(2S,5S,6S)-6-(3-Bromo-phenyl)-5-methyl-1-(2,2,2-trifluoro-acetyl)-piperidine-2-carboxylic acid methyl ester | 916914-45-9

• 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-(3-Bromo-phenyl)-5-methyl-1-(2,2,2-trifluoro-acetyl)-piperidine-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,5S,6S)-6-(3-bromophenyl)-5-methyl-1-(2,2,2-trifluoroacetyl)piperidine-2-carboxylate
• CAS: 916914-45-9
• 化学式: C₁₆H₁₇BrF₃NO₃
• 分子量: 408.215
• InChiKey: ISOFZUNKAPFZBM-XDTLVQLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,5S,6S)-6-(3-Bromo-phenyl)-5-methyl-1-(2,2,2-trifluoro-acetyl)-piperidine-2-carboxylic acid methyl ester 在 sodium tetrahydroborate 、 copper(l) iodide 、 potassium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 15.0h， 生成 (2S,5S,6S)-5-Methyl-6-[3-(2-oxo-pyrrolidin-1-yl)-phenyl]-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
• 作为产物：
  描述：

  methyl (2S,5S,6S)-6-(3-bromophenyl)-1-(2,2,2-trifluoroacetyl)-1,2,5,6-tetrahydro-5-methylpyridine-2-carboxylate 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (2S,5S,6S)-6-(3-Bromo-phenyl)-5-methyl-1-(2,2,2-trifluoro-acetyl)-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