Fveongrajwnkin-uhfffaoysa- | 139071-44-6

• 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: Fveongrajwnkin-uhfffaoysa-
• 英文别名: methyl 6-(2,4,5-tricyanophenyl)hexanoate
• CAS: 139071-44-6
• 化学式: C₁₆H₁₅N₃O₂
• 分子量: 281.314
• InChiKey: FVEONGRAJWNKIN-UHFFFAOYSA-N

物化性质

• 沸点：
  466.8±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  97.7
• 氢给体数：
  0
• 氢受体数：
  5

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 生成 Fveongrajwnkin-uhfffaoysa- 、 Methyl 6-[2,4-dicyano-5-(6-methoxy-6-oxohexyl)phenyl]hexanoate 、 Methyl 6-[2,5-dicyano-4-(6-methoxy-6-oxohexyl)phenyl]hexanoate 、 Methyl 6-[4,5-dicyano-2-(6-methoxy-6-oxohexyl)phenyl]hexanoate
  参考文献：
  名称：

  Electron transfer photoinduced cleavage of acetals. A mild preparation of alkyl radicals

  摘要：

  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.

  DOI：

  10.1021/jo00037a020

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.

表征谱图