(E)-3-(3,5-二氯苯基)-3-(3,4-二甲氧基苯基)丙烯腈 | 1029095-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (E)-3-(3,5-二氯苯基)-3-(3,4-二甲氧基苯基)丙烯腈
• 英文名称: (E)-3-(3,5-dichlorophenyl)-3-(3,4-dimethoxyphenyl)acrylonitrile
• 英文别名: (E)-3-(3,5-dichlorophenyl)-3-(3,4-dimethoxyphenyl)prop-2-enenitrile
• CAS: 1029095-84-8
• 化学式: C₁₇H₁₃Cl₂NO₂
• 分子量: 334.202
• InChiKey: YUINTECUUPJOBF-PJQLUOCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(3,4-dimethoxyphenyl)propiolonitrile 、 3,5-二氯苯硼酸 在 copper (I) acetate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以97%的产率得到(E)-3-(3,5-二氯苯基)-3-(3,4-二甲氧基苯基)丙烯腈
  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

文献信息

• Stereoselective Synthesis of 3,3-Diarylacrylonitriles as Tubulin Polymerization Inhibitors
  作者：Zhenglai Fang、Yunlong Song、Taradas Sarkar、Ernest Hamel、William E. Fogler、Gregory E. Agoston、Phillip E. Fanwick、Mark Cushman

  DOI：10.1021/jo800428b

  日期：2008.6.1

  A series of 3,3-diarylacrylonitriles were synthesized stercoselectively as tubulin polymerization inhibitors for potential use in cancer chemotherapy. This synthetic route features stannylcupration and palladium-catalyzed Stille cross-coupling chemistry, allowing both E and Z isomers of 3,3-diarylacrylonitriles to be prepared in a very short sequence of reactions.
• Copper-Catalyzed Stereoselective Hydroarylation of 3-Aryl-2- propynenitriles with Arylboronic Acids
  作者：Yoshihiko Yamamoto、Tsuyoshi Asatani、Naohiro Kirai

  DOI：10.1002/adsc.200900067

  日期：2009.6

  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.