(E)-3-(4-fluorophenyl)-3-(4-hydroxyphenyl)acrylonitrile

• 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: (E)-3-(4-fluorophenyl)-3-(4-hydroxyphenyl)acrylonitrile
• 英文别名: (E)-3-(4-fluorophenyl)-3-(4-hydroxyphenyl)prop-2-enenitrile
• 化学式: C₁₅H₁₀FNO
• 分子量: 239.249
• InChiKey: ATWAJCHCGIUSER-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基苯硼酸 、 (Z)-3-chloro-3-(4-fluorophenyl)-2-propenenitrile 在 potassium fluoride 、 tris(dibenzylideneacetone)dipalladium (0) 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以89%的产率得到(E)-3-(4-fluorophenyl)-3-(4-hydroxyphenyl)acrylonitrile
  参考文献：
  名称：

  Synthesis of the Benzhydryl Motif via a Suzuki−Miyaura Coupling of Arylboronic Acids and 3-Chloroacrylonitriles

  摘要：

  A simple two-step procedure for synthesizing functionalized benzhydrylamines is described. The first step involves a Suzuki-Miyaura coupling reaction between arylboronic acids and 3-chloro-3-arylacrylonitriles at 45 degrees C. A variety of boronic acids and substituted acrylonitriles can be used for the reaction. The resulting 3,3-diaryl-substituted acrylonitriles can be converted into their corresponding Boc-protected amines by catalytic hydrogenation.

  DOI：

  10.1021/jo0519615

文献信息

• Synthesis of the Benzhydryl Motif via a Suzuki−Miyaura Coupling of Arylboronic Acids and 3-Chloroacrylonitriles
  作者：Steven J. Taylor、Matthew R. Netherton

  DOI：10.1021/jo0519615

  日期：2006.1.1

  A simple two-step procedure for synthesizing functionalized benzhydrylamines is described. The first step involves a Suzuki-Miyaura coupling reaction between arylboronic acids and 3-chloro-3-arylacrylonitriles at 45 degrees C. A variety of boronic acids and substituted acrylonitriles can be used for the reaction. The resulting 3,3-diaryl-substituted acrylonitriles can be converted into their corresponding Boc-protected amines by catalytic hydrogenation.