(2S,5S,6S)-6-(4-Bromo-phenyl)-1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-5-methyl-piperidine-2-carboxylic acid methyl ester | 916914-48-2

• 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: (2S,5S,6S)-6-(4-Bromo-phenyl)-1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-5-methyl-piperidine-2-carboxylic acid methyl ester
• CAS: 916914-48-2
• 化学式: C₂₈H₃₅BrN₂O₅
• 分子量: 559.5
• InChiKey: LZWZYQRVSBIRFR-IMNFJDCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  84.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,5S,6S)-6-(4-Bromo-phenyl)-1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-5-methyl-piperidine-2-carboxylic acid methyl ester 在 2,6-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 Amberlyst A₂₆ hydroxide resin 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 10.25h， 生成 (2S,5S,6S)-6-(4-bromophenyl)-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
• 作为产物：
  描述：

  (2S,5S,6S)-6-(4-Bromo-phenyl)-5-methyl-1-(2,2,2-trifluoro-acetyl)-piperidine-2-carboxylic acid methyl ester 、 BOC-L-苯丙氨酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 反应 24.0h， 以25%的产率得到(2S,5S,6S)-6-(4-Bromo-phenyl)-1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-5-methyl-piperidine-2-carboxylic acid methyl ester
  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