(4S)-4-(tert-Butoxymethyl)-1-methyl-2-oxoimidazolidine | 168292-65-7

• 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: (4S)-4-(tert-Butoxymethyl)-1-methyl-2-oxoimidazolidine
• 英文别名: (4S)-1-methyl-4-[(2-methylpropan-2-yl)oxymethyl]imidazolidin-2-one
• CAS: 168292-65-7
• 化学式: C₉H₁₈N₂O₂
• 分子量: 186.254
• InChiKey: GUDTZVDRZULNDO-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S)-4-(tert-Butoxymethyl)-1-methyl-2-oxoimidazolidine 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 14.83h， 生成 (4S)-3-<(2R)-2-(N-Benzylamino)propionyl>-4-(tert-butoxymethyl)-1-methyl-2-oxoimidazolidine
  参考文献：
  名称：

  Stereospecific Amination by Dynamic Kinetic Resolution Utilizing 2-Oxoimidazolidine-4-carboxylate as a Novel Chiral Auxiliary

  摘要：

  A novel type of stereospecific amination by dynamic kinetic resolution using (4S)-2-oxoimidazolidine-4-carboxylate (1) as a chiral auxiliary was developed. A reaction of a diastereomeric mixture of (4S)-3-[(2RS)-2-bromoacyl]-2-oxoimidazolidine-4-carboxylates 4 with an amine in the presence of a base in HMPA predominantly afforded (4S)-3-[(2R)-2-(alkylamino)acyl]-2-oxoimidazolidine-4-carboxylates (S,R)-7 in good yields. The reaction proceeded by stereospecific S(N)2 type amination incorporated with rapid interconversion between the substrates (S,S)-4 and (S,R)-4. Mechanistic study suggested that the unique stereoselectivity was induced through the interaction between an amine and the ester group of (S,S)-4 in the transition state. The chiral auxiliary was easily removed with alkoxide anion to afford the alpha-amino acid synthon in good yields.

  DOI：

  10.1021/jo00126a029
• 作为产物：
  描述：

  (4S)-3-<(Benzyloxy)carbonyl>-4-(tert-butoxymethyl)-1-methyl-2-oxoimidazolidine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以93%的产率得到(4S)-4-(tert-Butoxymethyl)-1-methyl-2-oxoimidazolidine
  参考文献：
  名称：

  Stereospecific Amination by Dynamic Kinetic Resolution Utilizing 2-Oxoimidazolidine-4-carboxylate as a Novel Chiral Auxiliary

  摘要：

  A novel type of stereospecific amination by dynamic kinetic resolution using (4S)-2-oxoimidazolidine-4-carboxylate (1) as a chiral auxiliary was developed. A reaction of a diastereomeric mixture of (4S)-3-[(2RS)-2-bromoacyl]-2-oxoimidazolidine-4-carboxylates 4 with an amine in the presence of a base in HMPA predominantly afforded (4S)-3-[(2R)-2-(alkylamino)acyl]-2-oxoimidazolidine-4-carboxylates (S,R)-7 in good yields. The reaction proceeded by stereospecific S(N)2 type amination incorporated with rapid interconversion between the substrates (S,S)-4 and (S,R)-4. Mechanistic study suggested that the unique stereoselectivity was induced through the interaction between an amine and the ester group of (S,S)-4 in the transition state. The chiral auxiliary was easily removed with alkoxide anion to afford the alpha-amino acid synthon in good yields.

  DOI：

  10.1021/jo00126a029