p-methoxyphenoxysulfonyl isocyanate | 14754-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: p-methoxyphenoxysulfonyl isocyanate
• 英文别名: (4-Methoxy-phenoxy)-sulfonylisocyanat；4-Methoxyphenyl sulfurisocyanatidate；(4-methoxyphenyl) N-(oxomethylidene)sulfamate
• CAS: 14754-47-3
• 化学式: C₈H₇NO₅S
• 分子量: 229.213
• InChiKey: BLGJTCYKECGAJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  96-99 °C(Press: 0.02 Torr)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  90.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-methoxyphenoxysulfonyl isocyanate 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 2-<(p-methoxyphenoxy)sulfonamido>-1,3-propanediol
  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：

  氯磺酰异氰酸酯 、 4-甲氧基苯酚 以 氯苯 为溶剂， 生成 p-methoxyphenoxysulfonyl isocyanate
  参考文献：
  名称：

  Lohaus,G., Chemische Berichte, 1972, vol. 105, p. 2791 - 2799

  摘要：

  DOI：

文献信息

• Acyl and sulfonyl isocyanates in .beta.-lactam synthesis
  作者：Anthony G. M. Barrett、Michael J. Betts、Ashley Fenwick

  DOI：10.1021/jo00202a006

  日期：1985.1
• BARRETT, A. G. M.;BETTS, M. J.;FENWICK, A., J. ORG. CHEM., 1985, 50, N 2, 169-175
  作者：BARRETT, A. G. M.、BETTS, M. J.、FENWICK, A.

  DOI：——

  日期：——
• Lohaus,G., Chemische Berichte, 1972, vol. 105, p. 2791 - 2799
  作者：Lohaus,G.

  DOI：——

  日期：——
• 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.