(2-cyclohexenylpyrazolo[1,5-a]pyridin-5-yl)(phenyl)methanone | 1337985-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-cyclohexenylpyrazolo[1,5-a]pyridin-5-yl)(phenyl)methanone
• 英文别名: [2-(Cyclohexen-1-yl)pyrazolo[1,5-a]pyridin-5-yl]-phenylmethanone
• CAS: 1337985-04-2
• 化学式: C₂₀H₁₈N₂O
• 分子量: 302.376
• InChiKey: TVHDRCADONFNKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-苯甲酰吡啶 在 palladium bromide 、 三(4-甲氧苯基)膦 、 silver benzoate 、 碳酸氢钠 、 2,4-二硝基苯基羟胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 37.08h， 生成 (2-cyclohexenylpyrazolo[1,5-a]pyridin-5-yl)(phenyl)methanone
  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

• 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.