glycidyl 2,2,2-trifluoroethoxysulfonylcarbamate | 233756-82-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: glycidyl 2,2,2-trifluoroethoxysulfonylcarbamate
• 英文别名: oxiran-2-ylmethyl N-(2,2,2-trifluoroethoxysulfonyl)carbamate
• CAS: 233756-82-6
• 化学式: C₆H₈F₃NO₆S
• 分子量: 279.194
• InChiKey: FJJHOBXWWOMHLF-UHFFFAOYSA-N

物化性质

• 密度：
  1.633±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  glycidyl 2,2,2-trifluoroethoxysulfonylcarbamate 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以48%的产率得到4-hydroxymethyl-3-(2,2,2-trifluoroethoxysulfonyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Preparation and Antimicrobial Studies of Acyclic Sulfamates.

  摘要：

  A series of acyclic sulfamates have been prepared and tested for antimicrobial activity. Thus, the oxysulfonyl isocyanates, ROSO2NCO (1a, R = 4-methoxyphenyl; 1b, R = phenyl; 1c, R = 4-chlorophenyl and 1d, R = 2,2,2-trifluoroethyl) have been prepared in 76-91% yield from chlorosulfonyl isocyanate. Treatment of lad with glycidol gave the glycidyl carbamates 2a-d. Internal cyclisation afforded the corresponding 3-hydroxymethyl-2-oxazolidinones 3a d, which in turn were hydrolysed to give the free amino alcohols 4a-d. The yields were in the range 39-85%. A preliminary agar diffusion test of 2a-d, 3a d, 4a d indicated 2a-d and 3e to be possible antimicrobial agents. A more thorough analysis of these compounds revealed a minimum inhibition concentration (MIC) of 128 and 64 mg 1(-1) for glycidyl p-methoxyphenoxysulfonylcarbamate (2a) and glycidyl phenoxysulfonylcarbamate (2b) respectively, against Branhamella catarrhalis.

  DOI：

  10.3891/acta.chem.scand.53-0446
• 作为产物：
  描述：

  2,2,2-trifluoroethoxysulfonyl isocyanate 、 缩水甘油 以 氯苯 为溶剂， 以79%的产率得到glycidyl 2,2,2-trifluoroethoxysulfonylcarbamate
  参考文献：
  名称：

  Preparation and Antimicrobial Studies of Acyclic Sulfamates.

  摘要：

  A series of acyclic sulfamates have been prepared and tested for antimicrobial activity. Thus, the oxysulfonyl isocyanates, ROSO2NCO (1a, R = 4-methoxyphenyl; 1b, R = phenyl; 1c, R = 4-chlorophenyl and 1d, R = 2,2,2-trifluoroethyl) have been prepared in 76-91% yield from chlorosulfonyl isocyanate. Treatment of lad with glycidol gave the glycidyl carbamates 2a-d. Internal cyclisation afforded the corresponding 3-hydroxymethyl-2-oxazolidinones 3a d, which in turn were hydrolysed to give the free amino alcohols 4a-d. The yields were in the range 39-85%. A preliminary agar diffusion test of 2a-d, 3a d, 4a d indicated 2a-d and 3e to be possible antimicrobial agents. A more thorough analysis of these compounds revealed a minimum inhibition concentration (MIC) of 128 and 64 mg 1(-1) for glycidyl p-methoxyphenoxysulfonylcarbamate (2a) and glycidyl phenoxysulfonylcarbamate (2b) respectively, against Branhamella catarrhalis.

  DOI：

  10.3891/acta.chem.scand.53-0446

文献信息

• Preparation and Antimicrobial Studies of Acyclic Sulfamates.
  作者：Hanna S. H. Gautun、Tom Bergan、Per H. J. Carlsen、Mia Helkearo、Harri Lönnberg、Shi-Ping Yan、Geng-Lin Wang、Xin-Kan Yao、Hong-Gen Wang、J. -P. Tuchagues、Mattias Ögren

  DOI：10.3891/acta.chem.scand.53-0446

  日期：——

  A series of acyclic sulfamates have been prepared and tested for antimicrobial activity. Thus, the oxysulfonyl isocyanates, ROSO2NCO (1a, R = 4-methoxyphenyl; 1b, R = phenyl; 1c, R = 4-chlorophenyl and 1d, R = 2,2,2-trifluoroethyl) have been prepared in 76-91% yield from chlorosulfonyl isocyanate. Treatment of lad with glycidol gave the glycidyl carbamates 2a-d. Internal cyclisation afforded the corresponding 3-hydroxymethyl-2-oxazolidinones 3a d, which in turn were hydrolysed to give the free amino alcohols 4a-d. The yields were in the range 39-85%. A preliminary agar diffusion test of 2a-d, 3a d, 4a d indicated 2a-d and 3e to be possible antimicrobial agents. A more thorough analysis of these compounds revealed a minimum inhibition concentration (MIC) of 128 and 64 mg 1(-1) for glycidyl p-methoxyphenoxysulfonylcarbamate (2a) and glycidyl phenoxysulfonylcarbamate (2b) respectively, against Branhamella catarrhalis.