(4S,5S)-4-acetoxy-5-hydroxy-N-methoxycarbonylmethyl-2-pyrrolidinone | 146235-28-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S,5S)-4-acetoxy-5-hydroxy-N-methoxycarbonylmethyl-2-pyrrolidinone
• CAS: 146235-28-1
• 化学式: C₉H₁₃NO₆
• 分子量: 231.205
• InChiKey: ZICMECCEEIDEFG-RCOVLWMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.36
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  93.14
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-acetoxy-5-hydroxy-N-methoxycarbonylmethyl-2-pyrrolidinone 在 三乙基硅烷 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 (4S)-4-acetoxy-N-methoxycarbonylmethyl-2-pyrrolidinone
  参考文献：
  名称：

  New enantioselective synthesis of 4-hydroxy-2-oxopyrrolidine-N-acetamide (oxiracetam) from malic acid

  摘要：

  The enantioselective synthesis of oxiracetam has been accomplished from readily available optically active D(+) and L(-) malic acids. The key step of the described method involves the selective reduction of a chiral cyclic diimide; in this way, both enantiomers of 4-hydroxy-2-oxopyrrolidine-N-acetamides were prepared.

  DOI：

  10.1016/0957-4166(92)80020-w
• 作为产物：
  描述：

  (3S)-3-acetoxy-N-methoxycarbonylmethylsuccinimide 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.17h， 以73%的产率得到(4S,5S)-4-acetoxy-5-hydroxy-N-methoxycarbonylmethyl-2-pyrrolidinone
  参考文献：
  名称：

  New enantioselective synthesis of 4-hydroxy-2-oxopyrrolidine-N-acetamide (oxiracetam) from malic acid

  摘要：

  The enantioselective synthesis of oxiracetam has been accomplished from readily available optically active D(+) and L(-) malic acids. The key step of the described method involves the selective reduction of a chiral cyclic diimide; in this way, both enantiomers of 4-hydroxy-2-oxopyrrolidine-N-acetamides were prepared.

  DOI：

  10.1016/0957-4166(92)80020-w

文献信息

• New enantioselective synthesis of 4-hydroxy-2-oxopyrrolidine-N-acetamide (oxiracetam) from malic acid
  作者：Jesús F. Almeida、Josefa Anaya、Nieves Martin、Manuel Grande、Joaquín R. Moran、Ma Cruz Caballero

  DOI：10.1016/0957-4166(92)80020-w

  日期：1992.11

  The enantioselective synthesis of oxiracetam has been accomplished from readily available optically active D(+) and L(-) malic acids. The key step of the described method involves the selective reduction of a chiral cyclic diimide; in this way, both enantiomers of 4-hydroxy-2-oxopyrrolidine-N-acetamides were prepared.