(5R)-5-(1,3-benzodioxol-5-ylmethyl)-5-methylimidazolidine-2,4-dione | 64726-42-7

• 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: (5R)-5-(1,3-benzodioxol-5-ylmethyl)-5-methylimidazolidine-2,4-dione
• CAS: 64726-42-7
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.23
• InChiKey: GLRYEKZAKBJMNV-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

文献信息

• Process for preparing optically active hydantoins
  申请人：KANEGAFUCHI KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0175312A2

  公开（公告）日：1986-03-26

  A process for preparing optically active hydantoins having the general formula (II): wherein R' and R2, which are different from each other, are independently alkyl group aralkyl, group, aryl group, substituted alkyl group, substituted aralkyl group, or substituted aryl group, or R' and R2 form an asymmetric cyclic compound, characterized in that one configuration of racemic N-carbamoyl-a-amino acid having the general formula (I): wherein R' and R2 are as above, is enzymatically converted into the corresponding hydantoins. The present invention provides a process for an optical resolution with a high efficiency which can be used for the synthesis of (S)-6-fluoro-spiro- [chroman-4,4' -imidazolidine] -2',5'-dione (USAN; Sorbinil), which is an optically active hydantoins attracting public attention as a preventive or a remedy for the particular chronic symptoms of diabetes such as cataract and neuropathy, and (S)-a-methyl- 3,4-di- hydroxyphenylalanine (L-methyldopa), which is an optically active amino acid widely used as antihypertensives. Further, the present invention provides a novel finding that N-carbamoyl-a-amino acid having no hydrogen atom on its a-carbon atom can be biochemically converted into hydantoins by an enzymatic cyclization reaction.

  一种具有通式(II)的光学活性海因的制备方法： 其中R'和R2互不相同，独立地为烷基、芳基、取代的烷基、取代的芳基或取代的芳基，或R'和R2形成不对称环状化合物，其特征在于具有通式(I)的外消旋N-氨基甲酰基-a-氨基酸的一种构型： 其中 R' 和 R2 如上，通过酶法转化为相应的海因。 本发明提供了一种高效光学分解工艺，可用于合成(S)-6-氟-螺-[色满-4,4' -咪唑烷] -2',5'-二酮（USAN；(S)-a-甲基-3,4-二羟基苯丙氨酸(L-甲基多巴)，它是一种光学活性海因，作为白内障和神经病变等糖尿病特殊慢性症状的预防或治疗药物而备受公众关注；(S)-a-甲基-3,4-二羟基苯丙氨酸(L-甲基多巴)，它是一种光学活性氨基酸，被广泛用作抗高血压药物。此外，本发明还提供了一项新发现，即碳原子上没有氢原子的 N-氨基甲酰基-a-氨基酸可通过酶环化反应生化转化为 hydantoins。
• US4812406A
  申请人：——

  公开号：US4812406A

  公开（公告）日：1989-03-14