(E)-2-(4-methoxyphenyl)-4-oxo-4-phenylbut-2-enenitrile | 1095272-32-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-2-(4-methoxyphenyl)-4-oxo-4-phenylbut-2-enenitrile
• CAS: 1095272-32-4
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: SNARGKAUIANDFP-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基氰硅烷 、 3-(4-甲氧基苯基)-1-苯丙酮 在 bis(1,5-cyclooctadiene)nickel (0) 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (E)-2-(4-methoxyphenyl)-4-oxo-4-phenylbut-2-enenitrile 、 (Z)-3-cyano-3-(4-methoxyphenyl)-1-phenyl-2-propen-1-one
  参考文献：
  名称：

  Ni(0)-Catalyzed Conjugate Addition of Me₃SiCN to Ynones: α-Bromo-β-cyano Tetrasubstituted Enones

  摘要：

  Conjugate addition of Me3SiCN to ynones is smoothly catalyzed by Ni(cod)(2) to give the beta-cyanosilyloxyallene quantitatively. Further reaction of the silyloxyallenes with NBS provides the tetrasubstituted alpha-bromo-beta-cyano enones in high yields (up to 95%) with excellent Z-selectivity (E/Z = up to >1/99). X-ray crystallographic analysis showed a bent structure of the alpha-bromo-beta-cyano enone due to a deconjugation of the pi-bond and carbonyl group.

  DOI：

  10.1021/ol802508q

文献信息

• Ni(0)-Catalyzed Conjugate Addition of Me₃SiCN to Ynones: α-Bromo-β-cyano Tetrasubstituted Enones
  作者：Takayoshi Arai、Yuuki Suemitsu、Yui Ikematsu

  DOI：10.1021/ol802508q

  日期：2009.1.15

  Conjugate addition of Me3SiCN to ynones is smoothly catalyzed by Ni(cod)(2) to give the beta-cyanosilyloxyallene quantitatively. Further reaction of the silyloxyallenes with NBS provides the tetrasubstituted alpha-bromo-beta-cyano enones in high yields (up to 95%) with excellent Z-selectivity (E/Z = up to >1/99). X-ray crystallographic analysis showed a bent structure of the alpha-bromo-beta-cyano enone due to a deconjugation of the pi-bond and carbonyl group.