(2S)-methyl 4(R,S)-<(O-benzylhydroxy)amino>-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine-2-carboxylate

• 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: (2S)-methyl 4(R,S)-<(O-benzylhydroxy)amino>-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine-2-carboxylate
• 英文别名: 1-O-tert-butyl 2-O-methyl (2S)-4-(phenylmethoxyamino)pyrrolidine-1,2-dicarboxylate
• 化学式: C₁₈H₂₆N₂O₅
• 分子量: 350.415
• InChiKey: XMVAXPKPYWJFLQ-LOACHALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-methyl 4(R,S)-<(O-benzylhydroxy)amino>-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine-2-carboxylate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.52h， 生成 (2S,4S)-1-<(1,1-dimethylethoxy)carbonyl>-4-<2'-(3',5'-dioxo-1',2',4'-oxadiazolidinyl)>pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of Oxadiazolidinedione Derivatives as Quisqualic Acid Analogs and Their Evaluation at a Quisqualate-Sensitized Site in the Rat Hippocampus

  摘要：

  The ability of quisqualic acid (1) to sensitize neurons to depolarization by omega-phosphono alpha-amino acid analogues of excitatory amino acids is a highly specific phenomenon and is termed the QUIS. effect. In an attempt to elucidate the structure-activity relationships for this sensitization, analogues 2-6 of quisqualic acid have been synthesized. Compounds 4, 5, and 6 showed no quisqualate sensitization with respect to L-2-amino-6-phosphonohexanoic acid (L-AP6), while compounds 2 and 3 were 1/10 and 1/1000, respectively, as active as quisqualic acid in sensitizing neurons toward L-AP6.

  DOI：

  10.1021/jm00049a013
• 作为产物：
  描述：

  O-苄基羟胺 、 BOC-4-氧代-L-脯氨酸甲酯 在 盐酸 、 4 A molecular sieve 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 生成 (2S)-methyl 4(R,S)-<(O-benzylhydroxy)amino>-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Synthesis of Oxadiazolidinedione Derivatives as Quisqualic Acid Analogs and Their Evaluation at a Quisqualate-Sensitized Site in the Rat Hippocampus

  摘要：

  The ability of quisqualic acid (1) to sensitize neurons to depolarization by omega-phosphono alpha-amino acid analogues of excitatory amino acids is a highly specific phenomenon and is termed the QUIS. effect. In an attempt to elucidate the structure-activity relationships for this sensitization, analogues 2-6 of quisqualic acid have been synthesized. Compounds 4, 5, and 6 showed no quisqualate sensitization with respect to L-2-amino-6-phosphonohexanoic acid (L-AP6), while compounds 2 and 3 were 1/10 and 1/1000, respectively, as active as quisqualic acid in sensitizing neurons toward L-AP6.

  DOI：

  10.1021/jm00049a013

文献信息

• Synthesis of Oxadiazolidinedione Derivatives as Quisqualic Acid Analogs and Their Evaluation at a Quisqualate-Sensitized Site in the Rat Hippocampus
  作者：Shankar Venkatraman、Robert J. Roon、Marvin K. Schulte、James F. Koerner、Rodney L. Johnson

  DOI：10.1021/jm00049a013

  日期：1994.11

  The ability of quisqualic acid (1) to sensitize neurons to depolarization by omega-phosphono alpha-amino acid analogues of excitatory amino acids is a highly specific phenomenon and is termed the QUIS. effect. In an attempt to elucidate the structure-activity relationships for this sensitization, analogues 2-6 of quisqualic acid have been synthesized. Compounds 4, 5, and 6 showed no quisqualate sensitization with respect to L-2-amino-6-phosphonohexanoic acid (L-AP6), while compounds 2 and 3 were 1/10 and 1/1000, respectively, as active as quisqualic acid in sensitizing neurons toward L-AP6.