Isobutyl-[2-(1-vinyl-pentyl)-cyclohexyl]-amine | 144608-92-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Isobutyl-[2-(1-vinyl-pentyl)-cyclohexyl]-amine
• 英文别名: 2-hept-1-en-3-yl-N-(2-methylpropyl)cyclohexan-1-amine
• CAS: 144608-92-4
• 化学式: C₁₇H₃₃N
• 分子量: 251.456
• InChiKey: IYSCTZWTUDLVMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  Isobutyl-[2-(1-vinyl-pentyl)-cyclohex-(E)-ylidene]-amine 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 24.0h， 生成 Isobutyl-[2-(1-vinyl-pentyl)-cyclohexyl]-amine
  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

• Stereochemical consequences of the lewis acid-promoted 3-aza-cope rearrangement of N-alkyl-N-allyl enamines
  作者：Ggregory R. Cook、John R. Stille

  DOI：10.1016/s0040-4020(01)86707-7

  日期：1994.4

  Internal and relative asymmetric induction were examined for the electrophile promoted 3-aza-Cope rearrangement of substituted N-alkyl-N-allyl enamines. In general, internal asymmetric induction was highly variable, and was dependent both upon the nature of the electrophilic reagent and substrate. However, substitution at C-4 of the substrate served to anchor the transition state of the substrates

  检查了内部和相对不对称诱导的亲电试剂促进的取代的N-烷基-N-烯丙基烯胺的3-氮杂-Cope重排。通常，内部不对称感应是高度可变的，并且取决于亲电子试剂和底物的性质。然而，在底物的C-4处的取代起到锚定底物的过渡态的作用，并且产物选择性通常> 95：5。当N-烷基取代基被束缚到C-4时，获得了从五元环到九元环的扩环。
• 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.