(E)-5-(1-methyl-2-pentenyl)benzene-1,2,4-tricarbonitrile

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-5-(1-methyl-2-pentenyl)benzene-1,2,4-tricarbonitrile
• 英文别名: 5-[(E)-hex-3-en-2-yl]benzene-1,2,4-tricarbonitrile
• 化学式: C₁₅H₁₃N₃
• 分子量: 235.288
• InChiKey: OKDOCWPTGBHYIH-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  反-2-已烯 、 1,2,4,5-四氰基苯 以 乙腈 为溶剂， 反应 13.0h， 以3.5%的产率得到(E)-5-(1-methyl-2-pentenyl)benzene-1,2,4-tricarbonitrile
  参考文献：
  名称：

  2 + 2 + 2 Cycloaddition vs Radical Ion Chemistry in the Photoreactions of 1,2,4,5-Benzenetetracarbonitrile with Alkenes in Acetonitrile

  摘要：

  Irradiation of 1,2,4,5-benzenetetracarbonitrile (TCB) in acetonitrile in the presence of 1-hexene leads to two isomeric tetrahydroisoquinolines through a 2 + 2 + 2 cycloaddition between TCB, the alkene, and MeCN. The process occurs with moderate quantum yield via a strongly polarized exciplex. With di- and polysubstituted alkenes no cycloaddition takes place, the only reaction observed being substitution of a cyano group by an allyl radical. This is a low quantum yield process occurring via deprotonation of the alkene radical cation and TCB*(-)-allyl radical coupling. The selectivity in the attack on the allyl radical depends on steric hindering. Alternatively, the alkene radical cation can be trapped by methanol, yielding a (beta-methoxyethyl)benzenetricarbonitrile. In the presence of water, the corresponding alcohols are not isolated, since they rapidly fragment to yield alkylbenzenetricarbonitriles. The mechanism is discussed on the basis of the competition of chemical reactions and back electron transfer.

  DOI：

  10.1021/ja00101a027