4-(1-Adamantyl)-4-oxobutanenitrile | 135074-04-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(1-Adamantyl)-4-oxobutanenitrile
• CAS: 135074-04-3
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: SRVBHXSNTMTXLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  一氧化碳 、 1-吲哚金刚烷 、 丙烯腈 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 80.0 ℃ 、8.11 MPa 条件下， 反应 3.0h， 以46%的产率得到4-(1-Adamantyl)-4-oxobutanenitrile
  参考文献：
  名称：

  Double alkylation of carbon monoxide via free radicals: synthesis of unsymmetrical ketones

  摘要：

  A novel method for the synthesis of unsymmetrical ketones via the free radical carbonylation of alkyl halides is described. The mechanism of the reaction involves the trapping of an alkyl free radical by CO, the addition of the acyl free radical so formed to an alkene, and termination of the reaction by the abstraction of a hydrogen atom from tributyltin hydride by the product acyl-substituted free radical.

  DOI：

  10.1021/jo00017a001

文献信息

• Double alkylation of carbon monoxide via free radicals: synthesis of unsymmetrical ketones
  作者：Ilhyong Ryu、Kazuya Kusano、Hiroshi Yamazaki、Noboru Sonoda

  DOI：10.1021/jo00017a001

  日期：1991.8

  A novel method for the synthesis of unsymmetrical ketones via the free radical carbonylation of alkyl halides is described. The mechanism of the reaction involves the trapping of an alkyl free radical by CO, the addition of the acyl free radical so formed to an alkene, and termination of the reaction by the abstraction of a hydrogen atom from tributyltin hydride by the product acyl-substituted free radical.