(2R,3aS,6S)-6-tert-butyl-2,5-dimethyl-4-oxo-hexahydroimidazo[1,5-b]isoxazole-2-carboxylic acid methyl ester | 699432-76-3

• 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: (2R,3aS,6S)-6-tert-butyl-2,5-dimethyl-4-oxo-hexahydroimidazo[1,5-b]isoxazole-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3aS,6S)-6-tert-butyl-2,5-dimethyl-4-oxo-3a,6-dihydro-3H-imidazo[1,5-b][1,2]oxazole-2-carboxylate
• CAS: 699432-76-3
• 化学式: C₁₃H₂₂N₂O₄
• 分子量: 270.329
• InChiKey: OLJQQDGCEAMIKI-GMOODISLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3aS,6S)-6-tert-butyl-2,5-dimethyl-4-oxo-hexahydroimidazo[1,5-b]isoxazole-2-carboxylic acid methyl ester 在 palladium on activated charcoal 盐酸 、 ammonium formate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 (2S,4R)-2-amino-4-hydroxy-4-methylpentanedioic acid lactone hydrochloride
  参考文献：
  名称：

  2-tert-Butyl-3-methyl-2,3-dihydroimidazol- 4-one-N-oxide:  A New Nitrone-Based Chiral Glycine Equivalent

  摘要：

  Cycloaddition reactions between a new homochiral imidazolone-derived nitrone afford cycloadclucts in high yield and with high stereoselectivity. Subsequent cycloadduct elaboration affords the gamma-lactones of gamma-hydroxy-alpha-amino acids as well as the optically pure amino acids themselves.

  DOI：

  10.1021/ol049505a
• 作为产物：
  描述：

  (2R)-2-(tert-butyl)-3-methylimidazolidin-4-one 在 urea-hydrogen peroxide 、 甲基三氧化铼(VII) 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 29.5h， 生成 (2R,3aS,6S)-6-tert-butyl-2,5-dimethyl-4-oxo-hexahydroimidazo[1,5-b]isoxazole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  2-tert-Butyl-3-methyl-2,3-dihydroimidazol- 4-one-N-oxide:  A New Nitrone-Based Chiral Glycine Equivalent

  摘要：

  Cycloaddition reactions between a new homochiral imidazolone-derived nitrone afford cycloadclucts in high yield and with high stereoselectivity. Subsequent cycloadduct elaboration affords the gamma-lactones of gamma-hydroxy-alpha-amino acids as well as the optically pure amino acids themselves.

  DOI：

  10.1021/ol049505a

文献信息

• 2-<i>tert</i>-Butyl-3-methyl-2,3-dihydroimidazol- 4-one-<i>N</i>-oxide:  A New Nitrone-Based Chiral Glycine Equivalent
  作者：Steven W. Baldwin、Alan Long

  DOI：10.1021/ol049505a

  日期：2004.5.1

  Cycloaddition reactions between a new homochiral imidazolone-derived nitrone afford cycloadclucts in high yield and with high stereoselectivity. Subsequent cycloadduct elaboration affords the gamma-lactones of gamma-hydroxy-alpha-amino acids as well as the optically pure amino acids themselves.