2-(4-nitrophenyl)pyridine 1-oxide | 84794-09-2

• 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
• 英文名称: 2-(4-nitrophenyl)pyridine 1-oxide
• 英文别名: 2-(4-nitrophenyl)pyridine-1-oxide；2-(p-nitrophenyl)pyridine N-oxide；2-(4-nitro-phenyl)-pyridine-1-oxide；2-(4-Nitro-phenyl)-pyridin-1-oxid；2-<4-Nitro-phenyl>-pyridin-N-oxid；2-(4-Nitrophenyl)-1-oxidopyridin-1-ium
• CAS: 84794-09-2
• 化学式: C₁₁H₈N₂O₃
• 分子量: 216.196
• InChiKey: FDXMJJKVRCVSQY-UHFFFAOYSA-N

物化性质

• 熔点：
  212-214 °C(Solv: ethanol (64-17-5))
• 沸点：
  485.1±20.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 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：
  71.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-nitrophenyl)pyridine 1-oxide 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium acetate 、 硫酸二甲酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 6-(4-Amino-phenyl)-pyridine-2-carboxylic acid
  参考文献：
  名称：

  Antiallergic agents. 2. N-(1H-Tetrazol-5-yl)-6-phenyl-2-pyridinecarboxamides

  摘要：

  A new series of N-(1H-tetrazol-5-yl)-6-phenyl-2-pyridinecarboxamides was prepared to determine the effects of substituents on the benzene and pyridine rings on antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) assay after oral administration. One member of this series, N-(1H-tetrazol-5-yl)-4-methyl-6-[4-(methylamino)-phenyl]-2- pyridinecarboxamide (231), has an ED50 value of 0.8 mg/kg po and is 85 times more potent than disodium cromoglycate (DSCG) on intravenous administration. Further evaluation of 231 as a clinically useful antiallergic agent is in progress.

  DOI：

  10.1021/jm00364a026
• 作为产物：
  描述：

  2-(4-硝基苯基)吡啶 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 20.0h， 生成 2-(4-nitrophenyl)pyridine 1-oxide
  参考文献：
  名称：

  Antiallergic agents. 2. N-(1H-Tetrazol-5-yl)-6-phenyl-2-pyridinecarboxamides

  摘要：

  A new series of N-(1H-tetrazol-5-yl)-6-phenyl-2-pyridinecarboxamides was prepared to determine the effects of substituents on the benzene and pyridine rings on antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) assay after oral administration. One member of this series, N-(1H-tetrazol-5-yl)-4-methyl-6-[4-(methylamino)-phenyl]-2- pyridinecarboxamide (231), has an ED50 value of 0.8 mg/kg po and is 85 times more potent than disodium cromoglycate (DSCG) on intravenous administration. Further evaluation of 231 as a clinically useful antiallergic agent is in progress.

  DOI：

  10.1021/jm00364a026

文献信息

• Ascorbic Acid as an Initiator for the Direct CH Arylation of (Hetero)arenes with Anilines Nitrosated In Situ
  作者：Fernando Pinacho Crisóstomo、Tomás Martín、Romen Carrillo

  DOI：10.1002/anie.201309761

  日期：2014.2.17

  direct CH arylation of (hetero)arenes. Starting from an aniline, the corresponding arenediazonium ion is generated in situ and immediately reduced by vitamin C to an aryl radical that undergoes a homolytic aromatic substitution with a (hetero)arene. Notably, neither heating nor irradiation is required. This procedure is mild, operationally simple, and constitutes a greener approach to arylation.

  抗坏血酸（维生素C）已被用作（杂）芳烃的无金属直接CH芳基化反应中的自由基引发剂。从苯胺开始，相应的苯二氮杂鎓离子在原位生成，并立即被维生素C还原为芳基，该芳基经历了（杂）芳烃的均相芳族取代。值得注意的是，既不需要加热也不需要辐照。该过程是温和的，操作简单的，并且构成了芳构化的绿色方法。
• Pd-Catalyzed Decarboxylative Cross-Coupling of 2-Carboxyazine<i>N</i>-Oxides with Various (Hetero)aryl Halides
  作者：Jean-Baptiste Rouchet、Cédric Schneider、Cédric Spitz、Johan Lefèvre、George Dupas、Corinne Fruit、Christophe Hoarau

  DOI：10.1002/chem.201304773

  日期：2014.3.24

  Decarboxylative cross‐coupling reactions of substituted 2‐carboxyazine N‐oxides, with a variety of (hetero)aryl halides, by bimetallic Pd0/CuI and Pd0/AgI catalysis are reported. Two possible pathways, a conventional bimetallic‐catalyzed decarboxylative arylation, as well as a protodecarboxylative/direct CH arylation sequence have been considered. These methods provide the first general decarboxylative

  据报道，通过双金属Pd 0 / Cu I和Pd 0 / Ag I催化，取代的2-羧嗪N-氧化物与各种（杂）芳基卤化物发生脱羧交叉偶联反应。两种可能的途径，传统的双金属催化的芳基化脱羧，以及一个protodecarboxylative /直接ç  ħ芳基化序列已被考虑。这些方法为2-羧嗪系列提供了第一个通用的脱羧芳基化方法。
• Activation of Unstrained Ketone C(O)–C Bond: 1,2-Nucleophilic Addition Followed by β-Carbon Elimination Strategy
  作者：Qiang Li、Yiwen Xu、Yang Long、Sun Li、Buyi Xu、Ying Xia、Xiangge Zhou

  DOI：10.1021/acscatal.3c01602

  日期：2023.6.16

  moiety followed by β-C elimination strategy was less studied. Here a palladium-catalyzed C–C bond activation of an unstrained ketone enabled by a removable directing group through β-C elimination to synthesize 2-arylpyridine is described. The protocol features wide substrate scope with yields up to 95%, good functional group tolerance, and functionality of natural products. The 2-arylpyridine N-oxide

  过渡金属催化的 C-C 键活化已成为一种日益有效的分子骨架重组方法。酮作为一种多功能的功能分子，其 C-C 键活化反应已被广泛研究。然而，大多数无张力酮的C-C键活化通常遵循氧化加成策略，而羰基部分的亲核1,2-加成随后β-C消除策略的研究较少。这里描述了钯催化的无张力酮的 C-C 键活化，通过可去除的导向基团通过 β-C 消除来合成 2-芳基吡啶。该方案具有底物范围宽、收率高达95%、良好的官能团耐受性以及天然产物的功能等特点。2-芳基吡啶N-氧化物产物在温和的反应条件下可以很容易地转化为相应的2-芳基吡啶。
• 361. N-oxides and related compounds. Part XI. Mononitration of 2-, 3-, and 4-phenyl- and 2- and 4-benzyl-pyridine 1-oxide
  作者：A. R. Hands、A. R. Katritzky

  DOI：10.1039/jr9580001754

  日期：——
• Hisano, Takuzo; Matsuoka, Toshikazu; Fukunaga, Kazuhiro, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 10, p. 3776 - 3781
  作者：Hisano, Takuzo、Matsuoka, Toshikazu、Fukunaga, Kazuhiro、Ichikawa, Masataka

  DOI：——

  日期：——