ethyl 3-cyano-3-methyl-5-hexenoate | 1199790-81-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-cyano-3-methyl-5-hexenoate
• 英文别名: Ethyl 3-cyano-3-methylhex-5-enoate
• CAS: 1199790-81-2
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: ZXARPGMRFSFREC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  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， 以74%的产率得到ethyl 3-cyano-3-methyl-5-hexenoate
  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