(+/-)-2-methyl-2-phenyl-4-hexenenitrile | 1199790-86-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+/-)-2-methyl-2-phenyl-4-hexenenitrile
• 英文别名: 2-methyl-2-phenyl-4-hexenenitrile；2-Methyl-2-phenylhex-4-enenitrile
• CAS: 1199790-86-7
• 化学式: C₁₃H₁₅N
• 分子量: 185.269
• InChiKey: MWKPIQORHFNFRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  but-2-en-1-yl 2-cyano-2-phenylpropanoate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 生成 (+/-)-2-methyl-2-phenyl-4-hexenenitrile 、 2,3-dimethyl-2-phenylpent-4-enenitrile
  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

• Transition metal-free addition of ketones or nitriles to 1,3-dienes
  作者：Jean-Marc Gaudin、Pascal Millet

  DOI：10.1039/b715262k

  日期：——

  The simpler the better (or going green): The first examples of the catalytic addition of 1,3-dienes to simple ketones or nitriles are described. These reactions can be effected on a kilogram scale, representing the shortest access featuring a perfect atom economy to molecules of interest in the perfume industry.

  简而美之（或绿色化）：首次报道了1,3-二烯与简单酮或腈的催化加成反应实例。这些反应可在千克级规模上实现，代表了以完美的原子经济性获取香水行业中感兴趣分子的最短途径。