2-(Trimethylsilylethynyl)quinoxaline | 189629-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(Trimethylsilylethynyl)quinoxaline
• 英文别名: Quinoxaline, 2-[(trimethylsilyl)ethynyl]-；trimethyl(2-quinoxalin-2-ylethynyl)silane
• CAS: 189629-50-3
• 化学式: C₁₃H₁₄N₂Si
• 分子量: 226.353
• InChiKey: VNCUUDZWWXLIKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(Trimethylsilylethynyl)quinoxaline 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以88%的产率得到2-乙炔基喹喔啉
  参考文献：
  名称：

  Synthesis of thieno[2,3-b]quinoxalines from 2-haloquinoxalines

  摘要：

  通过钯（0）催化 2-卤代喹喔啉与炔烃的偶联，在生成的 2-炔基喹喔啉中加入一摩尔当量的溴，然后将生成的二溴化物与三硫代碳酸二钾反应，生成噻吩并[2,3-b]喹喔啉。

  DOI：

  10.1039/b008459j
• 作为产物：
  描述：

  2-氯喹恶啉 、 三甲基乙炔基硅 在 copper(l) iodide 、 palladium diacetate 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 以54%的产率得到2-(Trimethylsilylethynyl)quinoxaline
  参考文献：
  名称：

  Synthesis of thieno[2,3-b]quinoxalines from 2-haloquinoxalines

  摘要：

  通过钯（0）催化 2-卤代喹喔啉与炔烃的偶联，在生成的 2-炔基喹喔啉中加入一摩尔当量的溴，然后将生成的二溴化物与三硫代碳酸二钾反应，生成噻吩并[2,3-b]喹喔啉。

  DOI：

  10.1039/b008459j

文献信息

• Microwave-assisted in situ deprotection and ω-methoxylation of TMS-protected aryl alkynes
  作者：Jenny Wettergren、Alexander B.E. Minidis

  DOI：10.1016/j.tetlet.2003.08.059

  日期：2003.10

  Using microwave technology, rapid omega-methoxylation of aryl alkynes is possible. (C) 2003 Elsevier Ltd. All rights reserved.
• Efficient Pd-Catalyzed Coupling of Tautomerizable Heterocycles with Terminal Alkynes via C−OH Bond Activation Using PyBrOP
  作者：Ce Shi、Courtney C. Aldrich

  DOI：10.1021/ol100657n

  日期：2010.5.21

  The direct alkynylation of tautomerizable heterocycles is described via a two-step process involving in situ C OH activation with bromotripyrrolidinophosphonium hexafluorophosphate (PyBrOP) followed by Sonogashira coupling with a wide range of alkyl or aryl terminal alkynes using a copper-free system employing PdCl2(CH3CN)(2) and 2-(dicyclohexylphosphino)biphenyl.
• Dinsmore, Andrew; Birks, Jacqueline H.; Garner, C. David, Journal of the Chemical Society. Perkin transactions I, 1997, # 6, p. 801 - 807
  作者：Dinsmore, Andrew、Birks, Jacqueline H.、Garner, C. David、Joule, John A.

  DOI：——

  日期：——
• Rapid Discovery of a Novel Series of Abl Kinase Inhibitors by Application of an Integrated Microfluidic Synthesis and Screening Platform
  作者：Bimbisar Desai、Karen Dixon、Elizabeth Farrant、Qixing Feng、Karl R. Gibson、Willem P. van Hoorn、James Mills、Trevor Morgan、David M. Parry、Manoj K. Ramjee、Christopher N. Selway、Gary J. Tarver、Gavin Whitlock、Adrian G. Wright

  DOI：10.1021/jm400099d

  日期：2013.4.11

  Drug discovery faces economic and scientific imperatives to deliver lead molecules rapidly and efficiently. Using traditional paradigms the molecular design, synthesis, and screening loops enforce a significant time delay leading to inefficient use of data in the iterative molecular design process. Here, we report the application of a flow technology platform integrating the key elements of structure activity relationship (SAR) generation to the discovery of novel Abl kinase inhibitors. The platform utilizes flow chemistry for rapid in-line synthesis, automated purification, and analysis coupled with bioassay. The combination of activity prediction using Random-Forest regression with chemical space sampling algorithms allows the construction of an activity model that refines itself after every iteration of synthesis and biological result. Within just 21 compounds, the automated process identified a novel template and hinge binding motif with pIC(50) > 8 against Abl kinase - both wild type and clinically relevant mutants. Integrated microfluidic synthesis and screening coupled with machine learning design have the potential to greatly reduce the time and cost of drug discovery within the hit-to-lead and lead optimization phases.
• Synthesis of thieno[2,3-b]quinoxalines from 2-haloquinoxalines
  作者：Montserrat Armengol、John A. Joule

  DOI：10.1039/b008459j

  日期：——

  The palladium(0)-catalysed coupling of 2-haloquinoxalines with alkynes, addition of one mol equivalent of bromine to the 2-alkynylquinoxalines thus produced and then reaction of the resulting dibromides with dipotassium trithiocarbonate produces thieno[2,3-b]quinoxalines.

  通过钯（0）催化 2-卤代喹喔啉与炔烃的偶联，在生成的 2-炔基喹喔啉中加入一摩尔当量的溴，然后将生成的二溴化物与三硫代碳酸二钾反应，生成噻吩并[2,3-b]喹喔啉。