(2S,5R,6R)-6-(4-acetylaminophenyl)-5-methylpiperidine-2-carboxylic acid | 916914-63-1

• 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: (2S,5R,6R)-6-(4-acetylaminophenyl)-5-methylpiperidine-2-carboxylic acid
• 英文别名: (2S,5R,6R)-6-(4-acetamidophenyl)-5-methylpiperidine-2-carboxylic acid
• CAS: 916914-63-1
• 化学式: C₁₅H₂₀N₂O₃
• 分子量: 276.335
• InChiKey: ROKAEAVGHPIHCA-BIGNPOOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,5R,6R)-6-(4-acetylaminophenyl)-5-methylpiperidine-2-carboxylic acid 、 (1R,3S)-1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-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39%的产率得到N-[4-(8-methyl-6,11-dioxo-12-phenyl-5a,6,7,8,9,10,10a,11,12,13-decahydro-5H-6a,11a,13-triaza-indeno[1,2-b]anthracen-7-yl)-phenyl]-acetamide
  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
• 作为产物：
  描述：

  methyl (2S,5R,6R)-6-(4-bromophenyl)-5-methylpiperidine-2-carboxylate 在 copper(l) iodide 、 Amberlyst A₂₆ hydroxide resin 、 potassium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 15.0h， 生成 (2S,5R,6R)-6-(4-acetylaminophenyl)-5-methylpiperidine-2-carboxylic acid
  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).