2-(2-fluorobenzoyl)-4-(2-fluorophenyl)-4-oxobutanenitrile | 1398565-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-fluorobenzoyl)-4-(2-fluorophenyl)-4-oxobutanenitrile
• CAS: 1398565-81-5
• 化学式: C₁₇H₁₁F₂NO₂
• 分子量: 299.277
• InChiKey: ORVWNUDZGDCKPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.93
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  苯丙炔醛 、 2-(2-fluorobenzoyl)-4-(2-fluorophenyl)-4-oxobutanenitrile 在 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 sodium benzoate 作用下， 以 苯 为溶剂， 反应 14.0h， 以50%的产率得到
  参考文献：
  名称：

  N-Heterocyclic Carbene-Catalyzed Annulation of α-Cyano-1,4-diketones with Ynals

  摘要：

  In this paper, the first stereoselective annulation reaction between alpha-cyano-1,4-diketones and ynals, mediated by catalytic amounts of a triazolium salt precatalyst and cocatalytic amounts of a weak carboxylate base, is disclosed. The title transformation proceeds smoothly under mild reaction conditions and generates three contiguous stereogenic centers, one of which is a quaternary acetal carbon. This reaction tolerates a wide variety of electronically distinct substituents on both reaction partners and affords privileged bicyclic scaffolds in 61-90% isolated yields and with up to 20:1 diastereomeric preference.

  DOI：

  10.1021/ol3022287
• 作为产物：
  描述：

  1,2-双(2-氟苯基)乙烷-1,2-二酮 、 丙烯腈 在 三甲基氰硅烷 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以37%的产率得到2-(2-fluorobenzoyl)-4-(2-fluorophenyl)-4-oxobutanenitrile
  参考文献：
  名称：

  N-Heterocyclic Carbene-Catalyzed Annulation of α-Cyano-1,4-diketones with Ynals

  摘要：

  In this paper, the first stereoselective annulation reaction between alpha-cyano-1,4-diketones and ynals, mediated by catalytic amounts of a triazolium salt precatalyst and cocatalytic amounts of a weak carboxylate base, is disclosed. The title transformation proceeds smoothly under mild reaction conditions and generates three contiguous stereogenic centers, one of which is a quaternary acetal carbon. This reaction tolerates a wide variety of electronically distinct substituents on both reaction partners and affords privileged bicyclic scaffolds in 61-90% isolated yields and with up to 20:1 diastereomeric preference.

  DOI：

  10.1021/ol3022287