(R)-<3-<4-(methylthio)phenyl>-2-oxo-5-oxazolidinyl>methyl butyrate | 121373-23-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R)-<3-<4-(methylthio)phenyl>-2-oxo-5-oxazolidinyl>methyl butyrate
• 英文别名: (R)-{3-[4-(methylthio)phenyl]-2-oxo-5-oxazolidinyl}methyl butyrate
• CAS: 121373-23-7
• 化学式: C₁₅H₁₉NO₄S
• 分子量: 309.386
• InChiKey: WXFOMHMETXVJSL-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-<3-<4-(methylthio)phenyl>-2-oxo-5-oxazolidinyl>methyl butyrate 在 吡啶 、 1,3-丙二硫醇 、 sodium hydroxide 、 sodium azide 、 18-冠醚-6 、 sodium methylate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 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：

  异氰酸- 4(甲硫基)苯酯 、 (R)-(-)-丁酸缩水甘油酯 在 三正丁基氧化磷 、 lithium bromide 作用下， 以 xylene 为溶剂， 反应 2.0h， 以100%的产率得到(R)-<3-<4-(methylthio)phenyl>-2-oxo-5-oxazolidinyl>methyl butyrate
  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