ethyl 7-(trimethylsilyloxy)-1,4-dioxaspiro[4.5]dec-7-ene-8-carboxylate | 1356487-24-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 7-(trimethylsilyloxy)-1,4-dioxaspiro[4.5]dec-7-ene-8-carboxylate
• CAS: 1356487-24-5
• 化学式: C₁₄H₂₄O₅Si
• 分子量: 300.427
• InChiKey: LAOXSIOZOFQBIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 7-(trimethylsilyloxy)-1,4-dioxaspiro[4.5]dec-7-ene-8-carboxylate 在 正丁基锂 、 甲基三氯硅烷 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.42h， 生成 (1SR,5SR)-ethyl 3-ethyl-9-methylen-3-azaspiro[bicyclo[3.3.1]nonane-6,2'-[1,3]dioxolane]-1-carboxylate
  参考文献：
  名称：

  An efficient synthesis of 3-alkyl-1,5,3-dioxazepanes and their use as electrophiles in double-Mannich reactions

  摘要：

  An efficient synthesis of 3-alkyl 1,5,3-dioxazepanes was developed for subsequent use in double-Mannich reactions with a variety of carbon-based nucleophiles. It was found that addition of methyltrichlorosilane to the dioxazepane led to a long-lasting reactive species that reacted rapidly with acid-sensitive ketones and beta-ketoesters to afford azabicyclo[3.3.1]nonanes in good yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.090
• 作为产物：
  描述：

  丁酰丙二酸二乙酯 在 sodium ethanolate 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 19.0h， 生成 ethyl 7-(trimethylsilyloxy)-1,4-dioxaspiro[4.5]dec-7-ene-8-carboxylate
  参考文献：
  名称：

  An efficient synthesis of 3-alkyl-1,5,3-dioxazepanes and their use as electrophiles in double-Mannich reactions

  摘要：

  An efficient synthesis of 3-alkyl 1,5,3-dioxazepanes was developed for subsequent use in double-Mannich reactions with a variety of carbon-based nucleophiles. It was found that addition of methyltrichlorosilane to the dioxazepane led to a long-lasting reactive species that reacted rapidly with acid-sensitive ketones and beta-ketoesters to afford azabicyclo[3.3.1]nonanes in good yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.090