1-azido-hex-4-yn-3-ol | 851113-01-4

• 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-hex-4-yn-3-ol
• 英文别名: 1-Azidohex-4-YN-3-OL；1-azidohex-4-yn-3-ol
• CAS: 851113-01-4
• 化学式: C₆H₉N₃O
• 分子量: 139.157
• InChiKey: BBJTVDLOHSCSJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-azido-hex-4-yn-3-ol 在 四(三苯基膦)钯 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氘代甲苯 为溶剂， 反应 22.5h， 生成 (3aS,4R,6aS)-6a-Cyano-6-methyl-1,2,3,3a,4,6a-hexahydro-cyclopenta[b]pyrrole-4-carboxylic acid ethyl ester
  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
• 作为产物：
  描述：

  3-叠氮丙醛 、 1-丙炔溴化镁 以 四氢呋喃 为溶剂， 反应 2.5h， 以65%的产率得到1-azido-hex-4-yn-3-ol
  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

文献信息

• Allenyl Azide Cycloaddition Chemistry: Exploration of the Scope and Mechanism of Cyclopentennelated Dihydropyrrole Synthesis through Azatrimethylenemethane Intermediates
  作者：Ken S. Feldman、Malliga R. Iyer、Carlos Silva López、Olalla Nieto Faza

  DOI：10.1021/jo8008066

  日期：2008.7.1

  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.
• Allenyl Azide Cycloaddition Chemistry. Synthesis of Pyrrolidine-Containing Bicycles and Tricycles via the Possible Intermediacy of Azatrimethylenemethane Species
  作者：Ken S. Feldman、Malliga R. Iyer

  DOI：10.1021/ja050757w

  日期：2005.4.1

  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.