(S,S)-tert-butyl 4-hydroxy-2-methyl-6-propyl-3,4-dihydropyridine-1(2H)-carboxylate | 1321589-43-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S,S)-tert-butyl 4-hydroxy-2-methyl-6-propyl-3,4-dihydropyridine-1(2H)-carboxylate
• 英文别名: tert-butyl (2S,4S)-4-hydroxy-2-methyl-6-propyl-3,4-dihydro-2H-pyridine-1-carboxylate
• CAS: 1321589-43-8
• 化学式: C₁₄H₂₅NO₃
• 分子量: 255.357
• InChiKey: QHIJUUTYROEMMR-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-tert-butyl 2-methyl-4-oxo-6-propyl-3,4-dihydropyridine-1(2H)-carboxylate 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (S,R)-tert-butyl 4-hydroxy-2-methyl-6-propyl-3,4-dihydropyridine-1(2H)-carboxylate 、 (S,S)-tert-butyl 4-hydroxy-2-methyl-6-propyl-3,4-dihydropyridine-1(2H)-carboxylate
  参考文献：
  名称：

  Enantiospecific Synthesis of Pyridinones as Versatile Intermediates toward Asymmetric Piperidines

  摘要：

  The enantiospecific syntheses of pyridinones from amino acids via a gold-catalyzed strategy are reported. Excellent stereocontrol was observed during the cyclization. This approach provides a straightforward tool for further synthetic applications toward piperidines.

  DOI：

  10.1021/ol201698m

文献信息

• Enantiospecific Synthesis of Pyridinones as Versatile Intermediates toward Asymmetric Piperidines
  作者：Nicolas Gouault、Myriam Le Roch、Adèle Cheignon、Philippe Uriac、Michèle David

  DOI：10.1021/ol201698m

  日期：2011.8.19

  The enantiospecific syntheses of pyridinones from amino acids via a gold-catalyzed strategy are reported. Excellent stereocontrol was observed during the cyclization. This approach provides a straightforward tool for further synthetic applications toward piperidines.