1-[(1S,2R)-2-exo-methoxyapocamphanecarbonyl]-2-imidazolone

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-[(1S,2R)-2-exo-methoxyapocamphanecarbonyl]-2-imidazolone
• 英文别名: 3-[(1S,2R,4R)-2-methoxy-7,7-dimethylbicyclo[2.2.1]heptane-1-carbonyl]-1H-imidazol-2-one
• 化学式: C₁₄H₂₀N₂O₃
• 分子量: 264.324
• InChiKey: RZTCLYUXFVGIGO-RULNRJAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(1S,2R)-2-exo-methoxyapocamphanecarbonyl]-2-imidazolone 在 吡啶-2,6-二甲酸 、 三氟化硼乙醚 、 Fe⁽³⁺⁾*Cl^(1-)*2H₂O*C₇H₃NO₄^(2-) 、 双氧水 、 二异丙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 11.5h， 生成
  参考文献：
  名称：

  Efficient Preparation of a Versatile Chiral Synthon for 1,2-Diamines via the Fe(III)-Catalyzed Diastereoselective Oxidation of 2-Imidazolone and Its Application

  摘要：

  The efficient and predominant preparation of (4S,5S)-4,5-dimethoxy-2-imidazolidinone (DMIm) was established via the Fe(III)-catalyzed diastereoselective oxidation of 1-[(1S,2R)-2-exo-alkoxyapocamphanecarbonyl]-2-imidazolone with aqueous H2O2 up to 94% d.e., both of which were easily purified by column chromatography, followed by simple and convenient conversions. The obtained N-tosyl-(4S,5S)-DMIm proved to be a versatile chiral synthon for 1,2-diamines by the synthesis of (1S,2S)-1,2-diamino-1-(4-fluorophenyl)butane derivative, whose platinum complex showed potent antitumor activity.

  DOI：

  10.3987/com-14-s(k)96

文献信息

• Efficient Preparation of a Versatile Chiral Synthon for 1,2-Diamines via the Fe(III)-Catalyzed Diastereoselective Oxidation of 2-Imidazolone and Its Application
  作者：Hirofumi Matsunaga、Tadao Ishizuka、Iori Eshita、Shin Ando

  DOI：10.3987/com-14-s(k)96

  日期：——

  The efficient and predominant preparation of (4S,5S)-4,5-dimethoxy-2-imidazolidinone (DMIm) was established via the Fe(III)-catalyzed diastereoselective oxidation of 1-[(1S,2R)-2-exo-alkoxyapocamphanecarbonyl]-2-imidazolone with aqueous H2O2 up to 94% d.e., both of which were easily purified by column chromatography, followed by simple and convenient conversions. The obtained N-tosyl-(4S,5S)-DMIm proved to be a versatile chiral synthon for 1,2-diamines by the synthesis of (1S,2S)-1,2-diamino-1-(4-fluorophenyl)butane derivative, whose platinum complex showed potent antitumor activity.