methyl (2S,5S,6S)-1-(2,2,2-trifluoroacetyl)-1,2,5,6-tetrahydro-6-(3-methoxyphenyl)-5-methylpyridine-2-carboxylate | 916914-43-7

• 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: methyl (2S,5S,6S)-1-(2,2,2-trifluoroacetyl)-1,2,5,6-tetrahydro-6-(3-methoxyphenyl)-5-methylpyridine-2-carboxylate
• 英文别名: methyl (2S,3S,6S)-2-(3-methoxyphenyl)-3-methyl-1-(2,2,2-trifluoroacetyl)-3,6-dihydro-2H-pyridine-6-carboxylate
• CAS: 916914-43-7
• 化学式: C₁₇H₁₈F₃NO₄
• 分子量: 357.329
• InChiKey: DMXFNSFKISAMSC-BPNCWPANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S,5S,6S)-1-(2,2,2-trifluoroacetyl)-1,2,5,6-tetrahydro-6-(3-methoxyphenyl)-5-methylpyridine-2-carboxylate 在 Amberlyst A₂₆ hydroxide resin 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以51%的产率得到(2S,5S,6S)-6-(3-methoxyphenyl)-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：

  2-amino-3-(dimethyl-phenyl-silanyl)-hex-4-enoic acid methyl ester 在 三氟乙酸酐 、 scandium tris(trifluoromethanesulfonate) 、 原甲酸三甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 methyl (2S,5S,6S)-1-(2,2,2-trifluoroacetyl)-1,2,5,6-tetrahydro-6-(3-methoxyphenyl)-5-methylpyridine-2-carboxylate
  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).