(S)-Methyl 5-(1'-hydroxyethyl)-nicotinate

• 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)-Methyl 5-(1'-hydroxyethyl)-nicotinate
• 英文别名: methyl 5-[(1S)-1-hydroxyethyl]pyridine-3-carboxylate
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: WVNTUMMLZVFENY-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-乙酰基烟酸甲酯 在 ammonium dihydrogen phosphate 、 葡萄糖 、 magnesium sulfate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (S)-Methyl 5-(1'-hydroxyethyl)-nicotinate 、 (R)-Methyl 5-(1'-hydroxyethyl)-nicotinate
  参考文献：
  名称：

  Total syntheses and antimicrobial activities of pyridine alkaloids from Rubiaceae

  摘要：

  Pyridine alkaloids from Rubiaceae were prepared by palladium-catalyzed cross-coupling reactions of methyl 5-bromonicotinate (6) with various organometallic reagents. Baker's yeast reduction of the ketone 8 gave the levorotatory alcohol (S)-1. On this basis, the naturally occuring alcohol(+)-1 was assigned to be (R)-configurated. The alkaloids 1 and 4 show weak antimicrobial activities.

  DOI：

  10.1007/bf00807174

文献信息

• Total syntheses and antimicrobial activities of pyridine alkaloids from Rubiaceae
  作者：F. Bracher、T. Papke

  DOI：10.1007/bf00807174

  日期：——

  Pyridine alkaloids from Rubiaceae were prepared by palladium-catalyzed cross-coupling reactions of methyl 5-bromonicotinate (6) with various organometallic reagents. Baker's yeast reduction of the ketone 8 gave the levorotatory alcohol (S)-1. On this basis, the naturally occuring alcohol(+)-1 was assigned to be (R)-configurated. The alkaloids 1 and 4 show weak antimicrobial activities.