(Z)-3-bromo-4-(4-bromophenyl)-4-oxo-2-phenylbut-2-enenitrile | 1095272-40-4

• 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: (Z)-3-bromo-4-(4-bromophenyl)-4-oxo-2-phenylbut-2-enenitrile
• CAS: 1095272-40-4
• 化学式: C₁₆H₉Br₂NO
• 分子量: 391.062
• InChiKey: UIQFKAFJDWETGF-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3-bromo-4-(4-bromophenyl)-4-oxo-2-phenylbut-2-enenitrile 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以80%的产率得到(Z)-2-bromo-1-(4-bromophenyl)-3-cyano-3-phenylprop-2-en-1-ol
  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
• 作为产物：
  描述：

  三甲基氰硅烷 、 1-(4-溴苯基)-3-苯基丙炔酮 在 bis(1,5-cyclooctadiene)nickel (0) 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以84%的产率得到(Z)-3-bromo-4-(4-bromophenyl)-4-oxo-2-phenylbut-2-enenitrile
  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.