1-(2,4,5-tricyanophenyl)-1,2,3,4-tetrahydronaphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-(2,4,5-tricyanophenyl)-1,2,3,4-tetrahydronaphthalene
• 英文别名: 5-(1,2,3,4-Tetrahydronaphthalen-1-yl)benzene-1,2,4-tricarbonitrile；5-(1,2,3,4-tetrahydronaphthalen-1-yl)benzene-1,2,4-tricarbonitrile
• 化学式: C₁₉H₁₃N₃
• 分子量: 283.332
• InChiKey: YIWVZNHZFPUEEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  1,2,3,4-四氢萘 、 1,2,4,5-四氰基苯 以 乙腈 为溶剂， 反应 48.0h， 以74%的产率得到1-(2,4,5-tricyanophenyl)-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Photoreactions of 1,2,4,5-benzenetetracarbonitrile with arylethenes—photo- olefin dimerization–aromatic substitution reactions

  摘要：

  Irradiation of 1,2,4,5-tetracyanobenzene (TCNB) with styrene derivatives 1-4, respectively, leads to a photochemical olefin dimeiization-aromatic substitution reaction to give the corresponding (2,4,5-tricyanophenyl)tetralin derivative (8, 12, 16, 17, and 20) as the main product. Further irradiation of the primary product with alkene results in substitution of the meta-CN group by another phenyltetralinyl to give the corresponding 4:1 (alkene-TCNB) product. According to the effect of the codonor (biphenyl) and salt (magnesium perchlorate) on reaction rate, the result of photoinduced reactions of TCNB with tetralin (6) and 1-phenyltetralin (7) and analysis of the known kinetic data for relevant processes in the cyanoarene-alkene reactions, the mechanism for the formation of the olefin dimerization-aromatic substitution products (such as 8) is proposed to involve radical pair combination of the alkene cyclodimer radical (the corresponding 4-phenyl-1-tetralinyl radical) with TCNB-center dot followed by expulsion of a CN-. Photoreactions of TCNB with the alkene photocyclodimer (1-phenyltetralin) may also make minor contributions. Photoinduced reaction of TCNB with I -phenyleyclohexene (5) takes a different pathway from 1-4 to afford the 1: 1 (5-TCNB) primary product 21 by deprotonation of 5(+center dot) and radical pair combination with TCNB-center dot followed by elimination of HCN. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.089

文献信息

• Photoreactions of 1,2,4,5-benzenetetracarbonitrile with arylethenes—photo- olefin dimerization–aromatic substitution reactions
  作者：Min Zhang、Zhi-Feng Lu、Yun Liu、Günter Grampp、Hong-Wen Hu、Jian-Hua Xu

  DOI：10.1016/j.tet.2006.03.089

  日期：2006.6

  Irradiation of 1,2,4,5-tetracyanobenzene (TCNB) with styrene derivatives 1-4, respectively, leads to a photochemical olefin dimeiization-aromatic substitution reaction to give the corresponding (2,4,5-tricyanophenyl)tetralin derivative (8, 12, 16, 17, and 20) as the main product. Further irradiation of the primary product with alkene results in substitution of the meta-CN group by another phenyltetralinyl to give the corresponding 4:1 (alkene-TCNB) product. According to the effect of the codonor (biphenyl) and salt (magnesium perchlorate) on reaction rate, the result of photoinduced reactions of TCNB with tetralin (6) and 1-phenyltetralin (7) and analysis of the known kinetic data for relevant processes in the cyanoarene-alkene reactions, the mechanism for the formation of the olefin dimerization-aromatic substitution products (such as 8) is proposed to involve radical pair combination of the alkene cyclodimer radical (the corresponding 4-phenyl-1-tetralinyl radical) with TCNB-center dot followed by expulsion of a CN-. Photoreactions of TCNB with the alkene photocyclodimer (1-phenyltetralin) may also make minor contributions. Photoinduced reaction of TCNB with I -phenyleyclohexene (5) takes a different pathway from 1-4 to afford the 1: 1 (5-TCNB) primary product 21 by deprotonation of 5(+center dot) and radical pair combination with TCNB-center dot followed by elimination of HCN. (c) 2006 Elsevier Ltd. All rights reserved.