2-(4-chlorobenzyl)succinonitrile | 1392832-21-1

• 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-chlorobenzyl)succinonitrile
• 英文别名: 2-[(4-Chlorophenyl)methyl]butanedinitrile
• CAS: 1392832-21-1
• 化学式: C₁₁H₉ClN₂
• 分子量: 204.659
• InChiKey: YCNKRUCNZWDCRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4-氯苯基)甲基三甲基硅烷 、 反丁烯二腈 在 lithium perchlorate 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以93%的产率得到2-(4-chlorobenzyl)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

• Smooth Photocatalyzed Benzylation of Electrophilic Olefins via Decarboxylation of Arylacetic Acids
  作者：Luca Capaldo、Luca Buzzetti、Daniele Merli、Maurizio Fagnoni、Davide Ravelli

  DOI：10.1021/acs.joc.6b00984

  日期：2016.8.19

  Arylacetic acids were used as sources of benzyl radicals under tetrabutylammonium decatungstate photocatalyzed conditions for the benzylation of electron-poor olefins. The reaction proceeds smoothly in a mixed aqueous medium (MeCN/H2O 2/1) in the presence of NaHCO3, NaClO4, and an electron transfer agent (biphenyl). The reaction tolerates a wide variety of functional groups on the aromatic ring (whether

  在四丁基铵去癸酸盐光催化条件下，丙烯酸被用作苄基的来源，用于贫电子烯烃的苄基化。在NaHCO 3，NaClO 4和电子转移剂（联苯）的存在下，反应在混合水性介质（MeCN / H 2 O 2/1）中平稳进行。该反应可耐受芳环上的各种官能团（无论是供电子还是吸电子），并可扩展为杂芳族类似物。烯烃具有自由基陷阱和电子受体的双重作用。本方法还可扩展至芳基丙酸（包括非甾体抗炎药布洛芬和氟比洛芬），以及扁桃酸衍生物。
• 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