(4RS,5S)-3-ethoxycarbonyl-4-hydroxy-5-(4-pentenyl)-2-isoxazoline 2-oxide | 216855-26-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4RS,5S)-3-ethoxycarbonyl-4-hydroxy-5-(4-pentenyl)-2-isoxazoline 2-oxide
• 英文别名: ethyl (5S)-4-hydroxy-2-oxido-5-pent-4-enyl-4,5-dihydro-1,2-oxazol-2-ium-3-carboxylate
• CAS: 216855-26-4
• 化学式: C₁₁H₁₇NO₅
• 分子量: 243.26
• InChiKey: LVZMPKRVSNGUGH-PEHGTWAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  81.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  二甲基乙烯基氯硅烷 、 (4RS,5S)-3-ethoxycarbonyl-4-hydroxy-5-(4-pentenyl)-2-isoxazoline 2-oxide 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 ethyl (2aR,6S,6aS,6bR)-2,2-dimethyl-6-(4-pentenyl)tetrahydro-2H,6bH-1,4,5-trioxa-4a-aza-2-silacyclopenta[cd]pentalene-6b-carboxylate 、 ethyl (2aS,6S,6aR,6bS)-2,2-dimethyl-6-(4-pentenyl)tetrahydro-2H,6bH-1,4,5-trioxa-4a-aza-2-silacyclopenta[cd]pentalene-6b-carboxylate
  参考文献：
  名称：

  d-Mannitol as the Chiral Source for the EPC Synthesis of Both Enantiomers of 3-Ethoxycarbonyl-4-hydroxy-2-isoxazolines and Highly Functionalized Tricyclic Systems

  摘要：

  The EPC preparation of both enantiomers of cis- and trans 5-substituted 4-hydroxy-2-isoxazoline 2-oxides has been achieved in an enantiodivergent fashion starting from D-mannitol through the application of the tandem nitroaldol-cyclization reaction to enantiomerically pure alpha-mesyloxyaldehydes. These stereochemically labile aldehydes have been generated in situ and reacted under very mild domino conditions. Enantiomeric purity of the products has been assessed by H-1 NMR and HPLC analyses of the corresponding Mosher's esters. The enantiomerically pure 4-hydroxy-2-isoxazoline a-oxides have been employed as pivotal intermediates for the EPC preparation of the corresponding deoxygenated derivatives and highly functionalized tricyclic systems (HFTS) 1, useful for the preparation of 2-aminopolyols and alpha,alpha-disubstituted polyhydroxy amino acids.

  DOI：

  10.1021/jo980941i
• 作为产物：
  描述：

  (6R,7R,8R,9R)-7,8-O-isopropylidenetetradecane-1,13-diene-6,7,8,9-tetraol 在 吡啶 、 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 sodium periodate 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 (4RS,5S)-3-ethoxycarbonyl-4-hydroxy-5-(4-pentenyl)-2-isoxazoline 2-oxide
  参考文献：
  名称：

  d-Mannitol as the Chiral Source for the EPC Synthesis of Both Enantiomers of 3-Ethoxycarbonyl-4-hydroxy-2-isoxazolines and Highly Functionalized Tricyclic Systems

  摘要：

  The EPC preparation of both enantiomers of cis- and trans 5-substituted 4-hydroxy-2-isoxazoline 2-oxides has been achieved in an enantiodivergent fashion starting from D-mannitol through the application of the tandem nitroaldol-cyclization reaction to enantiomerically pure alpha-mesyloxyaldehydes. These stereochemically labile aldehydes have been generated in situ and reacted under very mild domino conditions. Enantiomeric purity of the products has been assessed by H-1 NMR and HPLC analyses of the corresponding Mosher's esters. The enantiomerically pure 4-hydroxy-2-isoxazoline a-oxides have been employed as pivotal intermediates for the EPC preparation of the corresponding deoxygenated derivatives and highly functionalized tricyclic systems (HFTS) 1, useful for the preparation of 2-aminopolyols and alpha,alpha-disubstituted polyhydroxy amino acids.

  DOI：

  10.1021/jo980941i