4-azidomethyl-7-methyl-coumarin-6-sulfonyl chloride | 1220529-07-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-azidomethyl-7-methyl-coumarin-6-sulfonyl chloride
• 英文别名: 4-(Azidomethyl)-7-methyl-2-oxochromene-6-sulfonyl chloride
• CAS: 1220529-07-6
• 化学式: C₁₁H₈ClN₃O₄S
• 分子量: 313.721
• InChiKey: MUCMUXCHCKRTAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-azidomethyl-7-methyl-coumarin-6-sulfonyl chloride 、 2,4-二氯苯胺 以 苯 为溶剂， 反应 4.0h， 以67%的产率得到4-azidomethyl-7-methyl-coumarin-6-sulfonic acid (2,4-dichloro-phenyl)-amide
  参考文献：
  名称：

  Synthesis and antimicrobial studies on novel sulfonamides containing 4-azidomethyl coumarin

  摘要：

  A series of new and novel coumarin-6-sulfonamides with a free C4-azidomethyl group have been synthesized as antimicrobials in three steps starting from 7-methyl-4-bromomethylcoumarin 1. The reaction of I with chlorosulfonic acid was found to yield the corresponding 6-sulfonylchloride 2, which when treated with sodium azide led to intermediate 3. The title sulfonamides 5a-y were obtained from the reaction of 3 with various aromatic amines 4 in refluxing benzene. The chemical structures of the compounds were elucidated by IR, NMR and LC-MS spectral data. All the synthesized compounds have been screened for their in vitro anti-bacterial and anti-fungal activities. Some of the Compounds have been found to be active against both bacterial species at a concentration of 1 mu g/mL. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.022
• 作为产物：
  描述：

  4-bromomethyl-7-methyl-coumarin-6-sulfonyl chloride 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 反应 10.0h， 以65%的产率得到4-azidomethyl-7-methyl-coumarin-6-sulfonyl chloride
  参考文献：
  名称：

  Synthesis and antimicrobial studies on novel sulfonamides containing 4-azidomethyl coumarin

  摘要：

  A series of new and novel coumarin-6-sulfonamides with a free C4-azidomethyl group have been synthesized as antimicrobials in three steps starting from 7-methyl-4-bromomethylcoumarin 1. The reaction of I with chlorosulfonic acid was found to yield the corresponding 6-sulfonylchloride 2, which when treated with sodium azide led to intermediate 3. The title sulfonamides 5a-y were obtained from the reaction of 3 with various aromatic amines 4 in refluxing benzene. The chemical structures of the compounds were elucidated by IR, NMR and LC-MS spectral data. All the synthesized compounds have been screened for their in vitro anti-bacterial and anti-fungal activities. Some of the Compounds have been found to be active against both bacterial species at a concentration of 1 mu g/mL. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.022