N-丁基-N-(对甲苯基磺酰基)-乙酰胺 | 71173-14-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-丁基-N-(对甲苯基磺酰基)-乙酰胺
• 英文名称: N-butyl-N-tosylacetamide
• 英文别名: acetyl-butyl-(toluene-4-sulfonyl)-amine；Acetyl-butyl-(toluol-4-sulfonyl)-amin；N-Acetyl-N-butyl-p-toluolsulfonamid；Acetamide, N-butyl-N-(p-tolyl)-；N-butyl-N-(4-methylphenyl)sulfonylacetamide
• CAS: 71173-14-3
• 化学式: C₁₃H₁₉NO₃S
• 分子量: 269.365
• InChiKey: GIVRXFUIQHEBRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-丁基-N-(对甲苯基磺酰基)-乙酰胺 在 1,3-二甲基-2-苯基-2H-苯并咪唑 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以82%的产率得到N-丁基乙酰胺
  参考文献：
  名称：

  Photochemical Desulfonylation ofN-Tosyl Amides by 2-Phenyl-N,N′-­Dimethylbenzimidazoline (PDMBI)

  摘要：

  光诱导电子转移反应在N-托烷基酰胺和2-苯基-N,N′-二甲基苯并咪唑啉（PDMBI）之间提供了一种高效的去磺酰化N-托烷基酰胺的方法。

  DOI：

  10.1055/s-2005-872693
• 作为产物：
  描述：

  对甲苯磺酰氯 在 zinc oxide-nanoparticle 作用下， 反应 1.5h， 生成 N-丁基-N-(对甲苯基磺酰基)-乙酰胺
  参考文献：
  名称：

  ZnO and ZnO-nanoparticles: Efficient and reusable heterogeneous catalysts for one-pot synthesis of N-acylsulfonamides and sulfonate esters

  摘要：

  Commercially available and preparative ZnO nanoparticles are reported as efficient and reusable catalysts for the chemoselective synthesis of N-acylsulfonamides and sulfonate esters. A one-pot sequential sulfonylation and acylation of amines took place to afford the N-acylsulfonamides in excellent yields under solvent-free conditions. The ZnO catalyst can be reused for without significant loss of catalytic activity. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2011.09.010

文献信息

• Efficient<i>N</i>-acylation of sulfonamides using cesium salt of Wells–Dawson heteropolyacid as catalyst: Synthesis of new<i>N</i>-acyl sulfonamides and cyclic imides
  作者：Nesma Benali、Chafika Bougheloum、Sabrina Alioua、Robila Belghiche、Abdelrani Messalhi

  DOI：10.1080/00397911.2018.1535077

  日期：2018.12.17

  Abstract N-acylation of substituted sulfonamides with different anhydrides in the presence of Cesium salt of Wells–Dawson heteropolyacid (Cs5HP2W18O62) as an efficient and reusable catalyst was investigated for the first time. Cs5HP2W18O62 was used with a catalytic amount in water as a green solvent. At room temperature, a series of N-acylsulfonamides were synthesized, while under refluxing conditions

  摘要 首次研究了在 Wells-Dawson 杂多酸铯盐 (Cs5HP2W18O62) 存在下，取代磺酰胺与不同酸酐的 N-酰化反应，该催化剂是一种高效且可重复使用的催化剂。Cs5HP2W18O62 以催化量在水中用作绿色溶剂。在室温下合成了一系列N-酰基磺酰胺，在回流条件下得到了新的含有磺酰基的环状酰亚胺。原子经济性、高产率、易于后处理以及简单的催化剂回收和可重复使用是该过程的关键特征。图形摘要
• The Chemistry of the N-Alkyl-N-nitrosoamides. II. A New Method for the Deamination of Aliphatic Amines
  作者：Emil H. White

  DOI：10.1021/ja01627a064

  日期：1955.11
• 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.
• Photochemical Desulfonylation of<i>N</i>-Tosyl Amides by 2-Phenyl-<i>N</i>,<i>N</i>′-­Dimethylbenzimidazoline (PDMBI)
  作者：Zhong-Li Liu、Wei Yu、Qiang Liu、Zhengang Liu、Yu-Lu Zhou、Wei Zhang、Li Yang

  DOI：10.1055/s-2005-872693

  日期：——

  Photoinduced electron transfer reaction between N-tosyl amides and 2-phenyl-N,N′-dimethylbenzimidazoline (PDMBI) provides an efficient approach for the desulfonylation of N-tosyl amides.

  光诱导电子转移反应在N-托烷基酰胺和2-苯基-N,N′-二甲基苯并咪唑啉（PDMBI）之间提供了一种高效的去磺酰化N-托烷基酰胺的方法。
• ZnO and ZnO-nanoparticles: Efficient and reusable heterogeneous catalysts for one-pot synthesis of N-acylsulfonamides and sulfonate esters
  作者：Fatemeh Tamaddon、Mohammad Reza Sabeti、Abbas Ali Jafari、Farhang Tirgir、Elham Keshavarz

  DOI：10.1016/j.molcata.2011.09.010

  日期：2011.12

  Commercially available and preparative ZnO nanoparticles are reported as efficient and reusable catalysts for the chemoselective synthesis of N-acylsulfonamides and sulfonate esters. A one-pot sequential sulfonylation and acylation of amines took place to afford the N-acylsulfonamides in excellent yields under solvent-free conditions. The ZnO catalyst can be reused for without significant loss of catalytic activity. (C) 2011 Elsevier B.V. All rights reserved.

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