[(2-乙基苯基)乙炔基](三甲基)硅烷 | 492448-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [(2-乙基苯基)乙炔基](三甲基)硅烷
• 英文名称: [2-(2-ethylphenyl)ethynyl]trimethylsilane
• 英文别名: ((2-ethylphenyl)ethynyl)trimethylsilane；2-ethyl-1-(2-trimethylsilyl-1-ethynyl)benzene；Silane, [(2-ethylphenyl)ethynyl]trimethyl-(9CI)；2-(2-ethylphenyl)ethynyl-trimethylsilane
• CAS: 492448-53-0
• 化学式: C₁₃H₁₈Si
• 分子量: 202.371
• InChiKey: NYFPAGHUQRIQDX-UHFFFAOYSA-N

物化性质

• 沸点：
  248.4±23.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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-乙基苯基)乙炔基](三甲基)硅烷 在 potassium fluoride 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以80%的产率得到1-乙基-2-乙炔苯
  参考文献：
  名称：

  Rational Design of 4-Aryl-1,2,3-Triazoles for Indoleamine 2,3-Dioxygenase 1 Inhibition

  摘要：

  Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used computational structure-based methods to design more potent ligands. This approach yielded highly efficient low molecular weight inhibitors, the most active being of nanomolar potency both in an enzymatic and in a cellular assay, while showing no cellular toxicity and a high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.

  DOI：

  10.1021/jm300260v
• 作为产物：
  描述：

  2-溴乙苯 、 三甲基乙炔基硅 在 sodium tetrachloropalladate 、 copper(l) iodide 、 叔丁基二环己基膦 、 二异丙胺 作用下， 以88%的产率得到[(2-乙基苯基)乙炔基](三甲基)硅烷
  参考文献：
  名称：

  A Guide to Sonogashira Cross-Coupling Reactions: The Influence of Substituents in Aryl Bromides, Acetylenes, and Phosphines

  摘要：

  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.

  DOI：

  10.1021/jo202644g

文献信息

• Formation of New Alkynyl(phenyl)iodonium Salts and Their Use in the Synthesis of Phenylsulfonyl Indenes and Acetylenes
  作者：A. Koumbis、C. Kyzas、A. Savva、A. Varvoglis

  DOI：10.3390/10101340

  日期：——

  The preparation of phenylsulfonyl indene derivatives and phenylsulfonyl- acetylenes from readily available alkynyl(phenyl)iodonium tetrafluoroborates and triflates was investigated using phenylsulfinate as nucleophile.

  使用苯亚磺酸盐作为亲核试剂研究了从容易获得的炔基（苯基）碘鎓四氟硼酸盐和三氟甲磺酸盐制备苯磺酰基茚衍生物和苯磺酰基-乙炔。
• Microwave-assisted, Copper-free Sonogashira Coupling Between Aryl Halides and Terminal Alkynes Using Recyclable Ionic Liquid and Catalyst
  作者：Dau Xuan Duc、Nguyen Van Quoc

  DOI：10.2174/1570178618666210820101129

  日期：2022.1

  :An efficient method for the Sonogashira coupling reaction between aryl halides and terminalalkynes has been developed. The reaction was performed in ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim][BF4]) under microwave irradiation. High yields ofproducts were obtained in a very short reaction time. Moreover, the medium and catalyst could berecovered and reused three times without

  : 开发了芳基卤化物和末端炔烃之间的 Sonogashira 偶联反应的有效方法。反应在离子液体1-丁基-3-甲基咪唑鎓四氟硼酸盐([Bmim][BF4])中在微波辐射下进行。在非常短的反应时间内获得了高产率的产物。此外，介质和催化剂可以回收和重复使用3次，而反应收率不会显着降低。
• Palladium-catalyzed carboncarbon coupling reactions using aryl Grignards
  作者：Christine Gottardo、Andrea Aguirre

  DOI：10.1016/s0040-4039(02)01538-1

  日期：2002.9

  Coupling reactions using Pd(PPh3)(4) were investigated with a number of electron donating and electron withdrawing substituents. High yields were obtained with both types of substituents. In competitive reactions the electron-withdrawing group -NO2 reacted preferentially over the electron donating groups. When the starting halides were converted to Grignard reagents, high yields were obtained for some hindered electron-withdrawing groups. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.
• Rational Design of 4-Aryl-1,2,3-Triazoles for Indoleamine 2,3-Dioxygenase 1 Inhibition
  作者：Ute F. Röhrig、Somi Reddy Majjigapu、Aurélien Grosdidier、Sylvian Bron、Vincent Stroobant、Luc Pilotte、Didier Colau、Pierre Vogel、Benoît J. Van den Eynde、Vincent Zoete、Olivier Michielin

  DOI：10.1021/jm300260v

  日期：2012.6.14

  Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used computational structure-based methods to design more potent ligands. This approach yielded highly efficient low molecular weight inhibitors, the most active being of nanomolar potency both in an enzymatic and in a cellular assay, while showing no cellular toxicity and a high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.