4-((S)-5-Phenoxymethyl-3-trimethylsilanyl-4,5-dihydro-furan-2-yl)-morpholine | 415902-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-((S)-5-Phenoxymethyl-3-trimethylsilanyl-4,5-dihydro-furan-2-yl)-morpholine
• 英文别名: trimethyl-[(2S)-5-morpholin-4-yl-2-(phenoxymethyl)-2,3-dihydrofuran-4-yl]silane
• CAS: 415902-43-1
• 化学式: C₁₈H₂₇NO₃Si
• 分子量: 333.503
• InChiKey: MHNXIIQZBSTBGB-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((S)-5-Phenoxymethyl-3-trimethylsilanyl-4,5-dihydro-furan-2-yl)-morpholine 在 potassium hydrogen difluoride 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以59 mg的产率得到(S)-5-Phenoxymethyl-dihydro-furan-2-one
  参考文献：
  名称：

  A Direct Method for the Conversion of Terminal Epoxides into γ-Butanolides

  摘要：

  A new and efficient process for the conversion of terminal epoxides to gamma-butanolides is described involving Lewis acid promoted epoxide ring-opening by 1-morpholino-2-trimethylsilyl acetylene. Addition of a terminal epoxide to a solution of the ynamine and boron trifluoride diethyl etherate in dichloromethane at 0 degrees C rapidly affords a cyclic keteneaminal that can be hydrolyzed and protodesilylated under mild conditions to provide the corresponding gamma-butanolide in high yield. The net transformation is equivalent to an acetate enolate opening of terminal epoxides. The formation of a cyclic keteneaminal as the direct addition product was observed by monitoring of the reaction by IR and NMR spectroscopy. Functionalized gamma-lactones were prepared by the interception of the reactive cyclic keteneaminal prior to hydrolysis. Reactions with enantiomerically enriched terminal epoxides provide the corresponding gamma-butanolides without loss of optical activity. The compatibility of the present methodology with a wide range of functional groups is noteworthy.

  DOI：

  10.1021/ja025604c
• 作为产物：
  描述：

  1,1,2-Trichloro-2-morpholinoethen 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 4-((S)-5-Phenoxymethyl-3-trimethylsilanyl-4,5-dihydro-furan-2-yl)-morpholine
  参考文献：
  名称：

  A Direct Method for the Conversion of Terminal Epoxides into γ-Butanolides

  摘要：

  A new and efficient process for the conversion of terminal epoxides to gamma-butanolides is described involving Lewis acid promoted epoxide ring-opening by 1-morpholino-2-trimethylsilyl acetylene. Addition of a terminal epoxide to a solution of the ynamine and boron trifluoride diethyl etherate in dichloromethane at 0 degrees C rapidly affords a cyclic keteneaminal that can be hydrolyzed and protodesilylated under mild conditions to provide the corresponding gamma-butanolide in high yield. The net transformation is equivalent to an acetate enolate opening of terminal epoxides. The formation of a cyclic keteneaminal as the direct addition product was observed by monitoring of the reaction by IR and NMR spectroscopy. Functionalized gamma-lactones were prepared by the interception of the reactive cyclic keteneaminal prior to hydrolysis. Reactions with enantiomerically enriched terminal epoxides provide the corresponding gamma-butanolides without loss of optical activity. The compatibility of the present methodology with a wide range of functional groups is noteworthy.

  DOI：

  10.1021/ja025604c