(3S,4S)-1-methyl-1-oxido-3,4-bis(prop-2-enoxy)pyrrolidin-1-ium | 144866-80-8

• 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)-1-methyl-1-oxido-3,4-bis(prop-2-enoxy)pyrrolidin-1-ium
• CAS: 144866-80-8
• 化学式: C₁₁H₁₉NO₃
• 分子量: 213.277
• InChiKey: PZLVELROSUFDAL-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  36.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-1-methyl-1-oxido-3,4-bis(prop-2-enoxy)pyrrolidin-1-ium 在 三甲基铝 、 叔丁基锂 作用下， 生成 (1S,2S,3S,6S,7R)-8-methyl-4-oxa-8-azatricyclo[4.2.1.03,7]nonan-2-ol
  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
• 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 、 lithium aluminium tetrahydride 、 bis(acetylacetonate)oxovanadium 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 (3S,4S)-1-methyl-1-oxido-3,4-bis(prop-2-enoxy)pyrrolidin-1-ium
  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).