(E)-3-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)acrylonitrile | 1198105-49-5

• 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-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)acrylonitrile
• CAS: 1198105-49-5
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: SMBNBGFQTGGSHP-CXUHLZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  60.71
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-(4-methoxyphenyl)propiolonitrile 、 3,4,5-三甲氧基苯硼酸 在 copper (I) acetate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以72%的产率得到(E)-3-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)acrylonitrile
  参考文献：
  名称：

  铜催化3-芳基-2-丙腈与芳基硼酸的立体选择性加氢芳基化

  摘要：

  Abstractmagnified imageThe selective synthesis of 3,3‐diarylacrylonitriles has been achieved by copper‐catalyzed hydroarylation of 3‐aryl‐2‐propynenitriles with arylboronic acids. The starting cyanoalkynes were efficiently prepared from the appropriate aromatic aldehydes and diethyl cyanomethylphosphonate in two steps. The hydroarylation of the obtained cyanoalkyne substrates proceeded in methanol at ambient temperature to produce 3,3‐diarylacrylonitriles in good to high yields with excellent syn selectivity. The present method was successfully applied to the regiospecific synthesis of both stereoisomers of CC‐5079, which was recently reported as a potent anticancer drug.

  DOI：

  10.1002/adsc.200900067