4-oxo-1-phenyl-4-piperidin-1-ylbutan-2-one | 146380-08-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-oxo-1-phenyl-4-piperidin-1-ylbutan-2-one
• 英文别名: Piperidine, 1-(1,3-dioxo-4-phenylbutyl)-；4-phenyl-1-piperidin-1-ylbutane-1,3-dione
• CAS: 146380-08-7
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: UBYSXYRMDMUHGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-oxo-1-phenyl-4-piperidin-1-ylbutan-2-one 在 platinum(IV) oxide 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 40.0 ℃ 、620.53 kPa 条件下， 反应 96.0h， 生成 (2S)-2-{[(1R)-1-benzyl-3-oxo-3-piperidin-1-ylpropyl]amino}-2-phenylacetamide
  参考文献：
  名称：

  Highly Diastereoselective Heterogeneously Catalyzed Hydrogenation of Enamines for the Synthesis of Chiral β-Amino Acid Derivatives

  摘要：

  Pure (Z)-enamines readily prepared from beta-ketoesters and amides using (S)-phenylglycine amide were hydrogenated with very high diastereoselectivities (up to 200:1) using heterogeneous catalysis. Hydrogenolytic cleavage of the (S)-phenylglycine amide afforded the corresponding chiral beta-aminoesters and amides. The high geometrical purity of the (Z)-enamine and a simple activation procedure for the PtO2 catalyst are essential in achieving high selectivity.

  DOI：

  10.1021/ja038812t
• 作为产物：
  描述：

  哌啶 、 5-(1-hydroxy-2-phenylethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 以 苯 为溶剂， 反应 4.0h， 以89%的产率得到4-oxo-1-phenyl-4-piperidin-1-ylbutan-2-one
  参考文献：
  名称：

  Aminolysis of 5-Acyl-2,2-dimethyl-1,3-dioxane-4,6-diones (Acyl Meldrum's Acids) as a Versatile Method for the Synthesis of β-Oxo Carboxamides

  摘要：

  5-酰基-2,2-二甲基-1,3-二恶烷-4,6-二酮（酰基梅尔德鲁姆酸）与各种胺发生氨解反应，可以高产率得到相应的 ß-氧代羧酰胺。

  DOI：

  10.1055/s-1992-26338

文献信息

• [EN] PROCESS TO CHIRAL BETA-AMINO ACID DERIVATIVES<br/>[FR] PROCEDE DE SYNTHESE DE DERIVES D'ACIDES AMINES BETA CHIRAUX
  申请人：MERCK & CO INC

  公开号：WO2004085661A2

  公开（公告）日：2004-10-07

  The present invention relates to a process for the synthesis of chiral beta-amino acid derivatives and in particular to a process for the preparation of enantiomerically enriched beta-amino acid amide inhibitors of dipeptidyl peptidase-IV (DP-IV) which are useful for the treatment of Type 2 diabetes.

  本发明涉及一种手性β-氨基酸衍生物的合成过程，特别是一种制备对二肽基肽酶-IV（DP-IV）具有对映选择性的β-氨基酸酰胺抑制剂的方法，该抑制剂对2型糖尿病的治疗有用。
• Aminolysis of 5-Acyl-2,2-dimethyl-1,3-dioxane-4,6-diones (Acyl Meldrum's Acids) as a Versatile Method for the Synthesis of β-Oxo Carboxamides
  作者：Chwang Siek Pak、Heui Cheol Yang、Eun Bok Choi

  DOI：10.1055/s-1992-26338

  日期：——

  5-Acyl-2,2-dimethyl-1,3-dioxane-4,6-diones (acyl Meldrum's acids) underwent aminolysis with various amines to afford the corresponding ß-oxo carboxamides in high yields.

  5-酰基-2,2-二甲基-1,3-二恶烷-4,6-二酮（酰基梅尔德鲁姆酸）与各种胺发生氨解反应，可以高产率得到相应的 ß-氧代羧酰胺。
• Highly Diastereoselective Heterogeneously Catalyzed Hydrogenation of Enamines for the Synthesis of Chiral β-Amino Acid Derivatives
  作者：Norihiro Ikemoto、David M. Tellers、Spencer D. Dreher、Jinchu Liu、Angie Huang、Nelo R. Rivera、Eugenia Njolito、Yi Hsiao、J. Christopher McWilliams、J. Michael Williams、Joseph D. Armstrong、Yongkui Sun、David J. Mathre、Edward J. J. Grabowski、Richard D. Tillyer

  DOI：10.1021/ja038812t

  日期：2004.3.1

  Pure (Z)-enamines readily prepared from beta-ketoesters and amides using (S)-phenylglycine amide were hydrogenated with very high diastereoselectivities (up to 200:1) using heterogeneous catalysis. Hydrogenolytic cleavage of the (S)-phenylglycine amide afforded the corresponding chiral beta-aminoesters and amides. The high geometrical purity of the (Z)-enamine and a simple activation procedure for the PtO2 catalyst are essential in achieving high selectivity.