(E)-1-(N-(2-methylprop-1-yl)amino)-2,2-dimethyl-4-octene | 144608-85-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-1-(N-(2-methylprop-1-yl)amino)-2,2-dimethyl-4-octene
• 英文别名: (E)-2,2-dimethyl-N-(2-methylpropyl)oct-4-en-1-amine
• CAS: 144608-85-5
• 化学式: C₁₄H₂₉N
• 分子量: 211.391
• InChiKey: PTWZTBWDIVSIBO-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  己-1-烯-3-胺 在 三甲基铝 、 对甲苯磺酸 lithium aluminium tetrahydride 、 三甲基铝 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 37.0h， 生成 (E)-1-(N-(2-methylprop-1-yl)amino)-2,2-dimethyl-4-octene
  参考文献：
  名称：

  Studies of the regiospecific 3-aza-Cope rearrangement promoted by electrophilic reagents

  摘要：

  The 3-aza-Cope rearrangement of N-alkyl-N-allyl enamine substrates, which required temperatures of 250 250-degrees-C to proceed thermally, was promoted at 111-degrees-C in the presence of electrophilic reagents such as HCl (0.5 equiv) TiCl4 (0.2 equiv), AlMe3 (1.2 equiv), or (ArO)2AlMe (1.2 equiv). In order to probe the regioselectivity of this accelerated carbon-carbon bond forming process under these reaction conditions, several enamine substrates were prepared from both isobutyraldehyde and cyclohexanone. Each substrate used in these studies was prepared having an unsymmetrical N-allylic group, substituted with either an alkyl or phenyl substituent at the 4 or 6 position of the 3-aza-Cope framework. In all cam examined, reaction acceleration by the electrophilic reagent produced regiospecific [3,3] rearrangement to the corresponding products resulting from [1,3] rearrangement were not observed. Hydride reduction of the resulting imines generated the delta,epsilon-unsaturated amines in 55-94% overall yield in the three-step condensation-rearrangement-reduction process from the secondary allylamine.

  DOI：

  10.1021/jo00052a037

文献信息

• Studies of the regiospecific 3-aza-Cope rearrangement promoted by electrophilic reagents
  作者：Nancy S. Barta、Gregory R. Cook、Margaret S. Landis、John R. Stille

  DOI：10.1021/jo00052a037

  日期：1992.12

  The 3-aza-Cope rearrangement of N-alkyl-N-allyl enamine substrates, which required temperatures of 250 250-degrees-C to proceed thermally, was promoted at 111-degrees-C in the presence of electrophilic reagents such as HCl (0.5 equiv) TiCl4 (0.2 equiv), AlMe3 (1.2 equiv), or (ArO)2AlMe (1.2 equiv). In order to probe the regioselectivity of this accelerated carbon-carbon bond forming process under these reaction conditions, several enamine substrates were prepared from both isobutyraldehyde and cyclohexanone. Each substrate used in these studies was prepared having an unsymmetrical N-allylic group, substituted with either an alkyl or phenyl substituent at the 4 or 6 position of the 3-aza-Cope framework. In all cam examined, reaction acceleration by the electrophilic reagent produced regiospecific [3,3] rearrangement to the corresponding products resulting from [1,3] rearrangement were not observed. Hydride reduction of the resulting imines generated the delta,epsilon-unsaturated amines in 55-94% overall yield in the three-step condensation-rearrangement-reduction process from the secondary allylamine.