1-(1-cyclopentenyl)-5-hexyn-1-ol | 1612771-48-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-(1-cyclopentenyl)-5-hexyn-1-ol
• 英文别名: 1-(Cyclopenten-1-yl)hex-5-yn-1-ol；1-(cyclopenten-1-yl)hex-5-yn-1-ol
• CAS: 1612771-48-8
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: LLWQJJQCCWYXKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1-cyclopentenyl)-5-hexyn-1-ol 在 正丁基锂 、 氢氟酸 作用下， 以 乙醚 、 水 为溶剂， 反应 3.5h， 生成 7-(1-cyclopentenyl)-7-hydroxyhept-2-ynenitrile
  参考文献：
  名称：

  Facile access to cyclooctanoid ring systems via microwave-assisted tandem 6-exo dig cyclization–rearrangement sequence

  摘要：

  Appropriately substituted 5-alkyn-1-ol systems bearing a nitrile moiety at the triple bond serve as versatile precursors to a variety of cyclooctenone derivatives via a "one-pot" base-catalyzed oxyanionic 6-exo dig cyclization/Claisen rearrangement sequence under microwave irradiation. It was found that the initially formed cyclic intermediate consists of a mixture of endo and exocyclic isomers, which appear to be in equilibrium under the reaction conditions. However, the only observed products from these reactions are α-cyano substituted cyclooctenones, derived from the exocyclic dihydrofuran intermediates.

  DOI：

  10.1016/j.tet.2014.02.089
• 作为产物：
  描述：

  6-三甲基硅烷基-己-5-炔-1-醇 在 四丁基氟化铵 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.08h， 生成 1-(1-cyclopentenyl)-5-hexyn-1-ol
  参考文献：
  名称：

  Facile access to cyclooctanoid ring systems via microwave-assisted tandem 6-exo dig cyclization–rearrangement sequence

  摘要：

  Appropriately substituted 5-alkyn-1-ol systems bearing a nitrile moiety at the triple bond serve as versatile precursors to a variety of cyclooctenone derivatives via a "one-pot" base-catalyzed oxyanionic 6-exo dig cyclization/Claisen rearrangement sequence under microwave irradiation. It was found that the initially formed cyclic intermediate consists of a mixture of endo and exocyclic isomers, which appear to be in equilibrium under the reaction conditions. However, the only observed products from these reactions are α-cyano substituted cyclooctenones, derived from the exocyclic dihydrofuran intermediates.

  DOI：

  10.1016/j.tet.2014.02.089

文献信息

• Facile access to cyclooctanoid ring systems via microwave-assisted tandem 6-exo dig cyclization–rearrangement sequence
  作者：Aaron W. Feldman、Sami I. Ovaska、Timo V. Ovaska

  DOI：10.1016/j.tet.2014.02.089

  日期：2014.7

  Appropriately substituted 5-alkyn-1-ol systems bearing a nitrile moiety at the triple bond serve as versatile precursors to a variety of cyclooctenone derivatives via a "one-pot" base-catalyzed oxyanionic 6-exo dig cyclization/Claisen rearrangement sequence under microwave irradiation. It was found that the initially formed cyclic intermediate consists of a mixture of endo and exocyclic isomers, which appear to be in equilibrium under the reaction conditions. However, the only observed products from these reactions are α-cyano substituted cyclooctenones, derived from the exocyclic dihydrofuran intermediates.