3-<(4-acetylphenyl)amino>-1,2-propanediol | 64590-54-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-<(4-acetylphenyl)amino>-1,2-propanediol
• 英文别名: 3-[(4-acetylphenyl)amino]-1,2-propanediol；1-[4-(2,3-dihydroxypropylamino)phenyl]ethanone
• CAS: 64590-54-1
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: UTEMKVWXXWVYJA-UHFFFAOYSA-N

物化性质

• 沸点：
  449.4±40.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-<(4-acetylphenyl)amino>-1,2-propanediol 在 吡啶 、 sodium methylate 作用下， 以 甲苯 为溶剂， 生成 <3-(4-acetylphenyl)-2-oxo-5-oxazolidinyl>methyl methanesulfonate
  参考文献：
  名称：

  Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group

  摘要：

  The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other "B" functionalities by using SN2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different "B" groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 micrograms/mL for the most active compounds described.

  DOI：

  10.1021/jm00128a003
• 作为产物：
  描述：

  缩水甘油 、 4-氨基苯乙酮 以 乙醇 为溶剂， 反应 26.0h， 以56%的产率得到3-<(4-acetylphenyl)amino>-1,2-propanediol
  参考文献：
  名称：

  Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group

  摘要：

  The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other "B" functionalities by using SN2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different "B" groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 micrograms/mL for the most active compounds described.

  DOI：

  10.1021/jm00128a003