4-hydroxy-5-hydroxymethyl-2-oxy-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester | 332080-19-0

• 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: 4-hydroxy-5-hydroxymethyl-2-oxy-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester
• CAS: 332080-19-0
• 化学式: C₇H₁₁NO₆
• 分子量: 205.167
• InChiKey: RTFJQGBTUZLBFV-VKZKZBKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.83
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  102.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5-hydroxymethyl-2-oxy-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester 在 三甲氧基磷 作用下， 生成 (4S,5S)-4-tert-butyldimethylsilyloxy-5-tert-butyldimethylsilyloxymethyl-3-ethoxycarbonyl-4,5-dihydroisoxazole
  参考文献：
  名称：

  One-Pot Direct Conversion of 2,3-Epoxy Alcohols into Enantiomerically Pure 4-Hydroxy-4,5-dihydroisoxazole 2-Oxides

  摘要：

  [GRAPHICS]A new methodology for the one-pot direct conversion of 2,3-epoxy alcohols into enantiomerically pure 4-hydroxy-4,5-dihydroisoxazole P-oxides 1 has been found. The reaction works at room temperature and can be run at the 5-10 g scale. The mixture of 4,5-cis and 4,5-trans isomers obtained can be separated as such or as the bis-TDS ethers, A preliminary example of reductive cleavage of 1 to the corresponding amino polyol is also reported.

  DOI：

  10.1021/ol0070379
• 作为产物：
  描述：

  硝基乙酸乙酯 、 (R)-glycidaldehyde 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 4-hydroxy-5-hydroxymethyl-2-oxy-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  One-Pot Direct Conversion of 2,3-Epoxy Alcohols into Enantiomerically Pure 4-Hydroxy-4,5-dihydroisoxazole 2-Oxides

  摘要：

  [GRAPHICS]A new methodology for the one-pot direct conversion of 2,3-epoxy alcohols into enantiomerically pure 4-hydroxy-4,5-dihydroisoxazole P-oxides 1 has been found. The reaction works at room temperature and can be run at the 5-10 g scale. The mixture of 4,5-cis and 4,5-trans isomers obtained can be separated as such or as the bis-TDS ethers, A preliminary example of reductive cleavage of 1 to the corresponding amino polyol is also reported.

  DOI：

  10.1021/ol0070379