4-benzoyl-N-benzoyliminopyridinium ylide | 188482-71-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-benzoyl-N-benzoyliminopyridinium ylide
• 英文别名: N-(4-benzoylpyridin-1-ium-1-yl)benzenecarboximidate
• CAS: 188482-71-5
• 化学式: C₁₉H₁₄N₂O₂
• 分子量: 302.332
• InChiKey: LKYPIAFHOXLSBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzoyl-N-benzoyliminopyridinium ylide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以55%的产率得到N-[4-(Hydroxy-phenyl-methyl)-3,6-dihydro-2H-pyridin-1-yl]-benzamide
  参考文献：
  名称：

  Okoro, Cosmas O.; Wilson, Tiffany L.; Choi, JongOh, Medicinal Chemistry Research, 1997, vol. 7, # 1, p. 1 - 15

  摘要：

  DOI：
• 作为产物：
  描述：

  4-苯甲酰吡啶 在 碳酸氢钠 、 2,4-二硝基苯基羟胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 21.08h， 生成 4-benzoyl-N-benzoyliminopyridinium ylide
  参考文献：
  名称：

  Synthesis of 2- and 2,3-Substituted Pyrazolo[1,5-a]pyridines: Scope and Mechanistic Considerations of a Domino Direct Alkynylation and Cyclization of N-Iminopyridinium Ylides Using Alkenyl Bromides, Alkenyl Iodides, and Alkynes

  摘要：

  Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a]pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.

  DOI：

  10.1021/jo201303x

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。
• Synthesis of 2- and 2,3-Substituted Pyrazolo[1,5-<i>a</i>]pyridines: Scope and Mechanistic Considerations of a Domino Direct Alkynylation and Cyclization of <i>N</i>-Iminopyridinium Ylides Using Alkenyl Bromides, Alkenyl Iodides, and Alkynes
  作者：James J. Mousseau、James A. Bull、Carolyn L. Ladd、Angélique Fortier、Daniela Sustac Roman、André B. Charette

  DOI：10.1021/jo201303x

  日期：2011.10.21

  Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a]pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.
• Okoro, Cosmas O.; Wilson, Tiffany L.; Choi, JongOh, Medicinal Chemistry Research, 1997, vol. 7, # 1, p. 1 - 15
  作者：Okoro, Cosmas O.、Wilson, Tiffany L.、Choi, JongOh、Redda, Kinfe K.

  DOI：——

  日期：——