N-tosylpentanamide | 144150-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-tosylpentanamide
• 英文别名: N-(4-methylphenyl)sulfonylpentanamide
• CAS: 144150-84-5
• 化学式: C₁₂H₁₇NO₃S
• 分子量: 255.338
• InChiKey: XHKOPSVYZOFHEV-UHFFFAOYSA-N

物化性质

• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-tosylpentanamide 在 四乙基溴化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以69%的产率得到戊酰胺
  参考文献：
  名称：

  Superoxide‐Mediated Regioselective Deblocking of the Tosyl Group from N‐Tosylcarboxamides

  摘要：

  DOI：

  10.1080/00397910600775416
• 作为产物：
  描述：

  对甲苯磺酸 、 正戊酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以61%的产率得到N-tosylpentanamide
  参考文献：
  名称：

  Synthesis of Lactones via C–H Functionalization of Nonactivated C(sp³)–H Bonds

  摘要：

  An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp(3))-H bonds through radical 1,5-hydrogen abstraction. The gamma-bromoamides formed are subsequently converted to gamma-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp(3)-hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of gamma-lactones into complex carbon frameworks.

  DOI：

  10.1021/acs.orglett.6b03371

文献信息

• Iodide as an Activating Agent for Acid Chlorides in Acylation Reactions
  作者：Russell J. Wakeham、James E. Taylor、Steven D. Bull、James A. Morris、Jonathan M. J. Williams

  DOI：10.1021/ol400035f

  日期：2013.2.1

  Acid chlorides can be activated using a simple iodide source to undergo nucleophilic attack from a variety of relatively weak nucleophiles. These include Friedel–Crafts acylation of N-methylpyrroles, N-acylation of sulfonamides, and acylation reactions of hindered phenol derivatives. The reaction is believed to proceed through a transient acid iodide intermediate.

  可以使用简单的碘源活化酰氯，使其受到各种相对较弱的亲核试剂的亲核攻击。其中包括N-甲基吡咯的Friedel-Crafts酰化，磺酰胺的N-酰化以及受阻酚衍生物的酰化反应。据信该反应通过过渡性碘酸中间体进行。
• 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。
• Iron-Catalyzed Nitrene Insertion Reaction for Facile Construction of Amide Compounds
  作者：Chi-Ming Che、Guo-Qiang Chen、Zhen-Jiang Xu、Yungen Liu、Cong-Ying Zhou

  DOI：10.1055/s-0030-1260531

  日期：2011.5

  from aldehydes by an iron-catalyzed nitrene insertion reaction has been developed. Both aryl and aliphatic aldehydes can directly afford the corresponding amides with an iron(II)-terpyridine (tpy) complex formed in situ as catalyst, and PhI=NTs as nitrogen source under mild reaction conditions. An ESI-MS study revealed the formation of [Fe(tpy) 2 (NTs)] 2+ as a reaction intermediate.

  已经开发了一种通过铁催化的氮烯插入反应从醛构建酰胺化合物的简便方法。在温和的反应条件下，芳基和脂肪醛都可以直接得到相应的酰胺，以原位形成的铁（II）-三联吡啶（tpy）配合物作为催化剂，PhI=NTs作为氮源。ESI-MS 研究揭示了 [Fe(tpy) 2 (NTs)] 2+ 作为反应中间体的形成。
• Cobalt-Catalyzed Cyclization of Unsaturated <i>N</i>-Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction
  作者：David M. Fischer、Moritz Balkenhohl、Erick M. Carreira

  DOI：10.1021/jacsau.2c00186

  日期：2022.5.23

  The cycloisomerization of β-, γ-, and δ-unsaturated N-acyl sulfonamides to N-sulfonyl lactams and imidates is reported. This transformation is effected in the presence of a CoIII(salen) catalyst using t-BuOOH or air as the oxidant. The method shows good functional group tolerance (alkyl, aryl, heteroaryl, ether, N-Boc) and furnishes an underexplored class of cyclic building blocks. The strong solvent

  报道了β-、γ-和δ-不饱和N-酰基磺酰胺环异构化为N-磺酰基内酰胺和亚胺酸酯。这种转变是在 Co III (salen) 催化剂的存在下使用t -BuOOH 或空气作为氧化剂进行的。该方法显示出良好的官能团耐受性（烷基、芳基、杂芳基、醚、N -Boc），并提供了一类尚未开发的环状结构单元。研究了转化的强溶剂依赖性，并强调了N-磺酰亚胺酯产品类​​的合成多功能性。
• 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.