1-azido-6-methylhepta-3,4,7-triene | 851113-08-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-azido-6-methylhepta-3,4,7-triene
• CAS: 851113-08-1
• 化学式: C₈H₁₁N₃
• 分子量: 149.195
• InChiKey: NLBLZOKOIMXCRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三甲基氰硅烷 、 1-azido-6-methylhepta-3,4,7-triene 以 氘代甲苯 、 二氯甲烷 为溶剂， 反应 17.0h， 以96%的产率得到(3aR,6aS)-6-Methyl-2,3,3a,4-tetrahydro-1H-cyclopenta[b]pyrrole-6a-carbonitrile
  参考文献：
  名称：

  Allenyl Azide Cycloaddition Chemistry: Exploration of the Scope and Mechanism of Cyclopentennelated Dihydropyrrole Synthesis through Azatrimethylenemethane Intermediates

  摘要：

  Detailed studies of the thermal conversion of 1-azidohepta-3,4,6-trienes into cyclopentennelated dihydropyrroles are presented. High levels of diastereoselectivity and regioselectivity are documented. A mechanistic proposal that accounts for all of the diverse results is developed through the use of density functional calculations. These calculations provide support for the intervention of unexpected mechanistic subtleties, such as the planarity of an azatrimethylenemethane diyl intermediate and an apparent Woodward-Hoffmann-type electrocyclization of a five-atom diyl array.

  DOI：

  10.1021/jo8008066
• 作为产物：
  描述：

  1-azido-hex-4-yn-3-ol 在 三乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 1-azido-6-methylhepta-3,4,7-triene
  参考文献：
  名称：

  Allenyl Azide Cycloaddition Chemistry. Synthesis of Pyrrolidine-Containing Bicycles and Tricycles via the Possible Intermediacy of Azatrimethylenemethane Species

  摘要：

  Thermolysis of 5-azidoallenes bearing a C(1) methyl group and either an aryl ring or an alkene on C(1) furnishes tricyclic (from the aryl substrates) or bicyclic (from the alkenyl substrates) pyrrolidine products following formal H-CN addition across an intermediate imine. High levels of diastereoselectivity are observed in all cases studied. This reaction cascade presumably passes through unobserved triazoline and azatrimethylenemethane diyl intermediates en route to product.

  DOI：

  10.1021/ja050757w