(R)-<3-(4-acetylphenyl)-2-oxo-5-oxazolidinyl>methyl methanesulfonate | 121373-17-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-<3-(4-acetylphenyl)-2-oxo-5-oxazolidinyl>methyl methanesulfonate
• 英文别名: (R)-N-<3-(4-acetylphenyl)-2-oxo-5-oxazolidinylmethyl>methanesulfonate；[(5R)-3-(4-acetylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate
• CAS: 121373-17-9
• 化学式: C₁₃H₁₅NO₆S
• 分子量: 313.331
• InChiKey: KJHOTPWRGIXNDA-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.98
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-<3-(4-acetylphenyl)-2-oxo-5-oxazolidinyl>methyl methanesulfonate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以94%的产率得到(R)-5-(iodomethyl)-3-(4-acetylphenyl)-2-oxooxazolidine
  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-acetylphenyl)-2-oxo-5-oxazolidinyl>methyl butyrate 在 sodium methylate 甲醇 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (R)-<3-(4-acetylphenyl)-2-oxo-5-oxazolidinyl>methyl methanesulfonate
  参考文献：
  名称：

  新型抗菌剂dup 721的手性合成

  摘要：

  描述了由4-乙酰基异氰酸酯（）和（R）-丁酸缩水甘油酯（）合成DuP 721 [（S）-N- [3-（4-乙酰苯基）-2-氧代-5-恶唑烷基甲基]乙酰胺]的手性合成方法。。

  DOI：

  10.1016/0040-4020(89)80130-9

文献信息

• WANG, CHIA-LIN J.;GREGORY, WALTER A.;WUONOLA, MARK A., TETRAHEDRON , 45,(1989) N, C. 1323-1326
  作者：WANG, CHIA-LIN J.、GREGORY, WALTER A.、WUONOLA, MARK A.

  DOI：——

  日期：——