苯己酸,2,4,5-三氰基-,2-羟基乙基酯 | 139071-41-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯己酸,2,4,5-三氰基-,2-羟基乙基酯
• 英文名称: 2-Hydroxyethyl 6-(2,4,5-tricyanophenyl)hexanoate
• CAS: 139071-41-3
• 化学式: C₁₇H₁₇N₃O₃
• 分子量: 311.34
• InChiKey: CBWIOZKTLBDKRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,4-二氧螺环[4,5]癸烷 、 1,2,4,5-四氰基苯 以69%的产率得到
  参考文献：
  名称：

  Mella Mariella, Freccero Mauro, Albini Angelo, J. Org. Chem, 59 (1994) N 5, S 1047-1052

  摘要：

  DOI：

文献信息

• Electron transfer photoinduced cleavage of acetals. A mild preparation of alkyl radicals
  作者：M. Mella、E. Fasani、A. Albini

  DOI：10.1021/jo00037a020

  日期：1992.5

  Electron transfer from 2-alkyl- and 2,2-dialkyldioxolanes as well as from open-chain ketals to singlet excited benzene-1,2,4,5-tetracarbonitrile (TCNB) is followed by fragmentation of the donors radical cation to yield alkyl radicals and dialkoxy carbocations. The first species are trapped by TCNB to yield alkylbenzenetricarbonitriles (substitution of a second cyano group can be obtained sequentially) and in a minor path are reduced to alkanes, while the latter ones react with nucleophiles to give ortho acid derivatives. In view of the results of radical clock experiments, it is assumed that part of the process is a concerted (radical cation cleavage-addition to the aromatic) reaction, while another part involves the free-radical cation. On the other hand, intersystem crossing from the singlet radical ion pair to the triplet manifold causes cleavage of the acetal to the corresponding carbonyl derivative. This reaction offers a mild method for the preparation of alkyl radicals via C-C bond cleavage.
• 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.