4-(5-(2-hydroxy-3-butenyl)-2,2-dimethyl-1,3-dioxan-5-yl)but-2-ynenitrile | 1612771-36-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(5-(2-hydroxy-3-butenyl)-2,2-dimethyl-1,3-dioxan-5-yl)but-2-ynenitrile
• 英文别名: 4-[5-(2-Hydroxybut-3-enyl)-2,2-dimethyl-1,3-dioxan-5-yl]but-2-ynenitrile；4-[5-(2-hydroxybut-3-enyl)-2,2-dimethyl-1,3-dioxan-5-yl]but-2-ynenitrile
• CAS: 1612771-36-4
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: XLQUPWRSYRENHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 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：
  62.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(5-(2-hydroxy-3-butenyl)-2,2-dimethyl-1,3-dioxan-5-yl)but-2-ynenitrile 在 lithium hexamethyldisilazane 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.0h， 以79%的产率得到3,3-dimethyl-8-oxo-2,4-dioxaspiro[5.7]tridec-11-ene-9-carbonitrile
  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：

  5-allyl-2,2-dimethyl-5-(prop-2-yn-1-yl)-1,3-dioxane 在 sodium periodate 、 四氧化锇 、 正丁基锂 、 silica gel 、 N-甲基吗啉氧化物 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 8.75h， 生成 4-(5-(2-hydroxy-3-butenyl)-2,2-dimethyl-1,3-dioxan-5-yl)but-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