(2R)-2-methyloxirane-2-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2R)-2-methyloxirane-2-carbaldehyde
• 化学式: C₄H₆O₂
• 分子量: 86.0904
• InChiKey: ARDBEZFTUVBDOJ-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  6.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  硝基乙酸乙酯 、 (2R)-2-methyloxirane-2-carbaldehyde 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 4-hydroxy-5-hydroxymethyl-5-methyl-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
• 作为产物：
  描述：

  (S)-2-甲基缩水甘油 在 碘苯二乙酸 、 tetramethylpiperidinyloxy radical 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2R)-2-methyloxirane-2-carbaldehyde
  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

文献信息

• One-Pot Direct Conversion of 2,3-Epoxy Alcohols into Enantiomerically Pure 4-Hydroxy-4,5-dihydroisoxazole 2-Oxides
  作者：Emanuela Marotta、Laure Marie Micheloni、Noemi Scardovi、Paolo Righi

  DOI：10.1021/ol0070379

  日期：2001.3.1

  [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.