2-乙炔基-5-硝基吡啶 | 452333-53-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 2-乙炔基-5-硝基吡啶
• 英文名称: 2-ethynyl-5-nitropyridine
• CAS: 452333-53-8
• 化学式: C₇H₄N₂O₂
• 分子量: 148.121
• InChiKey: LGPWDEKBZZUODK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-乙炔基-5-硝基吡啶 在 硫酸 、 mercury(II) diacetate 、 水 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以48%的产率得到1-(5-硝基吡啶-2-基)乙酮
  参考文献：
  名称：

  Nitropyridines: X. Palladium-catalyzed cross-coupling of 2-bromo-5-nitropyridine with terminal acetylenes

  摘要：

  Substituted 5-nitro-2-ethynylpyridines were synthesized by the Sonogashira reaction of 2-bromo-5-5-nitropyridine with terminal acetylenes. Desilylation, oxidative decarbonylation, and the retro-Favorskii reaction of the cross-coupling products of 2-bromo-5-nitropyridine with trimethylsilylacetylene, prop-2-ynyl alcohol, and 2-methylbut-3-yn-2-ol, respectively, gave 2-ethynyl-5-nitropyridine. The hydration of 2-ethynyl-5-nitropyridine and 5-nitro-2-(phenylethynyl)pyridine according to Kucherov afforded 2-acetyl-5-nitropyridine and 5-nitro-2-phenacylpyridine, respectively.

  DOI：

  10.1134/s1070428010120109
• 作为产物：
  描述：

  2-溴-5-硝基吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium acetate 、 potassium hydroxide 作用下， 以 乙腈 、 苯 为溶剂， 反应 3.0h， 生成 2-乙炔基-5-硝基吡啶
  参考文献：
  名称：

  Nitropyridines: X. Palladium-catalyzed cross-coupling of 2-bromo-5-nitropyridine with terminal acetylenes

  摘要：

  Substituted 5-nitro-2-ethynylpyridines were synthesized by the Sonogashira reaction of 2-bromo-5-5-nitropyridine with terminal acetylenes. Desilylation, oxidative decarbonylation, and the retro-Favorskii reaction of the cross-coupling products of 2-bromo-5-nitropyridine with trimethylsilylacetylene, prop-2-ynyl alcohol, and 2-methylbut-3-yn-2-ol, respectively, gave 2-ethynyl-5-nitropyridine. The hydration of 2-ethynyl-5-nitropyridine and 5-nitro-2-(phenylethynyl)pyridine according to Kucherov afforded 2-acetyl-5-nitropyridine and 5-nitro-2-phenacylpyridine, respectively.

  DOI：

  10.1134/s1070428010120109

文献信息

• Modulators of LXR
  申请人：Bayne D. Christopher

  公开号：US20050080111A1

  公开（公告）日：2005-04-14

  Compounds of the invention, such as compounds of formula (I): where n, m, A, B, R 1 , R 2 , R 3 , R 4 and R 5 are defined herein, are useful as modulators of the activity of liver X receptors. Pharmaceutical compositions containing the compounds and methods of using the compounds are also disclosed.

  本发明的化合物，例如式（I）的化合物：其中n，m，A，B，R1，R2，R3，R4和R5如本文所定义，可用作肝X受体活性的调节剂。还公开了含有这些化合物的药物组合物和使用这些化合物的方法。
• Synthesis of Sugar-Derived Triazole- and Pyridine-Based Metal Complex Ligands
  作者：Thomas Ziegler、Jochen Kraft、Daniel Schmollinger、Jakob Maudrich

  DOI：10.1055/s-0034-1379473

  日期：——

  for metals were prepared by copper-catalyzed coupling (CLICK reaction) of 2-ethynylpridine, 2-ethynyl-5-nitropyridine, 2-ethynylquinoline, and 2,6-diethynylpyridine with 12 protected glycosyl azides in the gluco and galacto series and 2 benzyl azides. The 1,2,3-triazole-linked glycoconjugates prepared were used as ligands for the copper-catalyzed addition of phenylacetylene to N-benzylideneaniline to

  摘要 通过2-乙炔基吡啶，2-乙炔基-5-硝基吡啶，2-乙炔基喹啉和2,6-二乙炔吡啶与十二种保护的糖基叠氮化物的铜催化偶联（CLICK反应），制备了一系列30种金属的双齿和三齿配体在葡萄糖和半乳糖系列中和2个苄基叠氮化物。制备的1,2,3-三唑连接的糖缀合物用作配体，用于铜催化的苯乙炔加成到N-亚苄基苯胺上，得到手性N-（1,3-二苯基丙-2-炔-1-基）苯胺。 通过2-乙炔基吡啶，2-乙炔基-5-硝基吡啶，2-乙炔基喹啉和2,6-二乙炔吡啶与十二种保护的糖基叠氮化物的铜催化偶联（CLICK反应），制备了一系列30种金属的双齿和三齿配体在葡萄糖和半乳糖系列中和2个苄基叠氮化物。制备的1,2,3-三唑连接的糖缀合物用作配体，用于铜催化的苯乙炔加成到N-亚苄基苯胺上，得到手性N-（1,3-二苯基丙-2-炔-1-基）苯胺。
• Metal-free Synthesis of 2-Alkenyl/Alkynyl-5-nitropyridines Using a Three-component Ring Transformation
  作者：Song Thi Le、Haruyasu Asahara、Nagatoshi Nishiwaki

  DOI：10.1246/cl.150045

  日期：2015.6.5

  A metal-free, facile, and efficient protoco lf or synthesizing a series of 2-alkenyl/alkynyl-5-nitropyridines was developed by using a three-component ring transformation of 1-methyl-3,5-dinitro-2-pyridone with α,β-unsaturated ketones and ammonium acetate. As 2-alkenyl/alkynyl-5-nitropyridines are not easily prepared by Heck or Sonogashira reactions, this method will be a supplementary to these reactions

  通过使用 1-甲基-3,5-二硝基-2-吡啶酮的三组分环转化，开发了一种不含金属、简便且高效的方案或合成一系列 2-烯基/炔基-5-硝基吡啶。 α,β-不饱和酮和醋酸铵。由于 Heck 或 Sonogashira 反应不容易制备 2-烯基/炔基-5-硝基吡啶，因此该方法将是这些反应的补充。
• Modulators Of Nuclear Receptors
  申请人：Bayne Christopher D.

  公开号：US20080119488A1

  公开（公告）日：2008-05-22

  Compounds of the invention, such as compounds of formula (I), where n, m, A, R1, R2, R3, R4 and R5 are defined herein, are useful as modulators of the activity of liver X receptors. Pharmaceutical compositions containing the compounds and methods of using the compounds are also disclosed.

  本发明的化合物，例如式（I）中的化合物，其中n，m，A，R1，R2，R3，R4和R5在此定义，可用作肝X受体活性调节剂。还公开了含有该化合物的制药组合物和使用该化合物的方法。
• Facile synthesis of chelating bisphosphine oxides and bisphosphines via palladium-catalyzed bishydrophosphinylation reactions
  作者：Aberdeen Allen、Ling Ma、Wenbin Lin

  DOI：10.1016/s0040-4039(02)00609-3

  日期：2002.5

  A series of functional bisphosphosphine oxides were synthesized in good yields via new Pd-catalyzed bis-hydrophosphinylation reactions of terminal alkynes and diphenylphosphine oxide. The resulting bisphosphine oxides were reduced to their corresponding bisphosphines in quantitative yields via a Ti((OPr)-Pr-i)(4)-mediated process. (C) 2002 Elsevier Science Ltd. All rights reserved.