(3S,4S,7S,9S,10R)-9-phenyl-3-prop-2-enoxy-5-oxa-1-azatricyclo[5.2.1.04,10]decane | 144866-77-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3S,4S,7S,9S,10R)-9-phenyl-3-prop-2-enoxy-5-oxa-1-azatricyclo[5.2.1.04,10]decane
• CAS: 144866-77-3
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: CQCPQQYZQXXLOG-DRRXZNNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3S,4S)-1-苄基吡咯烷-3,4-二醇 在 叔丁基过氧化氢 、 vanadyl acetylacetonate 、 四丁基碘化铵 、 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S,4S,7S,9S,10R)-9-phenyl-3-prop-2-enoxy-5-oxa-1-azatricyclo[5.2.1.04,10]decane
  参考文献：
  名称：

  First Example of Intramolecular 1,3-Dipolar Cycloaddition of Non-stabilized Azomethine Ylide Generated from Tertiary Amine N-Oxide

  摘要：

  The reaction of two optically active 1-alkyl-3,4-diallyloxypyrrolidine 1-oxides, (9) and (15), under basic conditions has been examined. The 1-benzyl derivative (9), on reaction with lithium diisopropylamide, furnished a single pyrrolidine derivative (11) by intramolecular 1,3-dipolar cycloaddition of an N-benzylidene azomethine ylide (10), while the 1-methyl derivative (15) reacted with tert-butyllithium in the presence of trimethylaluminum to afford only a single 7-azabicyclo[2.2.1]heptane derivative (19) by spontaneous intramolecular 1,3-dipolar cycloaddition of the endocyclic azomethine ylide (17).

  DOI：

  10.3987/com-92-6107

文献信息

• First Example of Intramolecular 1,3-Dipolar Cycloaddition of Non-stabilized Azomethine Ylide Generated from Tertiary Amine N-Oxide
  作者：Seiichi Takano、Yoshiaki Sugihara、Kunio Ogasawara

  DOI：10.3987/com-92-6107

  日期：——

  The reaction of two optically active 1-alkyl-3,4-diallyloxypyrrolidine 1-oxides, (9) and (15), under basic conditions has been examined. The 1-benzyl derivative (9), on reaction with lithium diisopropylamide, furnished a single pyrrolidine derivative (11) by intramolecular 1,3-dipolar cycloaddition of an N-benzylidene azomethine ylide (10), while the 1-methyl derivative (15) reacted with tert-butyllithium in the presence of trimethylaluminum to afford only a single 7-azabicyclo[2.2.1]heptane derivative (19) by spontaneous intramolecular 1,3-dipolar cycloaddition of the endocyclic azomethine ylide (17).