(3S,6S,7S,10S,13S,14S)-7,14-bis(3-methoxyphenyl)-6,13-dimethyl-1,8-diazatricyclo[8.4.0.03,8]tetradecane-2,9-dione

• 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: (3S,6S,7S,10S,13S,14S)-7,14-bis(3-methoxyphenyl)-6,13-dimethyl-1,8-diazatricyclo[8.4.0.03,8]tetradecane-2,9-dione
• 化学式: C₂₈H₃₄N₂O₄
• 分子量: 462.589
• InChiKey: RFWORGCGLLFXDL-SFYJKWEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S,5S,6S)-6-(3-methoxyphenyl)-5-methylpiperidine-2-carboxylic acid 、 N-甲基-L-缬氨酸 在 2,3,5-三甲基吡啶 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以39%的产率得到(3S,6S,7S,9aS)-6-(3-methoxyphenyl)-2,7-dimethyl-3-propan-2-yl-3,6,7,8,9,9a-hexahydropyrido[1,2-a]pyrazine-1,4-dione
  参考文献：
  名称：

  Convergent Synthesis of Complex Diketopiperazines Derived from Pipecolic Acid Scaffolds and Parallel Screening against GPCR Targets

  摘要：

  A convergent approach to highly functionalized diketopiperazines (DKPs) using enantioenriched pipecolic acids is described. Scandium triflate-catalyzed [4 + 2] aza-annulation was employed to produce stereochemically well-defined building blocks. A resin "catch and release" strategy was devised to convert annulation products to pipecolic acid monomers. Complex diketopiperazines were efficiently assembled utilizing one-pot cyclodimerization of pipecolic acids. Massively parallel screening of the complex DKPs against a panel of molecular targets identified novel ligands for a number of G-protein-coupled receptors (GPCRs).

  DOI：

  10.1021/jo061758p

文献信息

• Convergent Synthesis of Complex Diketopiperazines Derived from Pipecolic Acid Scaffolds and Parallel Screening against GPCR Targets
  作者：Sivaraman Dandapani、Ping Lan、Aaron B. Beeler、Scott Beischel、Athier Abbas、Bryan L. Roth、John A. Porco,、James S. Panek

  DOI：10.1021/jo061758p

  日期：2006.11.1

  A convergent approach to highly functionalized diketopiperazines (DKPs) using enantioenriched pipecolic acids is described. Scandium triflate-catalyzed [4 + 2] aza-annulation was employed to produce stereochemically well-defined building blocks. A resin "catch and release" strategy was devised to convert annulation products to pipecolic acid monomers. Complex diketopiperazines were efficiently assembled utilizing one-pot cyclodimerization of pipecolic acids. Massively parallel screening of the complex DKPs against a panel of molecular targets identified novel ligands for a number of G-protein-coupled receptors (GPCRs).