methyl (2S,5R,6R)-6-(2-bromophenyl)-1-(2,2,2-trifluoroacetyl)-1,2,5,6-tetrahydro-5-methylpyridine-2-carboxylate | 916914-99-3

• 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,5R,6R)-6-(2-bromophenyl)-1-(2,2,2-trifluoroacetyl)-1,2,5,6-tetrahydro-5-methylpyridine-2-carboxylate
• 英文别名: methyl (2R,3R,6S)-2-(2-bromophenyl)-3-methyl-1-(2,2,2-trifluoroacetyl)-3,6-dihydro-2H-pyridine-6-carboxylate
• CAS: 916914-99-3
• 化学式: C₁₆H₁₅BrF₃NO₃
• 分子量: 406.199
• InChiKey: XDURCVASDAYTQY-JIMOISOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  methyl (2S,5R,6R)-6-(2-bromophenyl)-1-(2,2,2-trifluoroacetyl)-1,2,5,6-tetrahydro-5-methylpyridine-2-carboxylate 在 偶氮二异丁腈 、 三(三甲基硅基)硅烷 作用下， 以 苯 为溶剂， 反应 4.0h， 以77%的产率得到(1R,3S,4S,6R)-N-(trifluoroacetyl)-3-(methoxycarbonyl)-6-methyl-7,8-benzo-2-azabicyclo[2.2.2]octane
  参考文献：
  名称：

  Skeletal Diversity through Radical Cyclization of Tetrahydropyridine Scaffolds

  摘要：

  Suitably functionalized tetrahydropyridines (methyl pipecolates) have been used as conformationally biased templates for radical cyclizations to access benzoisoquinuclidines and linearly fused indenopiperidines. Variation of skeletal types is determined by location of a radical-initiating element.

  DOI：

  10.1021/ol701722z
• 作为产物：
  描述：

  (E)-(2R,3R)-2-Amino-3-(dimethyl-phenyl-silanyl)-hex-4-enoic acid methyl ester 在 magnesium sulfate 、 三氟乙酸 、 三氟乙酸酐 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2S,5R,6R)-6-(2-bromophenyl)-1-(2,2,2-trifluoroacetyl)-1,2,5,6-tetrahydro-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

• Skeletal Diversity through Radical Cyclization of Tetrahydropyridine Scaffolds
  作者：Sivaraman Dandapani、Mihai Duduta、James S. Panek、John A. Porco

  DOI：10.1021/ol701722z

  日期：2007.9.1

  Suitably functionalized tetrahydropyridines (methyl pipecolates) have been used as conformationally biased templates for radical cyclizations to access benzoisoquinuclidines and linearly fused indenopiperidines. Variation of skeletal types is determined by location of a radical-initiating element.
• 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).