(2S,5S,6S)-6-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-5-methyl-piperidine-2-carboxylic acid methyl ester | 1026201-47-7

• 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-(3-Dimethylamino-prop-1-ynyl)-phenyl]-5-methyl-piperidine-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,5S,6S)-6-[4-[3-(dimethylamino)prop-1-ynyl]phenyl]-5-methylpiperidine-2-carboxylate
• CAS: 1026201-47-7
• 化学式: C₁₉H₂₆N₂O₂
• 分子量: 314.428
• InChiKey: LGDJGMQFFJMXGB-WBAXXEDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,5S,6S)-6-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-5-methyl-piperidine-2-carboxylic acid methyl ester 在 Amberlyst A₂₆ hydroxide resin 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 (2S,5S,6S)-6-(4-(3-(dimethylamino)prop-1-ynyl)phenyl)-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 在 四(三苯基膦)钯 sodium tetrahydroborate 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.67h， 生成 (2S,5S,6S)-6-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-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