methyl (2S)-1-[(S)-2-amino-2-oxo-1-phenylethyl]pyrrolidine-2-carboxylate | 1397680-09-9

• 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: methyl (2S)-1-[(S)-2-amino-2-oxo-1-phenylethyl]pyrrolidine-2-carboxylate
• 英文别名: methyl (2S,1S)-1-(1-carbamoyl-1-phenylmethyl)pyrrolidine-2-carboxylate；(2S,αS)-1-(α-carbamoyl-α-phenylmethyl)-pyrrolidine-2-carboxylic acid methyl ester；methyl (2S)-1-[(1S)-2-amino-2-oxo-1-phenylethyl]pyrrolidine-2-carboxylate
• CAS: 1397680-09-9
• 化学式: C₁₄H₁₈N₂O₃
• 分子量: 262.309
• InChiKey: DWGNHWSZTNJQJN-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-1-[(S)-2-amino-2-oxo-1-phenylethyl]pyrrolidine-2-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以77%的产率得到(4S,8aS)-4-phenyl-perhydropyrrolo[1,2-a]pyrazine-1,3-dione
  参考文献：
  名称：

  Synthesis of bicyclic 2,6-diketopiperazines via a three-step sequence involving an Ugi five-center, four-component reaction

  摘要：

  A three-step sequence involving an Ugi five-center, four-component reaction (U-5C-4CR), amide N-detertbutylation and cyclocondensation has been developed for easy access to diverse bicyclic 2,6-diketopiperazine (2,6-DKP) derivatives. In the key step, aromatic aldehydes were successfully coupled with cyclic alpha-amino acids and isocyanides in the course of U-5C-4CR. Boron trifluoride-acetic acid complex was developed as a new N-detertbutylating agent effective at rt. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.064
• 作为产物：
  描述：

  (2S,αS)-1-(α-(1,1,3,3-tetramethylbutyl)-carbamoyl-α-phenylmethyl)-pyrrolidine-2-carboxylic acid methyl ester 在 boron trifluoride diacetate 作用下， 以81%的产率得到methyl (2S)-1-[(S)-2-amino-2-oxo-1-phenylethyl]pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Synthesis of bicyclic 2,6-diketopiperazines via a three-step sequence involving an Ugi five-center, four-component reaction

  摘要：

  A three-step sequence involving an Ugi five-center, four-component reaction (U-5C-4CR), amide N-detertbutylation and cyclocondensation has been developed for easy access to diverse bicyclic 2,6-diketopiperazine (2,6-DKP) derivatives. In the key step, aromatic aldehydes were successfully coupled with cyclic alpha-amino acids and isocyanides in the course of U-5C-4CR. Boron trifluoride-acetic acid complex was developed as a new N-detertbutylating agent effective at rt. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.064

文献信息

• Synthesis of New Perhydropyrrolo[1,2-a]pyrazine Derivatives and Their Evaluation in Animal Models of Epilepsy
  作者：Maciej Dawidowski、Wojciech Lewandowski、Jadwiga Turło

  DOI：10.3390/molecules191015955

  日期：——

  A series of novel stereochemically pure derivatives of the investigative broad-spectrum anticonvulsant ADD408003 was designed and synthesized. Five-center four-component (U-5C-4CR) and four-center three-component (U-4C-3CR) variants of Ugi reaction were used in the key step of the synthetic pathways. The compounds obtained were evaluated for the anticonvulsant activitiy in the maximal electroshock seizure (MES), subcutaneous Metrazole (scMET) and minimal clonic seizure (6 Hz) animal models of epilepsy. The efficacies of most derivatives in the 6 Hz model of pharmacoresistant partial seizures were markedly higher than in the ‘classical’ MES and scMET models. The most active compounds, (4R,8aR)-3a, and (4S,8aS)-6 displayed median effective doses (ED50) of 47.90 and 126.19 mg/kg, respectively, for the 6 Hz test.

  设计并合成了新型广谱抗惊厥药物ADD408003的一系列立体化学纯衍生物。在合成路径的关键步骤中，使用了五中心四组分（U-5C-4CR）和四中心三组分（U-4C-组分的Ugi反应）的变体。获得的化合物在最大电休克发作（MES）、皮下甲戊二氮（scMET）和最小阵挛发作（6 Hz）的癫痫动物模型中进行了抗惊厥活性评估。大部分衍生物在耐药性部分发作的6 Hz模型中的疗效明显高于传统的MES和scMET模型。最活性的化合物，(4R,8aR)-3a和(4S,8aS)-6在6 Hz测试中分别显示出中效剂量（ED50）为47.90和126.19 mg/kg。
• Asymmetric Strecker Reaction with Chiral Amines: a Catalyst-Free Protocol Using Acetone Cyanohydrin in Water
  作者：Matteo Pori、Paola Galletti、Roberto Soldati、Daria Giacomini

  DOI：10.1002/ejoc.201201533

  日期：2013.3

  The synthesis of a series of new chiral α-aminonitriles was achieved in a diastereoselective Strecker reaction in a one-pot procedure with aldehydes, enantiopure amines, and acetone cyanohydrin in water. Primary and secondary amines derived from L-α-amino acids were used as sources of chirality. The reactions proceeded efficiently without any catalyst at room temperature. The diastereoselectivity of

  一系列新的手性 α-氨基腈的合成是在非对映选择性 Strecker 反应中与醛、对映纯胺和丙酮氰醇在水中的单锅程序中合成的。源自 L-α-氨基酸的伯胺和仲胺用作手性来源。反应在室温下在没有任何催化剂的情况下有效进行。研究了该过程的非对映选择性和新手性 α-氨基腈的构型稳定性。报告了通过 NMR 分析鉴定不稳定中间体，并报告了不对称诱导的拟议机制和模型。据报道，脯氨酸衍生的手性 α-氨基腈化学转化为手性氨基二酸、氨基和酰胺。
• Synthesis of bicyclic 2,6-diketopiperazines via a three-step sequence involving an Ugi five-center, four-component reaction
  作者：Maciej Dawidowski、Franciszek Herold、Marcin Wilczek、Jadwiga Turło、Andrzej Chodkowski、Anna Gomółka、Jerzy Kleps

  DOI：10.1016/j.tet.2012.07.064

  日期：2012.9

  A three-step sequence involving an Ugi five-center, four-component reaction (U-5C-4CR), amide N-detertbutylation and cyclocondensation has been developed for easy access to diverse bicyclic 2,6-diketopiperazine (2,6-DKP) derivatives. In the key step, aromatic aldehydes were successfully coupled with cyclic alpha-amino acids and isocyanides in the course of U-5C-4CR. Boron trifluoride-acetic acid complex was developed as a new N-detertbutylating agent effective at rt. (C) 2012 Elsevier Ltd. All rights reserved.