3,3,11-trimethyl-8-oxo-2,4-dioxaspiro[5.7]tridec-11-ene-9-carbonitrile | 1612771-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3,11-trimethyl-8-oxo-2,4-dioxaspiro[5.7]tridec-11-ene-9-carbonitrile
• CAS: 1612771-41-1
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: FRLFAOAVFGBOAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  59.32
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-(5-(2-hydroxy-3-methylbut-3-en-1-yl)-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84%的产率得到3,3,11-trimethyl-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