ethyl 7-(tert-butyldimethylsilyloxy)-8-nonen-2-ynoate | 1612771-26-2

• 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: ethyl 7-(tert-butyldimethylsilyloxy)-8-nonen-2-ynoate
• 英文别名: Ethyl 7-[tert-butyl(dimethyl)silyl]oxynon-8-en-2-ynoate
• CAS: 1612771-26-2
• 化学式: C₁₇H₃₀O₃Si
• 分子量: 310.509
• InChiKey: DHQPTAVMPOGJJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 7-(tert-butyldimethylsilyloxy)-8-nonen-2-ynoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以47%的产率得到ethyl 2-(2-vinyl-3,4-dihydro-2H-pyran-6-yl)ethanoate
  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 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 ethyl 7-(tert-butyldimethylsilyloxy)-8-nonen-2-ynoate
  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