2-(E)-styryl-N-benzoyliminopyridinium ylide | 1206884-59-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(E)-styryl-N-benzoyliminopyridinium ylide
• 英文别名: (Z)-N-[2-[(E)-2-phenylethenyl]pyridin-1-ium-1-yl]benzenecarboximidate
• CAS: 1206884-59-4
• 化学式: C₂₀H₁₆N₂O
• 分子量: 300.36
• InChiKey: MOUWCNNGHQPRER-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 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：
  39.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(E)-styryl-N-benzoyliminopyridinium ylide 在 palladium bromide 、 三(4-甲氧苯基)膦 、 silver benzoate 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以56%的产率得到2-phenylpyrazolo[1,5-a]pyridine
  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
• 作为产物：
  描述：

  N-iminopyridinium ylide 在 potassium carbonate 、 sodium hydroxide 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 21.16h， 生成 2-(E)-styryl-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

• Copper-Catalyzed Direct Alkenylation of<i>N</i>-Iminopyridinium Ylides
  作者：James J. Mousseau、James A. Bull、André B. Charette

  DOI：10.1002/anie.200906020

  日期：2010.2.1

  A versatile Cu‐catalyzed direct CH alkenylation of N‐iminopyridinium ylides, compatible with several different copper sources (including a penny), provides a powerful and inexpensive method for the synthesis of functionalized pyridine derivatives. Chemoselective functionalization of halide‐containing compounds allows the synthesis of alkenyl pyridines containing reactive tethers for further functionalization

  一种多功能的Cu催化的直接Ç  H的烯基化Ñ -iminopyridinium叶立德，与几个不同的铜源（包括一个便士）兼容，提供了一种用于官能化的吡啶衍生物的合成一个强大的和廉价的方法。含卤化物的化学选择性官能化可以合成含反应性链的烯基吡啶，以进一步官能化。
• 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.