2,5,6-Trifluoro-4-methoxy-nicotinic acid benzyl ester | 858860-03-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5,6-Trifluoro-4-methoxy-nicotinic acid benzyl ester
• CAS: 858860-03-4
• 化学式: C₁₄H₁₀F₃NO₃
• 分子量: 297.234
• InChiKey: LXAHJZUYVBJVCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  48.42
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,5,6-Trifluoro-4-methoxy-nicotinic acid benzyl ester 在 palladium on activated charcoal 四氢呋喃 、 sodium hydroxide 、 草酰氯 、 氢气 、 乙酸酐 、 sodium hydride 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 乙腈 、 magnesium chloride 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 6-Fluoro-5-methoxy-4-oxo-7-pyrrolidin-1-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial activity of 5-methoxy- and 5-hydroxy-6-fluoro-1,8-naphthyridone-3-carboxylic acid derivatives

  摘要：

  A series of 5-methoxy- and 5-hydroxy-6-fluoro-1,8-naphthyridone-3-carboxylic acid derivatives were prepared and evaluated for cell-free bacterial protein synthesis inhibition and whole cell antibacterial activity. When compared to the analogous 5-hydrogen compounds, the presence of the 5-OH group negatively affects biochemical potency. However, a tolerance of the 5-methoxy group is indicated. Only moderate whole cell antibacterial activity is seen, but this could be due to poor cellular penetration, Because only a few 7-position variants were made for this study, further investigation into this novel series combining a broader range of 7-amino derivatives with these 5-position modifications is warranted. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.007
• 作为产物：
  描述：

  3-氯-2,4,5,6-四氟吡啶 在 palladium on activated charcoal 正丁基锂 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， -78.0~20.0 ℃ 、303.98 kPa 条件下， 反应 46.0h， 生成 2,5,6-Trifluoro-4-methoxy-nicotinic acid benzyl ester
  参考文献：
  名称：

  Synthesis and antibacterial activity of 5-methoxy- and 5-hydroxy-6-fluoro-1,8-naphthyridone-3-carboxylic acid derivatives

  摘要：

  A series of 5-methoxy- and 5-hydroxy-6-fluoro-1,8-naphthyridone-3-carboxylic acid derivatives were prepared and evaluated for cell-free bacterial protein synthesis inhibition and whole cell antibacterial activity. When compared to the analogous 5-hydrogen compounds, the presence of the 5-OH group negatively affects biochemical potency. However, a tolerance of the 5-methoxy group is indicated. Only moderate whole cell antibacterial activity is seen, but this could be due to poor cellular penetration, Because only a few 7-position variants were made for this study, further investigation into this novel series combining a broader range of 7-amino derivatives with these 5-position modifications is warranted. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.007