3-硝基-5-苯基吡啶 | 123792-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3-硝基-5-苯基吡啶
• 英文名称: 3-nitro-5-phenylpyridine
• CAS: 123792-62-1
• 化学式: C₁₁H₈N₂O₂
• 分子量: 200.197
• InChiKey: LXBLPKWPBMJMOW-UHFFFAOYSA-N

物化性质

• 熔点：
  92.5-93.5 °C(Solv: hexane (110-54-3))
• 沸点：
  353.1±30.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• 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：

  3-硝基-5-苯基吡啶 在 4-氨基-1,2,4-三氮唑 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以66%的产率得到2-amino-3-phenyl-5-nitropyridine
  参考文献：
  名称：

  Selective vicarious nucleophilic amination of 3-nitropyridines

  摘要：

  通过代亲核取代反应，九种 3-硝基吡啶化合物和 4-硝基异喹啉在 6 位（4-硝基异喹啉在 1 位）被胺化。使用了两种胺化试剂：羟胺和 4-氨基-1,2,4-三唑。产率从中等到良好不等。使用羟胺可以直接获得几乎纯净的产品，而 4-氨基-1,2,4-三唑则可以为某些底物提供更好的胺化产品收率。由此，我们获得了一种制备 3-或 4-取代的 2-氨基-5-硝基吡啶的通用方法。

  DOI：

  10.1039/b008660f
• 作为产物：
  描述：

  4-(2-苯基乙烯基)-吗啉 、 5-硝基嘧啶 以 乙醇 为溶剂， 反应 24.0h， 以28%的产率得到3-硝基-5-苯基吡啶
  参考文献：
  名称：

  5-硝基嘧啶与烯胺的电子反需求狄尔斯-阿尔德反应。3-硝基吡啶衍生物的合成

  摘要：

  已经研究了环状和非环状烯胺与5-硝基嘧啶的反应。许多烯胺以反电子需求的狄尔斯-阿尔德反应进行反应，导致形成3-硝基吡啶。还发现N，S-乙烯酮缩醛与5-硝基嘧啶反应。将讨论该反应的机理。

  DOI：

  10.1016/s0040-4020(01)80099-5

文献信息

• An Alternative Synthetic Approach to 3-Alkylated/Arylated 5-Nitropyridines
  作者：Song Thi Le、Haruyasu Asahara、Nagatoshi Nishiwaki

  DOI：10.1021/acs.joc.5b01391

  日期：2015.9.4

  An alternative method for the synthesis of 3-alkylated/arylated 5-nitropyridines was developed involving a three-component ring transformation of 3,5-dinitro-2-pyridone on treatment with aldehyde in the presence of ammonium acetate. This method facilitates the modification of the substituent at the 3-position by changing the precursor aldehyde. The use of solid ammonium acetate instead of ammonia as

  已开发出另一种合成3-烷基化/芳基化5-硝基吡啶的方法，该方法涉及在乙酸铵存在下用醛处理3,5-二硝基-2-吡啶酮的三组分环转化。该方法通过改变前体醛促进了3-位取代基的修饰。使用固体乙酸铵代替氨作为氮源使合成方法更加实用和用户友好。
• C–H Arylation of Pyridines: High Regioselectivity as a Consequence of the Electronic Character of C–H Bonds and Heteroarene Ring
  作者：Pengfei Guo、Jung Min Joo、Souvik Rakshit、Dalibor Sames

  DOI：10.1021/ja206022p

  日期：2011.10.19

  We report a new catalytic protocol for highly selective C-H arylation of pyridines containing common and synthetically versatile electron-withdrawing substituents (NO(2), CN, F and Cl). The new protocol expands the scope of catalytic azine functionalization as the excellent regioselectivity at the 3- and 4-positions well complements the existing methods for C-H arylation and Ir-catalyzed borylation, as well as classical functionalization of pyridines. Another important feature of the new method is its flexibility to adapt to challenging substrates by a simple modification of the carboxylic acid ligand or the use of silver salts. The regioselectivity can be rationalized on the basis of the key electronic effects (repulsion between the nitrogen lone pair and polarized C-Pd bond at C2-/C6-positions and acidity of the C-H bond) in combination with steric effects (sensitivity to bulky substituents).
• MARCELIS, A. T. M.;VAN, DER PLAS H. C., TETRAHEDRON, 45,(1989) N, C. 2693-2702
  作者：MARCELIS, A. T. M.、VAN, DER PLAS H. C.

  DOI：——

  日期：——
• Inverse electron demand diels-alder reactions of 5-nitropyrimidine with enamines. synthesis of 3-nitropyridine derivatives
  作者：Antonius T.M. Marcelis、Henk C. Van Der Plas

  DOI：10.1016/s0040-4020(01)80099-5

  日期：1989.1

  The reaction of cyclic and non-cyclic enamines with 5-nitropyrimidine has been studied. Many enamines react in an inverse electron-demand Diels-Alder reaction, leading to the formation of 3-nitropyridines. N,S-ketene acetals were also found to react with 5-nitropyrimidine. The mechanism of the reaction will be discussed.

  已经研究了环状和非环状烯胺与5-硝基嘧啶的反应。许多烯胺以反电子需求的狄尔斯-阿尔德反应进行反应，导致形成3-硝基吡啶。还发现N，S-乙烯酮缩醛与5-硝基嘧啶反应。将讨论该反应的机理。
• Selective vicarious nucleophilic amination of 3-nitropyridines
  作者：Jan M. Bakke、Harald Svensen、Raffaela Trevisan

  DOI：10.1039/b008660f

  日期：——

  Nine 3-nitropyridine compounds and 4-nitroisoquinoline have been aminated in the 6-position (for 4-nitroisoquinoline in the 1-position) by vicarious nucleophilic substitution reactions. Two amination reagents were used, hydroxylamine and 4-amino-1,2,4-triazole. The yields were from moderate to good. Use of hydroxylamine gave an easy work-up procedure by which almost pure product was obtained directly, but 4-amino-1,2,4-triazole gave better yields of the aminated product for some of the substrates. By this, a general method for the preparation of 3- or 4-substituted-2-amino-5-nitropyridines was obtained.

  通过代亲核取代反应，九种 3-硝基吡啶化合物和 4-硝基异喹啉在 6 位（4-硝基异喹啉在 1 位）被胺化。使用了两种胺化试剂：羟胺和 4-氨基-1,2,4-三唑。产率从中等到良好不等。使用羟胺可以直接获得几乎纯净的产品，而 4-氨基-1,2,4-三唑则可以为某些底物提供更好的胺化产品收率。由此，我们获得了一种制备 3-或 4-取代的 2-氨基-5-硝基吡啶的通用方法。

表征谱图