(+)-S-2-oxarolziracetam | 141694-96-4

• 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: (+)-S-2-oxarolziracetam
• 英文别名: (7aS)-1,6,7,7a-tetrahydropyrrolo[1,2-c][1,3]oxazole-3,5-dione
• CAS: 141694-96-4
• 化学式: C₆H₇NO₃
• 分子量: 141.126
• InChiKey: BCJBJKPQPSYMKW-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二氧化碳 、 (S)-(+)-5-羟甲基-2-吡咯烷酮对甲苯磺酸酯 在 氧气 、 高氯酸四乙基铵 作用下， 生成 (+)-S-2-oxarolziracetam
  参考文献：
  名称：

  Electrogenerated Superoxide-Activated Carbon Dioxide. A New Mild and Safe Approach to Organic Carbamates

  摘要：

  The electrochemical reduction of O-2 (E = -1.0 V vs SCE) in dipolar aprotic solvents in the presence of CO2 gave a carboxylating reagent (O-2(.-)/CO2) able to convert amines and different types of their derivatives into carbamates. Primary and secondary aliphatic and aromatic amines were converted into the corresponding ethyl carbamates by the addition of EtI to the carbamate anions generated in the first step of the reactions. The yields were dependent on the nucleophilicity of the nitrogen atom. beta-Bromoethyl- and propylamine gave 2-oxazolidinone and tetrahydro-1,3-oxazin-2-one in moderate yields. N-Acyl or N-(alkoxycarbonyl)alkylamines bearing a leaving group at the beta position of the alkyl substituent were converted into 3-substituted-2-oxazolidinones in high yields. By using chiral substrates, enantiopure 3-alkoxycarbonyl(or acyl)-4-substituted oxazolidin-2-ones (70-85% isolated yields) were obtained. This represents a new mild and safe route to these important auxiliaries for asymmetric synthesis. Some limitations of the process are also evidenced and accounted for.

  DOI：

  10.1021/jo970308h

文献信息

• Synthesis of 2-Oxa and 2-Aza Analogs of Pyrrolizidine-3,5-diones (Lukes-Sorm Dilactam)
  作者：Tatsuo Nagasaka、Rie Hakamada、Shin-ichi Kunii、Fumiko Hamaguchi

  DOI：10.3987/com-91-s56

  日期：——

  The synthesis of 2-oxa and 2-aza analogs of pyrrolizidine-3,5-dione (Lukes-Sorm dilactam), which has amnesia reversal activity, is reported. Optically active (+)-2-oxa and (+)-2-aza analogs [(+)-2 and (+)-3] and racemic 2-aza analog and its 1-methoxycarbonyl derivatives [(+)-3 and (+)-13 and -14] were prepared from (-)-S-pyroglutamic acid and succinimide, respectively.
• Electrogenerated Superoxide-Activated Carbon Dioxide. A New Mild and Safe Approach to Organic Carbamates
  作者：Maria Antonietta Casadei、Franco Micheletti Moracci、Giovanni Zappia、Achille Inesi、Leucio Rossi

  DOI：10.1021/jo970308h

  日期：1997.10.1

  The electrochemical reduction of O-2 (E = -1.0 V vs SCE) in dipolar aprotic solvents in the presence of CO2 gave a carboxylating reagent (O-2(.-)/CO2) able to convert amines and different types of their derivatives into carbamates. Primary and secondary aliphatic and aromatic amines were converted into the corresponding ethyl carbamates by the addition of EtI to the carbamate anions generated in the first step of the reactions. The yields were dependent on the nucleophilicity of the nitrogen atom. beta-Bromoethyl- and propylamine gave 2-oxazolidinone and tetrahydro-1,3-oxazin-2-one in moderate yields. N-Acyl or N-(alkoxycarbonyl)alkylamines bearing a leaving group at the beta position of the alkyl substituent were converted into 3-substituted-2-oxazolidinones in high yields. By using chiral substrates, enantiopure 3-alkoxycarbonyl(or acyl)-4-substituted oxazolidin-2-ones (70-85% isolated yields) were obtained. This represents a new mild and safe route to these important auxiliaries for asymmetric synthesis. Some limitations of the process are also evidenced and accounted for.