Z-L-Pro-D-Pro-OMe | 60433-82-1

• 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: Z-L-Pro-D-Pro-OMe
• 英文别名: benzyl (S)-2-((R)-2-(methoxycarbonyl)pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate；methyl (2R)-1-[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]pyrrolidine-2-carboxylate
• CAS: 60433-82-1
• 化学式: C₁₉H₂₄N₂O₅
• 分子量: 360.41
• InChiKey: KALWJAOLQCJRJQ-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-L-Pro-D-Pro-OMe 在 钯 氢气 作用下， 以 甲醇 为溶剂， 生成 methyl (2R)-1-[(2S)-pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Facile Synthesis of Cyclic Dipeptides and Detection of Racemization

  摘要：

  通过回流二肽甲酯的甲醇溶液，合成了几个高产率和高纯度的环状二肽。通过Fischer法、Nitecki法和当前的甲醇回流法准备的环状二肽，在产率和光学纯度方面进行了比较。甲醇回流法通常能得到良好的结果。高效液相色谱法有效地应用于检测外消旋化。

  DOI：

  10.1246/bcsj.56.568
• 作为产物：
  描述：

  D-脯氨酸 在 氯化亚砜 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 Z-L-Pro-D-Pro-OMe
  参考文献：
  名称：

  N-methyl-D-aspartate receptor modulators and methods of making and using same

  摘要：

  揭示了在调节NMDA受体活性方面具有增强效力的化合物。这些化合物可用于治疗疾病和疾病，如学习、认知活动和镇痛，特别是在缓解和/或减轻神经病痛方面。还披露了口服制剂和其他药学上可接受的化合物给药形式，包括静脉注射制剂。

  公开号：

  US09994614B2

文献信息

• Prolylprolinol-Catalyzed Asymmetric Michael Addition of Aliphatic Aldehydes to Nitroalkenes
  作者：Dengfu Lu、Yuefa Gong、Weizhou Wang

  DOI：10.1002/adsc.200900687

  日期：2010.3.8

  Several novel prolylprolinol catalysts have been designed and synthesized. This type of compound showed high catalytic efficiency on promoting the direct addition of unmodified aldehydes to nitroalkenes. Among the catalysts surveyed, the least bulky member (8d) exhibited the best performance on both efficiency and stereoselectivity, providing the products with up to 97% ee value with 1.5–5 mol% catalyst

  已经设计和合成了几种新型的脯氨酰脯氨醇催化剂。这种类型的化合物在促进未改性的醛直接添加到硝基烯烃方面显示出高催化效率。在所调查的催化剂中，最小体积的成员（8d）在效率和立体选择性方面均表现出最佳性能，在1.5-5 mol％的催化剂负载量下，提供的产品具有高达97％ee的ee值。此外，已经进行了过渡态的计算研究，以解释高非对映选择性和对映选择性。
• Chiral Organolithium Complexes: The Effect of Ligand Structure on the Enantioselective Deprotonation of Boc-Pyrrolidine
  作者：Donald J. Gallagher、Shengde Wu、Nikola A. Nikolic、Peter Beak

  DOI：10.1021/jo00130a014

  日期：1995.12

  The efficacies of a number of s-BuLi/chiral ligand complexes as reagents for the asymmetric deprotonation of Boc-pyrrolidine (1) to provide enantioenriched 2-lithio-Boc-pyrrolidine (2) have been evaluated by the conversion of 2 to 2-(trimethylsilyl)-Boc-pyrrolidine (3). The syntheses of new enantioenriched proline-based and bispidine ligands are described. The most effective newly examined ligands are the diproline-based diamino alcohol 20 and the alpha-methylbenzylamine-derived bispidine 35, which provided (S)-3 and (R)-3 with enantiomeric excesses of 72% and 75%, respectively. Use of the ligand (-)-isosparteine (28) resulted in lower conversions and enantioselectivities than (-)-sparteine (27). A rationale is proposed to explain the relative rates of the lithiation of 1 by s-BuLi/TMEDA, 27, or 28 complexes and the remarkable effectiveness of(-)-sparteine as the best chiral ligand examined to date.
• N-METHYL-D-ASPARTATE RECEPTOR MODULATORS AND METHODS OF MAKING AND USING SAME
  申请人：Naurex, Inc.

  公开号：US20170210779A1

  公开（公告）日：2017-07-27

  Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of diseases and disorders, such as learning, cognitive activities, and analgesia, particularly in alleviating and/or reducing neuropathic pain. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.
• US9994614B2
  申请人：——

  公开号：US9994614B2

  公开（公告）日：2018-06-12
• [EN] N-METHYL-D-ASPARTATE RECEPTOR MODULATORS AND METHODS OF MAKING AND USING SAME<br/>[FR] MODULATEURS DU RÉCEPTEUR DE N-MÉTHYL-D-ASPARTATE ET LEURS PROCÉDÉS D'ÉLABORATION ET D'UTILISATION
  申请人：NAUREX INC

  公开号：WO2016014982A1

  公开（公告）日：2016-01-28

  Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of diseases and disorders, such as learning, cognitive activities, and analgesia, particularly in alleviating and/or reducing neuropathic pain. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.