2-(cyclohex-2-enyl)-2-phenylpropanenitrile | 107427-29-2

• 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-(cyclohex-2-enyl)-2-phenylpropanenitrile
• 英文别名: 2-Cyclohex-2-en-1-yl-2-phenylpropanenitrile；2-cyclohex-2-en-1-yl-2-phenylpropanenitrile
• CAS: 107427-29-2
• 化学式: C₁₅H₁₇N
• 分子量: 211.307
• InChiKey: OMUKIJJVDMUYCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  cyclohex-2-en-1-yl 2-cyano-2-phenylpropanoate 在 四(三苯基膦)钯 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 以75%的产率得到2-(cyclohex-2-enyl)-2-phenylpropanenitrile
  参考文献：
  名称：

  Regiospecific Decarboxylative Allylation of Nitriles

  摘要：

  Palladium-catalyzed decarboxylative alpha-allylation of nitriles readily occurs with use of Pd-2(dba)(3) and rac-BINAP. This catalyst mixture also allows the highly regiospecific alpha-allylation of nitrites in the presence of much more acidic (x-protons. Thus, the reported method provides access to compounds that are not readily available via base-mediated allylation chemistries. Lastly, mechanistic investigations indicate that there is a competition between C- and N-allylation of an intermediate nitrile-stabilized anion and that N-allylation is followed by a rapid [3,3]-sigmatropic rearrangement.

  DOI：

  10.1021/ol902065p

文献信息

• Lebedev, S. A.; Starosel'skaya, L. F.; Petrov, E. S., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 7, p. 1410
  作者：Lebedev, S. A.、Starosel'skaya, L. F.、Petrov, E. S.

  DOI：——

  日期：——
• Regiospecific Decarboxylative Allylation of Nitriles
  作者：Antonio Recio、Jon A. Tunge

  DOI：10.1021/ol902065p

  日期：2009.12.17

  Palladium-catalyzed decarboxylative alpha-allylation of nitriles readily occurs with use of Pd-2(dba)(3) and rac-BINAP. This catalyst mixture also allows the highly regiospecific alpha-allylation of nitrites in the presence of much more acidic (x-protons. Thus, the reported method provides access to compounds that are not readily available via base-mediated allylation chemistries. Lastly, mechanistic investigations indicate that there is a competition between C- and N-allylation of an intermediate nitrile-stabilized anion and that N-allylation is followed by a rapid [3,3]-sigmatropic rearrangement.