ethyl 4-(trimethylsilylethynyl)benzoate | 150969-54-3

• 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: ethyl 4-(trimethylsilylethynyl)benzoate
• 英文别名: 4-ethoxycarbonyl-1-(trimethylsilylethynyl)benzene；ethyl 4-(2-trimethylsilylethynyl)benzoate；Ethyl 4-((trimethylsilyl)ethynyl)benzoate
• CAS: 150969-54-3
• 化学式: C₁₄H₁₈O₂Si
• 分子量: 246.381
• InChiKey: HGAVGUOKLFNPCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 4-(trimethylsilylethynyl)benzoate 在 哌啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 170.37h， 生成 1,4-二(4'-羧基苯)-1,3-丁二炔
  参考文献：
  名称：

  Expanding the Group of Porous Interpenetrated Zr-Organic Frameworks (PIZOFs) with Linkers of Different Lengths

  摘要：

  A Zr-based MOF of the PIZOF type, which consists of two independent and mutually interpenetrating UiO-type frameworks with [Zr6O4(OH)(4)(O2C)(12)] nodes, does not only form with a PEPEP dicarboxylic acid (P = phenylene, E = ethynylene). Also dicarboxylic acids with the shorter PPPP and PEPP spacers were found to give PIZOFs, denoted PPPP-PIZOF and PEPP-PIZOF, respectively. Reducing the spacer length even further to a PEEP segment caused a switchover to the formation of a UiO framework. The hysteresis in the Ar sorption curve of PEPP-PIZOF-1 and the slightly too large amount of combustion residue from PPPP-PIZOF-1 suggest structural defects. These hint at a mismatch between the requirement of the optimal linker length for PIZOF formation and the lengths of the PEPP and PPPP dicarboxylates. Nevertheless, these dicarboxylates prefer the formation of a PIZOF over the formation of a UiO structure. PEPEP-PIZOF-2, PPPP-PIZOF-1, and PEPP-PIZOF-1 are stable in air up to 325, 350, and 300 degrees C, respectively, and have BET surface areas of 2350, 2020, and 1650 m(2) g(-1), respectively. PEPEP-PIZOFs, even those with very hydrophilic oligo(ethylene glycol) side chains on the linkers, are very stable in water and also during drying from a water-wetted state. On the contrary, PEPP-PIZOF-1 and PPPP-PIZOF-1 that had been exposed to water required exchange of water for ethanol before drying to mostly preserve the framework. The results emphasize the importance of differentiating between framework damage caused through hydrolysis in water and through drying from a water-wetted state. The sensitivity of PEPP-PIZOF-1 and PPPP-PIZOF-1 against drying from a water-wetted state may be the consequence of defects. The drying stability of water-wetted PEPEP-PIZOFs lets us suggest that reversible bending of the linkers contributes to the stability of the PEPEP-PIZOFs.

  DOI：

  10.1021/acs.inorgchem.6b01814
• 作为产物：
  描述：

  4-碘苯甲酸 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 硫酸 、 三乙胺 、 三苯基膦 作用下， 生成 ethyl 4-(trimethylsilylethynyl)benzoate
  参考文献：
  名称：

  含有8-（双苯乙炔基）-酯基柔性多元环的氟硼 吡咯类液晶化合物，其制备方法及其应用

  摘要：

  本发明公开了一类含有8‑(双苯乙炔基)‑酯基柔性多元环的氟硼吡咯类液晶染料，其制备方法及应用。本发明以氟化硼络合二吡咯甲川为母体，通过Sonogashira偶联反应在8号位引入双苯乙炔刚性结构，将双环己烷、胆甾醇等柔性多元环利用酯化反应与双苯乙炔基连接，设计合成了一系列8‑(双苯乙炔基)‑酯基柔性多元环的BODIPY类二向色性染料。本发明化合物在二氯甲烷中最大发射波长均集中在525nm左右，呈现绿色荧光，在液晶E7中表现出良好的二向色比及有序参数；本发明的液晶化合物在100‑280℃范围内存在液晶中间相，可用于制造液晶显示产品，尤其是作为宾体染料用于宾主模式液晶显示器；本发明化合物添加至E7液晶并用于宾主显示模式时可提高响应时间，达到快速响应的效果。

  公开号：

  CN109796479B

文献信息

• Cleavage of the Carbon-Carbon Triple Bonds of Arylacetylenes for the Synthesis of Arylnitriles without a Metal Catalyst
  作者：Yuanguang Lin、Qiuling Song

  DOI：10.1002/ejoc.201600438

  日期：2016.6

  Cleavage of the carbon–carbon triple bonds of alkynes was achieved, which led to the synthesis of arylnitriles under transition-metal-free conditions. A vast range of terminal alkyne substrates underwent this reaction to provide the corresponding nitriles in moderate to good yields with good functional group tolerance.

