4-(Benzylamino)-3-chloro-5-hydroxyfuran-2(5H)-one | 400712-09-6

• 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: 4-(Benzylamino)-3-chloro-5-hydroxyfuran-2(5H)-one
• 英文别名: 3-(benzylamino)-4-chloro-2-hydroxy-2H-furan-5-one
• CAS: 400712-09-6
• 化学式: C₁₁H₁₀ClNO₃
• 分子量: 239.658
• InChiKey: HYCOPHHDXNJHKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二氯-5-羟基-5H-呋喃-2-酮 、 N-苄基甲酰胺 在 硫酸 作用下， 以 甲苯 为溶剂， 以17%的产率得到4-(Benzylamino)-3-chloro-5-hydroxyfuran-2(5H)-one
  参考文献：
  名称：

  Synthesis and antibacterial activities of 5-hydroxy-4-amino-2(5H)-furanones

  摘要：

  Starting from the mucohalogen acids 1a and b 5-hydroxy-2(5H)-furanones 2a-h have been prepared and tested. These novel 4-amino-5-hydroxy 2(5H)-furananones have shown a broad antibiotic activity against Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853 in the micromolar range. A one step synthesis from mucohalogen acids towards the antibacterials 2a-h was developed, in which the target was obtained from la and b under reflux in toluene in presence of a catalytic amount of sulfuric acid. The derivatives 2b and c displayed a MIC and MBC of 4/8 mug/ml, against Staphylococcus aureus with a selectivity towards the resistant strains. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.051

文献信息

• Synthesis and antibacterial activities of 5-hydroxy-4-amino-2(5H)-furanones
  作者：Eric Lattmann、Simon Dunn、Suwanna Niamsanit、Nison Sattayasai

  DOI：10.1016/j.bmcl.2004.12.051

  日期：2005.2

  Starting from the mucohalogen acids 1a and b 5-hydroxy-2(5H)-furanones 2a-h have been prepared and tested. These novel 4-amino-5-hydroxy 2(5H)-furananones have shown a broad antibiotic activity against Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853 in the micromolar range. A one step synthesis from mucohalogen acids towards the antibacterials 2a-h was developed, in which the target was obtained from la and b under reflux in toluene in presence of a catalytic amount of sulfuric acid. The derivatives 2b and c displayed a MIC and MBC of 4/8 mug/ml, against Staphylococcus aureus with a selectivity towards the resistant strains. (C) 2005 Elsevier Ltd. All rights reserved.