-ethylbenzene; 1-ethynyl-2,4,6-R-3-benzene (R = Me, Et, i-Pr)) and Me3SiCCH with seven aryl bromides (three 2-R-bromobenzenes (R = Me, Et, i-Pr); 2,6-Me-2-bromobenzene and three 2,4,6-R-3-bromobenzenes (R = Me, Et, i-Pr)) with four different phosphines (P-t-Bu-3, t-Bu2PCy, t-BuPCy2, PCy3) were determined using quantitative gas chromatography. The stereoelectronic properties of the substituents in the aryl bromides, acetylenes, and phosphines were correlated with the performance in Sonogashira reactions. It was found that the nature of the most active Pd/PR3 complex for a Sonogashira transformation is primarily determined by the steric bulk of the acetylene; ideal catalysts are: Pd/P-t-Bu-3 or Pd/t-Bu2PCy for sterically undemanding phenylacetylene, Pd/t-BuPCy2 for 2- and 2,6-substituted arylacetylenes or Me3SiCCH and Pd/PCy3 for extremely bulky acetylenes and aryl bromides. Electron-rich and sterically demanding aryl bromides with substituents in the 2- or the 2,6-position require larger amounts of catalyst than 4-substituted aryl bromides. The synthesis of tolanes with bulky groups at one of the two aryl rings is best done by placing the steric bulk at the arylacetylene, which is also the best place for electron-withdrawing substituents.