(4S,5R)-3,4-dimethyl-5-phenylimidazolidin-2-one-1-carbohydroxamic acid | 158267-02-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5R)-3,4-dimethyl-5-phenylimidazolidin-2-one-1-carbohydroxamic acid
• CAS: 158267-02-8
• 化学式: C₁₂H₁₅N₃O₃
• 分子量: 249.269
• InChiKey: GJKXOIZDEKNFHO-WPRPVWTQSA-N

物化性质

• 密度：
  1.294±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.88
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-3,4-dimethyl-5-phenylimidazolidin-2-one-1-carbohydroxamic acid 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Diastereoselective hetero-diels-alder cycloaddition of a C-nitroso compound prepared starting from a homochiral imidazolidin-2-one

  摘要：

  By Swern oxidation of the hydroxamic acid 3, prepared from the homochiral imidazolidin-2-one 1, the transient C-nitroso derivative 4 is obtained, and its cycloaddition to either cyclohexadiene or cyclopentadiene proceeds with high diastereoselection, owing to the conformational stability of 4. The stereochemical outcome of the reaction is determined from H-1 NMR data and further confirmed by the specific rotation value of 7, obtained by cleavage of the major cycloadduct 5a.

  DOI：

  10.1016/0957-4166(94)80123-1
• 作为产物：
  描述：

  (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one 在 sodium hydroxide 、 正丁基锂 、 盐酸羟胺 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 (4S,5R)-3,4-dimethyl-5-phenylimidazolidin-2-one-1-carbohydroxamic acid
  参考文献：
  名称：

  Diastereoselective hetero-diels-alder cycloaddition of a C-nitroso compound prepared starting from a homochiral imidazolidin-2-one

  摘要：

  By Swern oxidation of the hydroxamic acid 3, prepared from the homochiral imidazolidin-2-one 1, the transient C-nitroso derivative 4 is obtained, and its cycloaddition to either cyclohexadiene or cyclopentadiene proceeds with high diastereoselection, owing to the conformational stability of 4. The stereochemical outcome of the reaction is determined from H-1 NMR data and further confirmed by the specific rotation value of 7, obtained by cleavage of the major cycloadduct 5a.

  DOI：

  10.1016/0957-4166(94)80123-1