3-(2-(吡啶-2-基)乙炔基)-5-硝基苯甲腈 | 1031370-96-3

• 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: 3-(2-(吡啶-2-基)乙炔基)-5-硝基苯甲腈
• 英文名称: 3-(2-(pyridin-2-yl)ethynyl)-5-nitrobenzonitrile
• 英文别名: 3-nitro-5-(pyridin-2-ylethynyl)benzonitrile；3-nitro-5-(2-pyridin-2-ylethynyl)benzonitrile
• CAS: 1031370-96-3
• 化学式: C₁₄H₇N₃O₂
• 分子量: 249.228
• InChiKey: SCEZDEAWHINYOD-UHFFFAOYSA-N

物化性质

• 沸点：
  437.6±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-(吡啶-2-基)乙炔基)-5-硝基苯甲腈 在 盐酸 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 0.25h， 生成 3-(2-(pyridin-2-yl)ethynyl)-5-nitrobenzonitrile hydrochloride
  参考文献：
  名称：

  Potent mGluR5 antagonists: Pyridyl and thiazolyl-ethynyl-3,5-disubstituted-phenyl series

  摘要：

  We report the synthesis of four series of 3,5-disubstituted-phenyl ligands targeting the metabotropic glutamate receptor subtype 5: (2-methylthiazol-4-yl)ethynyl (1a-j,), (6-methylpyridin-2-yl)ethynyl (2a-j), (5-methylpyridin-2-yl)ethynyl (3a-j,), and (pyridin-2-yl)ethynyl (4a-j,). The compounds were evaluated for antagonism of glutamate-mediated mobilization of internal calcium in an mGluR5 in vitro assay. All compounds were found to be full antagonists and exhibited low nanomolar to subnanomolar activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.047
• 作为产物：
  描述：

  3-溴-5-硝基苯甲酸 在 bis-triphenylphosphine-palladium(II) chloride 、 ammonium hydroxide 、 copper(l) iodide 、 氯化亚砜 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 3-(2-(吡啶-2-基)乙炔基)-5-硝基苯甲腈
  参考文献：
  名称：

  Potent mGluR5 antagonists: Pyridyl and thiazolyl-ethynyl-3,5-disubstituted-phenyl series

  摘要：

  We report the synthesis of four series of 3,5-disubstituted-phenyl ligands targeting the metabotropic glutamate receptor subtype 5: (2-methylthiazol-4-yl)ethynyl (1a-j,), (6-methylpyridin-2-yl)ethynyl (2a-j), (5-methylpyridin-2-yl)ethynyl (3a-j,), and (pyridin-2-yl)ethynyl (4a-j,). The compounds were evaluated for antagonism of glutamate-mediated mobilization of internal calcium in an mGluR5 in vitro assay. All compounds were found to be full antagonists and exhibited low nanomolar to subnanomolar activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.047

文献信息

• Multiple Approaches to the In Situ Generation of Anhydrous Tetraalkylammonium Fluoride Salts for S_NAr Fluorination Reactions
  作者：Megan A. Cismesia、Sarah J. Ryan、Douglas C. Bland、Melanie S. Sanford

  DOI：10.1021/acs.joc.7b00481

  日期：2017.5.19

  focuses on the development of practical approaches to the in situ generation of anhydrous fluoride salts for applications in nucleophilic aromatic substitution (SNAr) reactions. We report herein that a variety of combinations of inexpensive nucleophiles (e.g., tetraalkylammonium cyanide and phenoxide salts) and fluorine-containing electrophiles (e.g., acid fluoride, fluoroformate, benzenesulfonyl fluoride

  本文主要讨论的实际方法的原位生成无水氟化氢的盐的发展在亲核芳族取代（S应用Ñ AR）的反应。我们在此报告，廉价的亲核试剂（例如，四烷基氰化铵和酚盐）和含氟亲电试剂（例如，酰基氟，氟甲酸酯，苯磺酰氟和芳基氟磺酸酯衍生物）的多种组合对这种转化有效。最终，我们证明了2,6-二甲基苯氧基四甲基铵和硫酰氟（SO 2 F 2）的组合是制备无水四甲基氟化铵的一种特别实用的方法。此过程适用于S NAr氟化一系列电子不足的芳基和杂芳基氯化物以及硝基芳烃。
• Effect of Leaving Group Substituents on the Microfluidic Synthesis of [18F]3-Fluoro-5-[(pyridin-3-yl)ethynyl]benzonitrile ([18F]FPEB)
  作者：George W. Kabalka、Thomas M. Moore、Murthy R. Akula、Lee Collier、Gilles Tamagnan、Caroline Papin、David Alagille

  DOI：10.3987/com-16-s(s)49

  日期：——

  A commercial microfluidic reactor system has been used to synthesize the mGLUR5 receptor imaging agent [F-18]FPEB. To study the effect of leaving group substituents on the synthesis of the desired compound, the chloro-, bromo-, iodo-, and nitro-substituted precursors for FPEB were evaluated. Precursor concentrations of 4 - 10 mg/mL were evaluated in various solvents, with temperature ranges between 120 and 220 degrees C, and total processing times of less than five minutes. Optimized incorporation yields ranged from 5% to 69.4% depending on the precursor used.
• Potent mGluR5 antagonists: Pyridyl and thiazolyl-ethynyl-3,5-disubstituted-phenyl series
  作者：David Alagille、Herve DaCosta、Yelin Chen、Kamondanai Hemstapat、Alice Rodriguez、Ronald M. Baldwin、Jeffrey P. Conn、Gilles D. Tamagnan

  DOI：10.1016/j.bmcl.2011.04.047

  日期：2011.6

  We report the synthesis of four series of 3,5-disubstituted-phenyl ligands targeting the metabotropic glutamate receptor subtype 5: (2-methylthiazol-4-yl)ethynyl (1a-j,), (6-methylpyridin-2-yl)ethynyl (2a-j), (5-methylpyridin-2-yl)ethynyl (3a-j,), and (pyridin-2-yl)ethynyl (4a-j,). The compounds were evaluated for antagonism of glutamate-mediated mobilization of internal calcium in an mGluR5 in vitro assay. All compounds were found to be full antagonists and exhibited low nanomolar to subnanomolar activity. (C) 2011 Elsevier Ltd. All rights reserved.