(2S)-benzyl 4--2-<<(1,1-dimethylethoxy)carbonyl>amino>butanoate | 158534-33-9

• 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)-benzyl 4--2-<<(1,1-dimethylethoxy)carbonyl>amino>butanoate
• 英文别名: (2S)-benzyl 4-[N-(benzyloxy)-N'-(ethoxycarbonyl)ureido]-2-{[(1,1-dimethylethoxy)carbonyl]amino}butanoate；benzyl (2S)-4-[ethoxycarbonylcarbamoyl(phenylmethoxy)amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 158534-33-9
• 化学式: C₂₇H₃₅N₃O₈
• 分子量: 529.59
• InChiKey: LUPFSPOAAPQDMT-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S)-benzyl 4--2-<<(1,1-dimethylethoxy)carbonyl>amino>butanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以85%的产率得到(2S)-<<(1,1-dimethylethoxy)carbonyl>amino>-4-butanoic 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：

  (2S)-2-[[(1,1-二甲基乙氧基)羰基]氨基]-4-氧代-丁酸苯甲酯 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 48.02h， 生成 (2S)-benzyl 4--2-<<(1,1-dimethylethoxy)carbonyl>amino>butanoate
  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.