5-(aminomethyl)-3-(4-acetylphenyl)-2-oxooxazolidine | 96800-71-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(aminomethyl)-3-(4-acetylphenyl)-2-oxooxazolidine
• 英文别名: (l)-3-(4-acetylphenyl)-5-(aminomethyl)-2-oxazolidinone；3-(4-Acetylphenyl)-5-(aminomethyl)-1,3-oxazolidin-2-one
• CAS: 96800-71-4
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: HAQLOXLAXNXSOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(aminomethyl)-3-(4-acetylphenyl)-2-oxooxazolidine 在 sodium hydroxide 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 4.0h， 生成 tert-butyl N-<3-(4-acetylphenyl)-2-hydroxypropyl>carbamate
  参考文献：
  名称：

  Seneci, Pierfausto; Caspani, Marco; Ripamonti, Franca, Journal of the Chemical Society. Perkin transactions I, 1994, # 16, p. 2345 - 2352

  摘要：

  DOI：
• 作为产物：
  描述：

  <3-(4-acetylphenyl)-2-oxo-5-oxazolidinyl>methyl azide 在 三甲氧基磷 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.5h， 以37%的产率得到5-(aminomethyl)-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

文献信息

• Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04705799A1

  公开（公告）日：1987-11-10

  Novel aminomethyl oxooxazolidinyl benzene derivatives, including the sulfides, sulfoxides, sulfones and sulfonamides, such as (l)-N-[3-[4-(methylsulfinyl)phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide, possess useful antibacterial activity.

  新型氨甲基氧噁唑啉基苯衍生物，包括硫化物、亚硫酸盐、磺酰化物和磺酰胺，例如（l）-N-[3-[4-(甲基亚磺酰基)苯基]-2-氧噁唑啉-5-基甲基]乙酰胺，具有有用的抗菌活性。
• GREGORY, WALTER A.
  作者：GREGORY, WALTER A.

  DOI：——

  日期：——
• US4705799A
  申请人：——

  公开号：US4705799A

  公开（公告）日：1987-11-10