(5S)-5-[(pyrrolidin-1-yl)carbonyl]pyrrolidin-2-one | 85187-28-6

• 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: (5S)-5-[(pyrrolidin-1-yl)carbonyl]pyrrolidin-2-one
• 英文别名: (S)-5-(pyrrolidine-1-carbonyl)-pyrrolidin-2-one；(S)-5-(Pyrrolidin-1-carbonyl)-pyrrolidin-2-on；(S)-1-[(5-oxo-2-pyrrolidinyl)carbonyl]pyrrolidine；(S)-1-((5-Oxo-2-pyrrolidinyl)carbonyl)pyrrolidine；(5S)-5-(pyrrolidine-1-carbonyl)pyrrolidin-2-one
• CAS: 85187-28-6
• 化学式: C₉H₁₄N₂O₂
• 分子量: 182.222
• InChiKey: IWMYEQSITOXBMZ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S)-5-[(pyrrolidin-1-yl)carbonyl]pyrrolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(S)-(pyrrolidinemethyl)pyrrolidine
  参考文献：
  名称：

  Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline

  摘要：

  Efficient syntheses of chiral vicinal diamines derived from (S)-oxo-proline and (S)-proline are described. The novel diastereomerically pure precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]-octan-4,8-dione 3 and its enantiomer are readily available by reaction of the inexpensive enantiomers of 5-oxo-proline with chloral. Compound 3 reacts with primary and secondary amines to afford the 5-oxo-prolylamides 4 in quantitative yield. In contrast, the (S)-proline-derived precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 6 gave (S)-N-formylprolylamides 9 and/or (S)-prolylamides 8 depending on the reaction conditions. Upon reduction with LiAlH4, amides 4 and 9 afforded the proline-derived (S)-2-(alkylaminomethyl)pyrrolidines 1 and (S)-N- methyl-2-(alkylaminomethyl)-pyrrolidines 5 in 70-90% yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00579-7
• 作为产物：
  描述：

  四氢吡咯 、 (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octane-4,8-dione 以 乙腈 为溶剂， 反应 0.17h， 以95%的产率得到(5S)-5-[(pyrrolidin-1-yl)carbonyl]pyrrolidin-2-one
  参考文献：
  名称：

  Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline

  摘要：

  Efficient syntheses of chiral vicinal diamines derived from (S)-oxo-proline and (S)-proline are described. The novel diastereomerically pure precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]-octan-4,8-dione 3 and its enantiomer are readily available by reaction of the inexpensive enantiomers of 5-oxo-proline with chloral. Compound 3 reacts with primary and secondary amines to afford the 5-oxo-prolylamides 4 in quantitative yield. In contrast, the (S)-proline-derived precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 6 gave (S)-N-formylprolylamides 9 and/or (S)-prolylamides 8 depending on the reaction conditions. Upon reduction with LiAlH4, amides 4 and 9 afforded the proline-derived (S)-2-(alkylaminomethyl)pyrrolidines 1 and (S)-N- methyl-2-(alkylaminomethyl)-pyrrolidines 5 in 70-90% yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00579-7

文献信息

• Combination therapy for glycaemic control
  申请人：Demuth Hans-Ulrich

  公开号：US20060287251A1

  公开（公告）日：2006-12-21

  The present invention relates to method of treatment, in particular to a method for the treatment of diabetes mellitus, especially non-insulin dependent diabetes mellitus (NIDDM) or Type 2 diabetes and conditions associated with diabetes mellitus the predi,betic state and/or obesity and to compositions for use in s ch method.

  本发明涉及治疗方法，特别是一种用于治疗糖尿病的方法，尤其是非胰岛素依赖性糖尿病（NIDDM）或2型糖尿病以及与糖尿病相关的糖尿病前期状态和/或肥胖症的条件，以及用于该种方法的组合物。
• Notes - Some N-Substituted-5-oxo-2-pyrrolidinecarboxamides
  作者：R. B. Angier、V. K. Smith

  DOI：10.1021/jo01118a623

  日期：1956.12.1
• COMBINATION THERAPY FOR GLYCAEMIC CONTROL
  申请人：Prosidion Limited

  公开号：EP1663200A2

  公开（公告）日：2006-06-07
• US5102882A
  申请人：——

  公开号：US5102882A

  公开（公告）日：1992-04-07
• [EN] COMBINATION THERAPY FOR GLYCAEMIC CONTROL<br/>[FR] THERAPIE COMBINEE DE REGULATION GLYCEMIQUE
  申请人：PROSIDION LTD

  公开号：WO2005020983A2

  公开（公告）日：2005-03-10

  The present invention relates to method of treatment, in particular to a method for the treatment of diabetes mellitus, especiall non-insulin dependent diabetes mellitus (NIDDM) or Type 2 diabetes and conditions associat d with diabetes mellitus the predi,tbetic state and/or obesity and to compositions for use in s ch method.