(benzoyl)(2,6-dimethylpyridin-1-ium-1-yl)amide

• 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: (benzoyl)(2,6-dimethylpyridin-1-ium-1-yl)amide
• 英文别名: 2,6-dimethyl-N-benzoyliminopyridinium ylide；N-Benzoylimino-2,6-dimethyl-pyridiniumbetain；(Z)-N-(2,6-dimethylpyridin-1-ium-1-yl)benzenecarboximidate
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: CQFBHPUXCVCVRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (benzoyl)(2,6-dimethylpyridin-1-ium-1-yl)amide 、 甲基溴化镁 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 以31 mg的产率得到N-(2,6,6-trimethyl-3,6-dihydropyridin-1(2H)-yl)benzamide
  参考文献：
  名称：

  Complexation Promoted Additions to N-Benzoyliminopyridinium Ylides. A Novel and Highly Regioselective Approach to Polysubstituted Piperidines

  摘要：

  Unprecedented regioselectivities were observed for the addition of different organometallic nucleophiles to N-benzoyliminopyridinium ylides. Even benzylic and branched aliphatic Grignard reagents, which usually give substantial amounts of 1,4-adducts, showed excellent 1,2-regioselectivities. The electronic nature of the pyridinium ylide is taken into account to explain these results.

  DOI：

  10.1021/ja0348647
• 作为产物：
  描述：

  2,6-二甲基吡啶 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 生成 (benzoyl)(2,6-dimethylpyridin-1-ium-1-yl)amide
  参考文献：
  名称：

  通过不对称内部炔烃的分子间[3 + 2]-环加成反应实现2,4,5-（杂）芳基取代的恶唑的高度区域选择性合成。

  摘要：

  稳健的N-亲核1,3-N，O-偶极当量在金催化下与不对称内部炔烃反应。来自遥远的氮孤对的缀合使能并控制该会聚且高度区域选择性的过程。

  DOI：

  10.1039/c3cc45410j

文献信息

• Highly Efficient Synthesis of <i>O</i>-(2,4-Dinitrophenyl)hydroxylamine. Application to the Synthesis of Substituted <i>N</i>-Benzoyliminopyridinium Ylides
  作者：Claude Legault、André B. Charette

  DOI：10.1021/jo034456l

  日期：2003.9.1

  efficient two-step synthesis of O-(2,4-dinitrophenyl)hydroxylamine is described along with a comparison of its aminating efficiency with O-mesitylenesulfonylhydroxylamine (MSH). It was used in an expedient N-amination/benzoylation procedure involving various substituted pyridines, leading to polysubstituted N-benzoyliminopyridinium ylides, and the scope of its amination power was studied.

  描述了一种有效的两步合成O-（2,4-二硝基苯基）羟胺的方法，并比较了其与O-次甲基亚磺酰基羟胺（MSH）的胺化效率。它被用于方便的N-氨基化/苯甲酰化过程，涉及各种取代的吡啶，导致多取代的N-苯并亚氨基吡啶基吡啶化，并研究了其胺化能力的范围。
• Dearomatization of Pyridines: Photochemical Skeletal Enlargement for the Synthesis of 1,2-Diazepines
  作者：Elise Boudry、Flavien Bourdreux、Jérôme Marrot、Xavier Moreau、Clément Ghiazza

  DOI：10.1021/jacs.3c14467

  日期：2024.1.31

  derivatives, affording unique 7-membered structures. Mechanistic evidence supports the transient presence of a diazanorcaradiene species. Finally, pertinent transformations of the products, including ring contraction reactions to form pyrazoles, were conducted and paved the way to a broad application of the developed protocol.

  在本报告中，我们开发了一种统一且标准化的一锅序列，通过插入氮原子将吡啶衍生物转化为1,2-二氮杂卓。这种骨架转变利用了 1-氨基吡啶鎓叶立德的原位生成，该叶立德在紫外线照射下会重新排列。对关键参数（波长、反应条件、活化剂）的彻底评估使我们能够制定出简单、温和且用户友好的方案。该模型反应被外推到 40 多个实例，包括药物衍生物，提供了独特的 7 元结构。机理证据支持二氮正环烯类物质的短暂存在。最后，对产品进行了相关转化，包括环收缩反应形成吡唑，并为所开发方案的广泛应用铺平了道路。
• Complexation Promoted Additions to <i>N</i>-Benzoyliminopyridinium Ylides. A Novel and Highly Regioselective Approach to Polysubstituted Piperidines
  作者：Claude Legault、André B. Charette

  DOI：10.1021/ja0348647

  日期：2003.5.1

  Unprecedented regioselectivities were observed for the addition of different organometallic nucleophiles to N-benzoyliminopyridinium ylides. Even benzylic and branched aliphatic Grignard reagents, which usually give substantial amounts of 1,4-adducts, showed excellent 1,2-regioselectivities. The electronic nature of the pyridinium ylide is taken into account to explain these results.
• Highly regioselective synthesis of 2,4,5-(hetero)aryl substituted oxazoles by intermolecular [3+2]-cycloaddition of unsymmetrical internal alkynes
  作者：Elli Chatzopoulou、Paul W. Davies

  DOI：10.1039/c3cc45410j

  日期：——

  A robust N-nucleophilic 1,3-N,O-dipole equivalent reacts with unsymmetrical internal alkynes under gold catalysis. Conjugation from a remote nitrogen lone pair enables and controls this convergent and highly regioselective process.

  稳健的N-亲核1,3-N，O-偶极当量在金催化下与不对称内部炔烃反应。来自遥远的氮孤对的缀合使能并控制该会聚且高度区域选择性的过程。