(S)-3-<4-(methylthio)phenyl>-2-oxo-5-(aminomethyl)oxazolidine | 96800-70-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (S)-3-<4-(methylthio)phenyl>-2-oxo-5-(aminomethyl)oxazolidine
• 英文别名: (S)-3-[4-(methylthio)phenyl]-2-oxo-5-(aminomethyl)oxazolidine；(5S)-5-(aminomethyl)-3-(4-methylsulfanylphenyl)-1,3-oxazolidin-2-one
• CAS: 96800-70-3
• 化学式: C₁₁H₁₄N₂O₂S
• 分子量: 238.31
• InChiKey: ZYKDAALZWQUXMC-VIFPVBQESA-N

物化性质

• 沸点：
  394.3±25.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-3-<4-(methylthio)phenyl>-2-oxo-5-(aminomethyl)oxazolidine 在 sodium hydroxide 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 N-[3-(4-甲基亚磺酰苯基)-2-氧代-1,3-恶唑烷-5-基甲基]乙酰胺
  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：

  (R)-<3-<4-(methylthio)phenyl>-2-oxo-5-oxazolidinyl>methyl azide 生成 (S)-3-<4-(methylthio)phenyl>-2-oxo-5-(aminomethyl)oxazolidine
  参考文献：
  名称：

  Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents

  摘要：

  新型氨甲基氧噁唑啉基苯衍生物，包括硫醚、亚硫醚、磺酰和磺酰胺衍生物，如（l）-N-[3-[4-(甲基亚磺基)苯基]-2-氧噁唑啉-5-基甲基]乙酰胺，具有有用的抗菌活性。

  公开号：

  US04705799A1