N-isobutanoyl-methanesulfonamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-isobutanoyl-methanesulfonamide
• 英文别名: 2-methyl-N-methylsulfonylpropanamide
• 化学式: C₅H₁₁NO₃S
• 分子量: 165.213
• InChiKey: IDAXQFBVXIUWCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲基磺酰胺 、 异丁酸酐 在 氯化亚砜 、 silica gel 作用下， 反应 0.15h， 以98%的产率得到N-isobutanoyl-methanesulfonamide
  参考文献：
  名称：

  在多相和无溶剂条件下，在二氧化硅 (SiO2-Cl) 存在下轻松合成 N-酰基磺酰胺

  摘要：

  摘要 在氯化硅存在下，磺酰胺与羧酸氯化物和酸酐一起转化为相应的 N-酰基磺酰胺。所有反应均在非均相和无溶剂条件下进行。该方法提供了良好至高产率和纯度的 N-酰基磺酰胺产品。

  DOI：

  10.1080/00397910701750185

文献信息

• Facile Synthesis of<i>N</i>‐Acylsulfonamide in the Presence of Silica Chloride (SiO₂‐Cl) both under Heterogeneous and Solvent‐Free Conditions
  作者：Ahmad Reza Massah、Ahmad Reza Momeni、Mina Dabagh、Hamid Aliyan、Hamid Javaherian Naghash

  DOI：10.1080/00397910701750185

  日期：2008.1

  Abstract Sulfonamides were converted to the corresponding N‐acyl sulfonamides with carboxylic acid chlorides and anhydrides in the presence of silica chloride. All reactions were performed in both heterogeneous and solvent‐free conditions. This method provides the N‐acyl sulfonamides products in good to high yield and purity.

  摘要 在氯化硅存在下，磺酰胺与羧酸氯化物和酸酐一起转化为相应的 N-酰基磺酰胺。所有反应均在非均相和无溶剂条件下进行。该方法提供了良好至高产率和纯度的 N-酰基磺酰胺产品。
• Synthesis, in vitro antibacterial and carbonic anhydrase II inhibitory activities of N-acylsulfonamides using silica sulfuric acid as an efficient catalyst under both solvent-free and heterogeneous conditions
  作者：Ahmad Reza Massah、Hadi Adibi、Reza Khodarahmi、Ramin Abiri、Mohammad Bagher Majnooni、Sherita Shahidi、Beheshteh Asadi、Masomeh Mehrabi、Mohammad Ali Zolfigol

  DOI：10.1016/j.bmc.2008.04.011

  日期：2008.5

  Silica sulfuric acid catalyzes efficiently the reaction of sulfonamides with both carboxylic acid anhydrides and chlorides under solvent-free and heterogeneous conditions. All the reactions were done at room temperature and the N-acylsulfonamides were obtained with high yields and purity via an easy work-up procedure. This method is attractive and is in a close agreement with green chemistry. These

  二氧化硅硫酸可在无溶剂和非均相条件下有效催化磺酰胺与羧酸酐和氯化物的反应。所有反应均在室温下进行，并且通过简单的后处理程序以高收率和纯度获得了N-酰基磺酰胺。该方法是有吸引力的，并且与绿色化学密切相关。还研究了这些化合物的抗菌活性，包括革兰氏阳性球菌和革兰氏阴性杆菌，以及碳酸酐酶II的抑制活性。
• HClO4-SiO2 and NaHSO4-SiO2: Two Efficient Heterogeneous Catalysts for Synthesis of N-Acylsulfonamides under Solvent-free Conditions
  作者：Liqiang Wu、Chunguang Yang、Chong Zhang、Liming Yang

  DOI：10.2174/157017809787893019

  日期：2009.4.1

  A simple and efficient synthesis of N-acylsulfonamides has been accomplished by the reaction of sulfonamides with anhydrides under solvent-free conditions in the presence of HClO4-SiO2 or NaHSO4-SiO2.

  已经通过在无溶剂条件下，使用HClO4-SiO2或NaHSO4-SiO2的存在下，将磺酰胺与酸酐反应，成功实现了一种简单高效的N-酰基磺酰胺合成。
• A novel and efficient solvent-free and heterogeneous method for the synthesis of primary, secondary and bis-N-acylsulfonamides using metal hydrogen sulfate catalysts
  作者：Ahmad Reza Massah、Beheshteh Asadi、Mahdieh Hoseinpour、Azadeh Molseghi、Roozbeh Javad Kalbasi、Hamid Javaherian Naghash

  DOI：10.1016/j.tet.2009.06.112

  日期：2009.9

  Some metal hydrogen sulfates were used as acid catalysts in the N-acylation of different sulfonamides using carboxylic acid chlorides and anhydrides as acylating agents under both heterogeneous and solvent-free conditions. Al(HSO4)(3) and Zr(HSO4)(4) were found to have the highest activity and catalyze the reactions efficiently to furnish the primary N-acyl sulfonamides (RCONHSO2R'), secondary N-acylsulfonamides (RCONR '' SO2R') and bis-N-acylsulfonamnides [RCO(SO2R')N-R ''-N(SO2R')COR] in good to high yield. The mild reaction conditions, inexpensive and low toxicity of catalysts and easy work-up procedure make this method attractive. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis, Characterization, and Antimicrobial Evaluation of Sulfonamides Containing <i>N</i>-Acyl Moieties Catalyzed by Bismuth(III) Salts Under Both Solvent and Solvent-Free Conditions
  作者：Hadi Adibi、Ahmad Reza Massah、Mohammad Bagher Majnooni、Sherita Shahidi、Maryam Afshar、Ramin Abiri、Hamid Javaherian Naghash

  DOI：10.1080/00397910903318732

  日期：2010.8.16

  Efficient N-acylation of sulfonamides with both readily available carboxylic acid chlorides and anhydrides has been carried out with catalysis by bismuth(III) salts including BiCl3 and Bi (OTf)3. The reactions proceed rapidly in both heterogeneous and solvent-free conditions and afforded the corresponding N-acylsulfonamides in good to excellent yields. The mild reaction conditions and low toxicity of bismuth salts make this procedure attractive and in close agreement with the goals of green chemistry. Some of the synthesized compounds were evaluated in vitro as antimicrobial agents against representative strains of Gram-positive (Staphylococcus aureus ATCC 25922, clinical strains of Staphylococcus aureus VISA and Enterococcus spp.) and Gram-negative bacteria (Pseudomonas aeruginosa ATCC 27853, clinical strains of Klebsiella pneumonia and Escherichia coli) and as antifungal agents against Candida albicans (clinically isolated) by both disc diffusion and minimal inhibition concentration (MIC) methods. All these bacteria and fungi studied were screened against some antibiotics to compare with our chemicals' zone diameters.