5-butylbenzene-1,2,4-tricarbonitrile | 132381-81-8

• 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: 5-butylbenzene-1,2,4-tricarbonitrile
• 英文别名: 5-butyl-1,2,4-tricyanobenzene；5-Butyl-1,2,4-benzenetricarbonitrile
• CAS: 132381-81-8
• 化学式: C₁₃H₁₁N₃
• 分子量: 209.25
• InChiKey: XTFSVJCINVEZDM-UHFFFAOYSA-N

物化性质

• 沸点：
  387.1±42.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  dibutyldimethylsilane 、 1,2,4,5-四氰基苯 以 乙腈 为溶剂， 以72%的产率得到5-butylbenzene-1,2,4-tricarbonitrile
  参考文献：
  名称：

  通过光诱导的14族金属-碳σ供体的电子转移实现芳族腈的新型烷基化

  摘要：

  四烷基硅烷，-锗烷和-锡烷与芳族腈的光诱导电子转移反应可得到烷基化产物。通过使用基本时钟来研究该机制。

  DOI：

  10.1016/s0040-4039(00)97074-6

文献信息

• Cleavage of Tin-Carbon Bonds of Organosilylstannane and Organodistannane in Photo-Induced Electron Transfer Reactions and Mass Spectrometry
  作者：Soichiro Kyushin、Shinju Otani、Yasuhiro Nakadaira、Mamoru Ohashi

  DOI：10.1246/cl.1995.29

  日期：1995.1

  Photoalkylation of tetracyanobenzene and benzil with (n-Bu)3SnSiMe3 or (n-Bu)3SnSn(n-Bu)3 proceeds via electron transfer. In these reactions, the Sn–C bond of (n-Bu)3SnSiMe3 and (n-Bu)3SnSn(n-Bu)3 is cleaved in preference to the Sn–Si and Sn–Sn bonds. Similar cleavage of the Sn–C bond is also observed in mass spectra of these group 14 organometallic compounds.

  四氰基苯和苯偶酰与（n-Bu）3SnSiMe3或（n-Bu）3SnSn（n-Bu）3的照相烷基化是通过电子转移进行的。在这些反应中，（n-Bu）3SnSiMe3和（n-Bu）3SnSn（n-Bu）3的Sn-C键断裂优先于Sn-Si和Sn-Sn键。在14族有机金属化合物的质谱中，也观察到了类似的Sn-C键断裂。
• 2 + 2 + 2 Cycloaddition vs Radical Ion Chemistry in the Photoreactions of 1,2,4,5-Benzenetetracarbonitrile with Alkenes in Acetonitrile
  作者：Matteo Vanossi、Mariella Mella、Angelo Albini

  DOI：10.1021/ja00101a027

  日期：1994.11

  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.
• Kyushin Soichiro, Otani Shinju, Nakadaira Yasuhiro, Ohashi Mamoru, Chem. Lett, (1995) N 1, S 29-30
  作者：Kyushin Soichiro, Otani Shinju, Nakadaira Yasuhiro, Ohashi Mamoru

  DOI：——

  日期：——