(3R,4S) 3,4-dihydroxy-N-methoxycarbonylmethyl-2-pyrrolidinone | 154261-67-3

• 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: (3R,4S) 3,4-dihydroxy-N-methoxycarbonylmethyl-2-pyrrolidinone
• 英文别名: methyl 2-[(3R,4S)-3,4-dihydroxy-2-oxopyrrolidin-1-yl]acetate
• CAS: 154261-67-3
• 化学式: C₇H₁₁NO₅
• 分子量: 189.168
• InChiKey: QHAHNFZEKDLYLJ-UJURSFKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S) 3,4-dihydroxy-N-methoxycarbonylmethyl-2-pyrrolidinone 在 氨 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以60%的产率得到(3R,4S) 3,4-dihydroxy-2-oxopyrrolidine-N-acetamide
  参考文献：
  名称：

  Synthesis of the 3-hydroxy oxiracetam enantiomers, potential nootropic drugs

  摘要：

  The enantioselective synthesis of the potentially nootropic compounds 3-6 is reported. Derivative 3 was obtained from the readily available L-tartaric acid, by reduction of the imide 8 prepared with methyl glycinate. The other derivatives 4-6 were obtained from the dihydroxylactam 11. Protection of one of the hydroxyl groups and a Mitsunobu reaction or triflate displacement of the other group produces the remaining stereoisomers. Aminoderivatives 25 and 27 were obtained by displacement with sodium azide and reduction.

  DOI：

  10.1016/s0957-4166(00)82227-2
• 作为产物：
  描述：

  (3R,4R) 3,4-diacetoxy-N-methoxycarbonylmethyl-2-pyrrolidinone 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以3.6 g的产率得到(3R,4S) 3,4-dihydroxy-N-methoxycarbonylmethyl-2-pyrrolidinone
  参考文献：
  名称：

  Synthesis of the 3-hydroxy oxiracetam enantiomers, potential nootropic drugs

  摘要：

  The enantioselective synthesis of the potentially nootropic compounds 3-6 is reported. Derivative 3 was obtained from the readily available L-tartaric acid, by reduction of the imide 8 prepared with methyl glycinate. The other derivatives 4-6 were obtained from the dihydroxylactam 11. Protection of one of the hydroxyl groups and a Mitsunobu reaction or triflate displacement of the other group produces the remaining stereoisomers. Aminoderivatives 25 and 27 were obtained by displacement with sodium azide and reduction.

  DOI：

  10.1016/s0957-4166(00)82227-2