  实现了炔烃的碳-碳三键的裂解，从而在无过渡金属的条件下合成芳腈。大量的末端炔底物经历了这种反应，以中等至良好的产率提供相应的腈，并具有良好的官能团耐受性。
• Cobalt(III)-Catalyzed Direct <i>ortho</i> -Alkenylation of Arylpyrazoles: A Comparative Study on Decarboxylation and Desilylation
  作者：Anil Kumar、Nachimuthu Muniraj、Kandikere Ramaiah Prabhu

  DOI：10.1002/ejoc.201900270

  日期：2019.4.30

  A comparative study on Co-III-catalyzed direct C-H bond alkenylation of 1-phenylpyrazole derivatives with alkynyl carboxylic acids and arylalkynylsilanes under redox-neutral conditions has been disclosed. These methods show excellent selectivity with good to excellent yields. Trimethylsilylacetylene has been utilized as a vinyl source to obtain the corresponding styrene derivatives. The major differences

  已经公开了在氧化还原中性条件下 Co-III 催化的 1-苯基吡唑衍生物与炔基羧酸和芳基炔基硅烷的直接 CH 键烯基化的比较研究。这些方法显示出优异的选择性和良好的收率。三甲基甲硅烷基乙炔已被用作乙烯基来源以获得相应的苯乙烯衍生物。这两个反应之间的主要区别在于脱羧反应在碱添加剂存在下进行，而脱甲硅烷基化在酸添加剂存在下进行。开发的方法与各种功能组兼容。
• Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization
  作者：Kenji Sugimoto、Shuto Kosuge、Takae Sugita、Yuka Miura、Kiyoshi Tsuge、Yuji Matsuya

  DOI：10.1021/acs.orglett.1c01171

  日期：2021.5.21

  A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate;

  报道了一种金（I）自动串联催化方案，用于通过一锅氮杂-烯炔复分解/6π-电环化序列，以高度区域选择性的方式从相应的亚胺衍生物从头合成密集取代的吡唑啉和二氢吡啶。亚胺氮原子上的取代基可以完美地控制来自关键的1-氮杂丁二烯中间体的反应路径；因此，氨基甲酸酯通过α，β-不饱和6的6π-电环化转化为吡唑啉，而芳基亚胺通过3-氮杂己三烯的6π-电环化提供二氢吡啶。
• Carboxylation of alkynylsilanes with carbon dioxide mediated by cesium fluoride in DMSO
  作者：Misato Yonemoto-Kobayashi、Kiyofumi Inamoto、Yoshiyuki Tanaka、Yoshinori Kondo

  DOI：10.1039/c3ob40760h

  日期：——

  The facile syntheses of a variety functionalized propiolic acids were achieved by carboxylation of alkynylsilanes with carbon dioxide mediated by cesium fluoride under ambient conditions.

  通过环境条件下的铯氟化物介导，成功实现了烷炔基硅烷与二氧化碳的羧基化反应，便捷合成了一系列官能化的丙炔酸。
• From Propargylic Alcohols to Substituted Thiochromenes: <i>gem</i>-Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation
  作者：Noelia Velasco、Anisley Suárez、Fernando Martínez-Lara、Manuel Ángel Fernández-Rodríguez、Roberto Sanz、Samuel Suárez-Pantiga

  DOI：10.1021/acs.joc.1c00333

  日期：2021.5.21

  6-endo-dig cyclization of S-aryl propargyl sulfides to afford 2H-thiochromenes. The substitution at the propargylic position plays a crucial role in allowing intramolecular silver-catalyzed alkyne hydroarylation and N-iodosuccinimide-promoted iodoarylation. Additionally, a PTSA-catalyzed thiolation reaction of propargylic alcohols was developed to synthesize the required tertiary S-aryl propargyl ethers. The

  这部作品描述了6-内-挖的环小号芳炔硫化物，提供2 ^ h -thiochromenes。炔丙基位置的取代在允许分子内银催化的炔烃氢化芳基化和N-碘代琥珀酰亚胺促进的碘芳基化中起着至关重要的作用。此外，还开发了 PTSA 催化的炔丙醇硫醇化反应，以合成所需的叔S-芳基炔丙基醚。通过合成视黄酸受体拮抗剂 AGN194310 证明了合并这两种方法的适用性。

表征谱图