(3R,4R,7R,8R,9aS,10aS)-4,8-Bis-[4-(3-methoxy-prop-1-ynyl)-phenyl]-3,7-dimethyl-octahydro-4a,8a-diaza-anthraquinone

• 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: (3R,4R,7R,8R,9aS,10aS)-4,8-Bis-[4-(3-methoxy-prop-1-ynyl)-phenyl]-3,7-dimethyl-octahydro-4a,8a-diaza-anthraquinone
• 英文别名: (3S,6R,7R,10S,13R,14R)-7,14-bis[4-(3-methoxyprop-1-ynyl)phenyl]-6,13-dimethyl-1,8-diazatricyclo[8.4.0.03,8]tetradecane-2,9-dione
• 化学式: C₃₄H₃₈N₂O₄
• 分子量: 538.687
• InChiKey: RWKHXLWNDKZCNK-OKJMWXCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 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,5R,6R)-6-(4-(3-methoxyprop-1-ynyl)phenyl)-5-methylpiperidine-2-carboxylic acid 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79%的产率得到(3R,4R,7R,8R,9aS,10aS)-4,8-Bis-[4-(3-methoxy-prop-1-ynyl)-phenyl]-3,7-dimethyl-octahydro-4a,8a-diaza-anthraquinone
  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).