5-n-Pentyl-1,2,4-benzenetricarbonitrile | 140667-03-4

• 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-n-Pentyl-1,2,4-benzenetricarbonitrile
• 英文别名: 5-pentylbenzene-1,2,4-tricarbonitrile
• CAS: 140667-03-4
• 化学式: C₁₄H₁₃N₃
• 分子量: 223.277
• InChiKey: AEOXRFPHCDTOFX-UHFFFAOYSA-N

物化性质

• 沸点：
  398.5±42.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-甲基-2-戊基-1,3-二氧戊环 、 1,2,4,5-四氰基苯 以 乙腈 为溶剂， 生成 5-n-Pentyl-1,2,4-benzenetricarbonitrile
  参考文献：
  名称：

  Radicals through Photoinduced Electron Transfer. Addition to Olefin and Addition to Olefin-Aromatic Substitution Reactions

  摘要：

  The radical cations of 2,2-dialkyl- and 2-alkyl-2-aryl-1,3-dioxolanes, when generated in solution by photoinduced electron transfer to 1,2,4,5-benzenetetracarbonitrile (TCB), fragment to yield alkyl radicals. These are trapped by electron-withdrawing substituted alkenes (acrylonitrile, methyl acrylate, methyl vinyl ketone, as well as dimethyl maleate and fumarate). The radicals thus formed are either reduced by the TCB radical anion or add to it. In the first process (observed only with the diesters) the end result is reductive alkylation of the olefin, while the latter process results in an addition to the olefin-aromatic substitution reaction, The selectivity of the process is explained on the basis of steric hindrance, since the radicals react when still in the cage with the aromatic radical anion.

  DOI：

  10.1021/jo00098a019

文献信息

• 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。
• Mella, Mariella; d'Alessandro, Nicola; Freccero, Mauro, Journal of the Chemical Society. Perkin transactions II, 1993, # 3, p. 515 - 519
  作者：Mella, Mariella、d'Alessandro, Nicola、Freccero, Mauro、Albini, Angelo

  DOI：——

  日期：——
• Mella Mariella, Fagnoni Maurizio, Albini Angelo, J. Org. Chem, 59 (1994) N 19, S 5614-5622
  作者：Mella Mariella, Fagnoni Maurizio, Albini Angelo

  DOI：——

  日期：——
• Radicals through Photoinduced Electron Transfer. Addition to Olefin and Addition to Olefin-Aromatic Substitution Reactions
  作者：Mariella Mella、Maurizio Fagnoni、Angelo Albini

  DOI：10.1021/jo00098a019

  日期：1994.9

  The radical cations of 2,2-dialkyl- and 2-alkyl-2-aryl-1,3-dioxolanes, when generated in solution by photoinduced electron transfer to 1,2,4,5-benzenetetracarbonitrile (TCB), fragment to yield alkyl radicals. These are trapped by electron-withdrawing substituted alkenes (acrylonitrile, methyl acrylate, methyl vinyl ketone, as well as dimethyl maleate and fumarate). The radicals thus formed are either reduced by the TCB radical anion or add to it. In the first process (observed only with the diesters) the end result is reductive alkylation of the olefin, while the latter process results in an addition to the olefin-aromatic substitution reaction, The selectivity of the process is explained on the basis of steric hindrance, since the radicals react when still in the cage with the aromatic radical anion.