5-ethylbenzene-1,2,4-tricarbonitrile | 140667-02-3

• 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-ethylbenzene-1,2,4-tricarbonitrile
• 英文别名: 5-Ethyl-1,2,4-tricyanobenzene
• CAS: 140667-02-3
• 化学式: C₁₁H₇N₃
• 分子量: 181.197
• InChiKey: VGPVAQBEFDXKDN-UHFFFAOYSA-N

物化性质

• 沸点：
  366.4±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  1,2,4,5-四氰基苯 、 丙酸 以 乙腈 为溶剂， 反应 2.0h， 以22%的产率得到5-ethylbenzene-1,2,4-tricarbonitrile
  参考文献：
  名称：

  Electron-donating behaviour of aliphatic carboxylic acids in the photoreaction with 1,2,4,5-tetracyanobenzene

  摘要：

  用脂肪族羧酸辐照 1,2,4,5-四氰基苯的乙腈溶液，可以高效地生成 2,4,5-三氰基烷基苯；电子从羧酸转移到激发的四氰基苯是必不可少的。

  DOI：

  10.1039/c39920000366

文献信息

• Alkyl radicals from t-butyl esters through photoinduced electron transfer
  作者：Elisa Fasani、Diego Peverali、Angelo Albini

  DOI：10.1016/0040-4039(94)88486-2

  日期：1994.12

  Alkyl radicals are obtained under mild conditions from 1,2,4,5-benzenetetracarbonitrile SET photosensitized fragmentation of t-butyl esters. The same process occurs with undissociated carboxylic acids.

  烷基是在温和条件下从叔丁基酯的1,2,4,5-苯四甲腈SET光敏片段获得的。未离解的羧酸也会发生相同的过程。
• Photochemical reaction of benzene-1,2,4,5-tetracarbonitrile with the ketals of cyclic and bicyclic ketones
  作者：Mariella Mella、Mauro Freccero、Angelo Albini

  DOI：10.1021/jo00084a021

  日期：1994.3

  The radical cations of the ethylene ketals of some cyclic and bicyclic ketones are generated by single electron transfer to excited benzene-1,2,4,5-tetracarbonitrile (TCB). Their fragmentation yields 1,5- and 1,6-distonic radical cations, which add to TCB-. to give [omega-[(2-hydroxyethoxy)carbonyl] alkyl]benzenetricarbonitriles. The reduction of the radical center occurs only to a small extent, and is enhanced in the presence of dodecylmercaptan, in the case of hindered radicals. The reaction of the camphor ethylene ketal (both alkylation of TCB and reduction) occurs with total diastereoselectivity at the reacting radical center.
• 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.
• Mella Mariella, Freccero Mauro, Albini Angelo, J. Org. Chem, 59 (1994) N 5, S 1047-1052
  作者：Mella Mariella, Freccero Mauro, Albini Angelo

  DOI：——

  日期：——
• Electron-donating behaviour of aliphatic carboxylic acids in the photoreaction with 1,2,4,5-tetracyanobenzene
  作者：Kazuo Tsujimoto、Nobuhisa Nakao、Mamoru Ohashi

  DOI：10.1039/c39920000366

  日期：——

  Irradiation of an acetonitrile solution of 1,2,4,5-tetracyanobenzene with aliphatic carboxylic acids gives 2,4,5-tricyanoalkylbenzenes efficiently; electron transfer from the carboxylic acids to the excited tetracyanobenzene is essential.

  用脂肪族羧酸辐照 1,2,4,5-四氰基苯的乙腈溶液，可以高效地生成 2,4,5-三氰基烷基苯；电子从羧酸转移到激发的四氰基苯是必不可少的。