Allyl-((E)-but-1-enyl)-isobutyl-amine | 135535-86-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Allyl-((E)-but-1-enyl)-isobutyl-amine
• 英文别名: (E)-N-(2-methylpropyl)-N-prop-2-enylbut-1-en-1-amine
• CAS: 135535-86-3
• 化学式: C₁₁H₂₁N
• 分子量: 167.294
• InChiKey: ZMZQWIJCEGFAAR-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-Allyl-N-((E)-but-1-enyl)-isobutyramide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以95%的产率得到Allyl-((E)-but-1-enyl)-isobutyl-amine
  参考文献：
  名称：

  Preparation of 3-aza-Cope rearrangement of N-alkyl-N-allyl enamines

  摘要：

  The [3,3] charge-accelerated rearrangement of N-allyl-N-isobutyl enamine substrates to gamma,delta-unsaturated imine products and subsequent reduction to the corresponding N-alkyl delta,epsilon-unsaturated amines is reported. Several routes to the N-allyl-N-isobutyl enamines were established for the enamine prepared from isobutyraldehyde. With use of the most efficient route developed, enamines derived from butanal, 2-phenylpropanal, cyclohexanone, and cyclopentanone were prepared in 58 to 92% overall yield in three steps from allylamine. In the case of butanal, the E isomer was formed exclusively, while the enamine from 2-phenylpropanal was prepared with an E to Z selectivity of 86:14. Heating these N-allyl-N-isobutyl enamines in refluxing dioxane with 0.5 equiv of HCl produced [3,3] rearrangement for substrates derived from isobutyraldehyde, 2-phenylpropanal, and cyclohexanone; the enamines of n-butanal and cyclopentanone were found to react through alternate pathways.

  DOI：

  10.1021/jo00019a021