4-benzyloxy-1-prop-2-ynyl-2(1H)-pyridone | 870854-90-3

• 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: 4-benzyloxy-1-prop-2-ynyl-2(1H)-pyridone
• 英文别名: 4-Phenylmethoxy-1-prop-2-ynylpyridin-2-one
• CAS: 870854-90-3
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: RYMMYIKJVZTFPY-UHFFFAOYSA-N

物化性质

• 沸点：
  460.1±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-1-prop-2-ynyl-2(1H)-pyridone 、 氯代肟基乙酸乙酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以79%的产率得到5-(4-benzyloxy-2-oxo-2H-pyridin-1-ylmethyl)-isoxazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Design and synthesis of 2-pyridones as novel inhibitors of the Bacillus anthracis enoyl-ACP reductase

  摘要：

  Enoyl-ACP reductase (ENR), the product of the FabI gene, from Bacillus anthracis (BaENR) is responsible for catalyzing the final step of bacterial fatty acid biosynthesis. A number of novel 2-pyridone derivatives were synthesized and shown to be potent inhibitors of BaENR. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.004
• 作为产物：
  描述：

  4-苄氧基-2(1H)-吡啶酮 、 3-溴丙炔 在 potassium tert-butylate 、 四丁基碘化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以83%的产率得到4-benzyloxy-1-prop-2-ynyl-2(1H)-pyridone
  参考文献：
  名称：

  A practical procedure for the selective N-alkylation of 4-alkoxy-2-pyridones and its use in a sulfone-mediated synthesis of N-methyl-4-methoxy-2-pyridone

  摘要：

  It has been found that selective N-alkylation of 4-alkoxy-2-pyridones can be achieved under anhydrous, mild conditions with tetrabutylammonium iodide and potassium tert-butoxide being employed as the catalyst and the base, respectively. The procedure was applied to the preparation of 4-methoxy-l-methyl-2-pyridone, a valuable building block for heterocycle synthesis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.095

文献信息

• A practical procedure for the selective N-alkylation of 4-alkoxy-2-pyridones and its use in a sulfone-mediated synthesis of N-methyl-4-methoxy-2-pyridone
  作者：David Conreaux、Emmanuel Bossharth、Nuno Monteiro、Philippe Desbordes、Geneviève Balme

  DOI：10.1016/j.tetlet.2005.09.095

  日期：2005.11

  It has been found that selective N-alkylation of 4-alkoxy-2-pyridones can be achieved under anhydrous, mild conditions with tetrabutylammonium iodide and potassium tert-butoxide being employed as the catalyst and the base, respectively. The procedure was applied to the preparation of 4-methoxy-l-methyl-2-pyridone, a valuable building block for heterocycle synthesis. (c) 2005 Elsevier Ltd. All rights reserved.
• Design and synthesis of 2-pyridones as novel inhibitors of the Bacillus anthracis enoyl-ACP reductase
  作者：Suresh K. Tipparaju、Sipak Joyasawal、Sara Forrester、Debbie C. Mulhearn、Scott Pegan、Michael E. Johnson、Andrew D. Mesecar、Alan P. Kozikowski

  DOI：10.1016/j.bmcl.2008.05.004

  日期：2008.6

  Enoyl-ACP reductase (ENR), the product of the FabI gene, from Bacillus anthracis (BaENR) is responsible for catalyzing the final step of bacterial fatty acid biosynthesis. A number of novel 2-pyridone derivatives were synthesized and shown to be potent inhibitors of BaENR. (C) 2008 Elsevier Ltd. All rights reserved.