3-[4-(methylthio)phenyl]-2-oxo-5-methyloxazolidine

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-[4-(methylthio)phenyl]-2-oxo-5-methyloxazolidine
• 英文别名: 5-Methyl-3-(4-methylsulfanylphenyl)-1,3-oxazolidin-2-one
• 化学式: C₁₁H₁₃NO₂S
• 分子量: 223.296
• InChiKey: UJQVVEDVOKWZFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[4-(methylthio)phenyl]-2-oxo-5-methyloxazolidine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到3-[4-(methylsulfonyl)phenyl]-2-oxo-5-methyloxazolidine
  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：

  tert-butyl (4-(methylthio)phenyl)carbamate 在 Carreira’s cobalt catalyst 、 1,1,3,3-四甲基二硅氧烷 、 sodium hydride 、 1-氟-2,4,6-三甲基吡啶三氟甲烷磺酸盐 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 22.5h， 生成 3-[4-(methylthio)phenyl]-2-oxo-5-methyloxazolidine
  参考文献：
  名称：

  通过氢原子转移和自由基-极性交换催化合成环状氨基甲酸酯和尿素。

  摘要：

  在过渡金属氢原子转移和自由基-极性交叉概念的指导下，我们开发了一种功能强大且可扩展的方法，用于合成在生物活性化合物结构中发现的环状氨基甲酸酯和脲。该方法不仅提供普通的五元环，而且提供六至八元环的产品。反应通过烷基钴（IV）中间体的分子内置换和2,4,6-可力丁的脱烷基反应进行；这些步骤的活化能通过DFT计算。

  DOI：

  10.1021/acs.orglett.0c01872

文献信息

• Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group
  作者：Walter A. Gregory、David R. Brittelli、C. L. J. Wang、Mark A. Wuonola、Ronald J. McRipley、David C. Eustice、Virginia S. Eberly、Andrew M. Slee、Martin Forbes、P. T. Bartholomew

  DOI：10.1021/jm00128a003

  日期：1989.8

  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.
• Catalytic Dealkylative Synthesis of Cyclic Carbamates and Ureas via Hydrogen Atom Transfer and Radical-Polar Crossover
  作者：Takuya Nagai、Nao Mimata、Yoshihiro Terada、Chikayoshi Sebe、Hiroki Shigehisa

  DOI：10.1021/acs.orglett.0c01872

  日期：2020.7.17

  Guided by the transition-metal hydrogen atom transfer and radical-polar crossover concepts, we developed a functional-group-tolerant and scalable method for the synthesis of cyclic carbamates and ureas, which are found in the structures of bioactive compounds. This method provides not only a common five-membered ring but also six-to-eight-membered ring products. The reaction proceeds through the intramolecular

  在过渡金属氢原子转移和自由基-极性交叉概念的指导下，我们开发了一种功能强大且可扩展的方法，用于合成在生物活性化合物结构中发现的环状氨基甲酸酯和脲。该方法不仅提供普通的五元环，而且提供六至八元环的产品。反应通过烷基钴（IV）中间体的分子内置换和2,4,6-可力丁的脱烷基反应进行；这些步骤的活化能通过DFT计算。