2-(4-cyanobenzyl)succinonitrile | 1392832-24-4

• 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: 2-(4-cyanobenzyl)succinonitrile
• 英文别名: 2-[(4-Cyanophenyl)methyl]butanedinitrile
• CAS: 1392832-24-4
• 化学式: C₁₂H₉N₃
• 分子量: 195.224
• InChiKey: HEVFWYJDPMYHFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-((trimethylsilyl)methyl)benzonitrile 、 反丁烯二腈 在 lithium perchlorate 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以43%的产率得到2-(4-cyanobenzyl)succinonitrile
  参考文献：
  名称：

  Decatungstate As Photoredox Catalyst: Benzylation of Electron-Poor Olefins

  摘要：

  Excited tetrabutylammonium decatungstate (TBADT), known to activate a variety of compounds via hydrogen atom transfer (HAT), has now been applied as a photoredox catalyst for the effective oxidative cleavage of benzyl silanes and radical benzylation of reducible olefins occurring in isolated yields from poor to excellent.

  DOI：

  10.1021/ol301900p

文献信息

• Decatungstate Photocatalyzed Benzylation of Alkenes with Alkylaromatics
  作者：Hisham Qrareya、Davide Ravelli、Maurizio Fagnoni、Angelo Albini

  DOI：10.1002/adsc.201300598

  日期：2013.10.11

  AbstractThe direct benzylation of electrophilic alkenes with alkylbenzenes has been achieved by decatungstate photocatalysis in a high ionic strength medium (5:1 acetonitrile/water mixed solvents, 0.5 M lithium perchlorate). The reaction has been extended to ring‐substituted (Cl, F, CN) toluenes and further alkylbenzenes. Intramolecular selectivity (p‐cymene, 4‐methylanisole) and deuteration effects support the atom transfer character of the process that, however, requires a sufficient stabilization of the intermediate polar exciplex to occur. The reactivity of the decatungstate anion is compared with that of aromatic ketones, the benchmark of photochemical hydrogen/electron transfer processes.magnified image