(R)-phenotropil | 949925-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-phenotropil
• 英文别名: 2-[(4R)-2-oxo-4-phenylpyrrolidin-1-yl]acetamide；(R)-phenylpiracetam；1-Pyrrolidineacetamide, 2-oxo-4-phenyl-, (4R)-
• CAS: 949925-07-9
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: LYONXVJRBWWGQO-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl [(4R)-2-oxo-4-phenylpyrrolidin-1-yl]acetate 在 氨 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以85%的产率得到(R)-phenotropil
  参考文献：
  名称：

  N-Carbamoylmethyl-4-(R)-Phenyl-2-Pyrrolidinone, Method of its Preparation and Pharmaceutical Use

  摘要：

  本发明涉及具有药理价值的N-氨甲基-4-苯基-2-吡咯酮（R-Carphedon）的R-对映体。其制备方法包括在强碱存在下将4（R）-苯基-2-吡咯酮与溴乙酸乙酯进行N-烷基化，并用氨处理中间体N-乙氧羰基甲基-4（R）-苯基-2-吡咯酮。

  公开号：

  US20100022784A1

文献信息

• Novel methods for the synthesis of 2-[(4R)-2-oxo-4-phenylpyrrolidin-1-yl]-acetamide ((R)-phenotropil)
  作者：M. Vorona、G. Veinberg、S. Vikainis、E. Kuznetsov、A. Lebedev、Yu. Ponomarev、A. Chernobrovijs、L. Zvejniece、M. Dambrova

  DOI：10.1007/s10593-012-1050-y

  日期：2012.8

  developed for the preparation of 2-[(4R)-2-oxo-4-phenylpyrrolidin-1-yl]acetamide ((R)-Phenotropil). In the first, n-butyl (3R)-4-amino-3-phenylbutyrate is alkylated with haloacetamide in DMF in the presence of potassium phosphate monohydrate, and the intermediate 4-carbamoylmethylamino-3-phenylbutyrate is subsequently cyclized by refluxing in toluene in the presence of potassium phosphate monohydrate

  已经开发出两种新颖的方法来制备2-[（（4 R）-2-氧--4-苯基吡咯烷-1-基]乙酰胺（（R -Phenotropil））。首先，在磷酸一水合物存在下，在DMF中用卤代乙酰胺将（3 R）-4-氨基-3-苯基丁酸正丁酯烷基化，然后通过在甲苯中回流将中间体4-氨基甲酰基甲基氨基-3-苯基丁酸环化。在磷酸钾一水合物和四丁基溴化铵存在下。第二，在相似条件下使用氯乙腈代替卤代乙酰胺。这两种方法都导致（[R）-Phenotropil在起始计算40-60％的产率Ñ丁基（3 - [R）-4-氨基-3-苯基丁酸酯。
• [EN] 4R,5S-ENANTIOMER OF 2-(5-METHYL-2-OXO-4-PHENYL-PYRROLIDIN-1-YL)-ACETAMIDE WITH NOOTROPIC ACTIVITY<br/>[FR] ENANTIOMÈRE 4R,5S DE 2-(5-MÉTHYL-2-OXO-4-PHÉNYL-PYRROLIDIN-1-YL)-ACÉTAMIDE AYANT UNE ACTIVITÉ NOOTROPIQUE
  申请人：GRINDEKS JSC

  公开号：WO2011054888A1

  公开（公告）日：2011-05-12

  The invention relates to the 5S,4R-enantiomer of 2-(5-methyl-2-oxo-4-phenyl- pyrrolidin-1-yl)-acetamide with cognition enhancing activity of high pharmacological value and to its preparation method which includes the synthesis of 5S-methyl-4R-phenylpyrrolidin-2-one, its N-alkylation with ethyl haloacetate and the treatment of intermediate ethyl 2-(5S-methyl-2-oxo-4R-phenyl-pyrrolidin-1-yl)-acetate with ammonia.

  本发明涉及具有高度药理价值的增强认知活性2-(5-甲基-2-氧代-4-苯基吡咯烷-1-基)乙酰胺的5S,4R-对映体及其制备方法，该方法包括合成5S-甲基-4R-苯基吡咯烷-2-酮，将其与乙基卤代乙酸酯进行N-烷基化，以及用氨处理中间体乙基2-(5S-甲基-2-氧代-4R-苯基吡咯烷-1-基)乙酸酯。
• N-Carbamoylmethyl-4-(R)-Phenyl-2-Pyrrolidinone, Method of its Preparation and Pharmaceutical Use
  申请人：Veinberg Grigory

  公开号：US20100022784A1

  公开（公告）日：2010-01-28

  The invention relates to the R-enantiomer of N-carbamoylmethyl-4-phenyl-2-pyrrolidinone (R-Carphedon) of pharmacological value. The method of its preparation includes the N-alkylation of 4(R)-phenyl-2-pyrrolidinone with ethyl bromoacetate in the presence of a strong base and the treatment of intermediate N-ethoxycarbonylmethyl-4(R)-phenyl-2-pyrrolidinone with ammonia.

  本发明涉及具有药理价值的N-氨甲基-4-苯基-2-吡咯酮（R-Carphedon）的R-对映体。其制备方法包括在强碱存在下将4（R）-苯基-2-吡咯酮与溴乙酸乙酯进行N-烷基化，并用氨处理中间体N-乙氧羰基甲基-4（R）-苯基-2-吡咯酮。
• 4R,5S-ENANTIOMER OF 2-(5-METHYL-2-OXO-4-PHENYL-PYRROLIDIN-1-YL)-ACETAMIDE WITH NOOTROPIC ACTIVITY
  申请人：Kalvins Ivars

  公开号：US20120215010A1

  公开（公告）日：2012-08-23

  The invention relates to the 5S,4R-enantiomer of 2-(5-methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide with cognition enhancing activity of high pharmacological value and to its preparation method which includes the synthesis of 5S-methyl-4R-phenylpyrrolidin-2-one, its N-alkylation with ethyl haloacetate and the treatment of intermediate ethyl 2-(5S-methyl-2-oxo-4R-phenyl-pyrrolidin-1-yl)-acetate with ammonia.

  本发明涉及一种具有高药理学价值的认知增强活性的2-(5-甲基-2-氧代-4-苯基-吡咯烷-1-基)-乙酰胺的5S,4R-对映体及其制备方法，其包括5S-甲基-4R-苯基吡咯烷-2-酮的合成，其与乙酰卤代酸酯的N-烷基化以及中间体乙酰基2-(5S-甲基-2-氧代-4R-苯基-吡咯烷-1-基)-乙酸酯的氨处理。
• N-Carbamoylmethy1-4-(R)-phenyl-2-pyrrolidinone, method of its preparation and pharmaceutical use
  申请人：Veinberg Grigory

  公开号：US09102615B2

  公开（公告）日：2015-08-11

  The invention relates to the R-enantiomer of N-carbamoylmethyl-4-phenyl-2-pyrrolidinone (R-Carphedon) of pharmacological value. The method of its preparation includes the N-alkylation of 4(R)-phenyl-2-pyrrolidinone with ethyl bromoacetate in the presence of a strong base and the treatment of intermediate N-ethoxycarbonylmethyl-4(R)-phenyl-2-pyrrolidinone with ammonia.

  本发明涉及药物价值的N-氨甲基-4-苯基-2-吡咯酮的R-对映体（R-Carphedon）。其制备方法包括在强碱存在下用乙溴乙酸酯对4（R）-苯基-2-吡咯酮进行N-烷基化，以及用氨处理中间体N-乙氧羰基甲基-4（R）-苯基-2-吡咯酮。