N-(methylsulfonyl)-N-phenylacetamide | 3700-65-0

• 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-(methylsulfonyl)-N-phenylacetamide
• 英文别名: N-mesyl-N-phenylacetamide；N-Acetyl-N-phenyl-methansulfonamid；N-acetyl-N-methanesulfonyl-aniline；N-Methansulfonyl-acetanilid；N-Acetyl-N-methansulfonyl-anilin；N-Acetyl-methanesulfonilide；N-methylsulfonyl-N-phenylacetamide
• CAS: 3700-65-0
• 化学式: C₉H₁₁NO₃S
• 分子量: 213.257
• InChiKey: HDQFXPQWUILPAF-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  332.2±25.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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-(methylsulfonyl)-N-phenylacetamide 在 dimethyltitanocene 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 N-苯基甲磺酰胺
  参考文献：
  名称：

  Sequential N-acylamide methylenation–enamide ring-closing metathesis: a synthetic entry to 1,4-dihydroquinolines

  摘要：

  A new synthetic entry to the 1,4-dihydroquinoline nucleus is reported. The procedure involves the dimethyltitanocene methylenation of N-(alkoxycarbonyl)amides derived from 2-allylanilines, followed by ring-closing metathesis of the resulting enamides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.028
• 作为产物：
  描述：

  苯胺 在 zinc oxide-nanoparticle 作用下， 反应 1.75h， 生成 N-(methylsulfonyl)-N-phenylacetamide
  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

• Infrared Spectra of Phenylsulfonyl Derivatives. (4). The Infrared Spectra of N-Acylsulfonamide Derivatives. (Organic Analysis. XLVIII)
  作者：Yo Ueda、Hiroshige Yano、Tsutomu Momose

  DOI：10.1248/cpb.12.5

  日期：——

  The splitting phenomenon of the carbonyl absorptions and the shifts of S-N stretching vibrations to a longer wave length region of some N-acyl-N-substituted-sulfonamide derivatives measured in solid state were described. Tertiary sulfonamides had their SO2 stretching vibrations at a shorter wave length region than secondary sulfonamides. N-Acetyl-N-alkylmethane (or ethane) sulfonamide showed strong C-N stretching vibrations of the group N-CH2-R at about 1125cm-1. N-Acyl-N-substituted-sulfonamide derivatives had very strong asymmetric stretching vibrations of the group C-CO-N at 1250∼1290cm-1. Synthesis of some sulfonamide derivatives is also described.

  在固态下测得的某些N-酰基-N-取代磺酰胺衍生物的羰基吸收分裂现象以及S-N伸缩振动向长波长区域的位移均有所描述。三级磺酰胺的SO2伸缩振动比二级磺酰胺位于更短的波长区域。N-乙酰基-N-烷基甲烷(或乙烷)磺酰胺在约1125cm-1处显示出强烈的N-CH2-R基团的C-N伸缩振动。N-酰基-N-取代磺酰胺衍生物在1250∼1290cm-1处具有非常强烈的C-CO-N基团的不对称伸缩振动。此外，还描述了一些磺酰胺衍生物的合成。
• One-Pot Synthesis of α-Ketoamides from α-Keto Acids and Amines Using Ynamides as Coupling Reagents
  作者：Jianting Ma、Xue Cui、Junyu Xu、Yinfeng Tan、Yan Wang、Xuesong Wang、Youbin Li

  DOI：10.1021/acs.joc.1c02453

  日期：2022.3.4

  A one-pot strategy for α-keto amide bond formation have been developed by using ynamides as coupling reagents under extremely mild reaction conditions. Diversely structural α-ketoamides were afforded in up to 98% yield for 36 examples. This reaction features advantages such as practical coupling procedure, wide functional group tolerance, and extremely mild conditions and has potential applications

  通过在极其温和的反应条件下使用ynamides作为偶联试剂，开发了一种α-酮酰胺键形成的一锅法。对于 36 个实例，不同结构的 α-酮酰胺的产率高达 98%。该反应具有偶联过程实用、官能团耐受性广、条件极其温和等优点，在合成和药物化学中具有潜在的应用价值。
• Catalyst-Free [4+2] Cycloaddition of Ynamides with 2-Halomethyl Phenols To Construct 2-Amino-4<i>H</i>-Chromenes and α-Halo Enamides Simultaneously
  作者：Hao Wen、Weibo Yan、Ping Chen、Yu Li、Yu Tang

  DOI：10.1021/acs.joc.0c01258

  日期：2020.10.16

  We report the development of a facile protocol for the [4+2] cycloaddition of ynamides and 2-halomethyl phenols to afford the corresponding 2-amino-4H-chromenes and α-halo enamides under catalyst-free conditions. The reaction proceeds under mild conditions and exhibits good tolerance toward various functional groups and generates high yields. The plausible mechanism involves the formation of an active

  我们报道了在无催化剂条件下为酰胺和2-卤代甲基苯酚的[4 + 2]环加成反应提供相应的2-氨基-4 H-色烯和α-卤代酰胺的简便方案的发展。反应在温和的条件下进行，对各种官能团表现出良好的耐受性，并产生高收率。可能的机理包括活性中间体酮亚胺以及邻亚甲基醌的形成。
• Metal-triflate ionic liquid systems immobilized onto mesoporous MS41 materials as new and efficient catalysts for N-acylation
  作者：S COMAN、M FLOREA、V PARVULESCU、V DAVID、A MEDVEDOVICI、D DEVOS、P JACOBS、G PONCELET、P GRANGE

  DOI：10.1016/j.jcat.2007.04.022

  日期：2007.7.25

  N-sorption measurements, TG–DTA, DRIFT, XPS, TEM, and ICP-AES. The catalysts were tested in acylation of amines and sulfonamides and proved highly active and selective. For both aromatic and aliphatic amines, acylation with carboxylic acids was possible. For sulfonamides, acylation was possible only with anhydrides. Recycling the catalysts was not accompanied by any leaching of ILs or metal triflate.

  采用接枝法制备了两种基于二氢咪唑鎓和吡啶鎓阳离子的固定MS41离子液体(IL)。三氟甲磺酸盐在这些材料上的第二次固定导致金属-三氟甲磺酸盐复合物固定到离子液体中。由此获得的材料通过 1H NMR、XRD、N-吸附测量、TG-DTA、DRIFT、XPS、TEM 和 ICP-AES 进行表征。该催化剂在胺和磺酰胺的酰化反应中进行了测试，证明具有高活性和选择性。对于芳香胺和脂肪胺，都可以用羧酸进行酰化。对于磺酰胺类药物，只能用酸酐进行酰化。催化剂的回收不伴随离子液体或金属三氟甲磺酸盐的任何浸出。
• Ferric Chloride-Mediated Transacylation of <i>N</i>-Acylsulfonamides
  作者：Dayong Sang、Bingqian Dong、Kangkang Yu、Juan Tian

  DOI：10.1021/acs.joc.3c02288

  日期：2024.2.16

  Transacylation of N-acylsulfonamides, which replaces the N-acyl group with a new one, is a challenging and underdeveloped fundamental transformation. Herein, a general method for transacylation of N-acylsulfonamides is presented. The transformation is enabled by coincident catalytic reactivities of FeCl3 for nonhydrolytic deacylation of N-acylsulfonamides and subsequent acylation of the resultant sulfonamides

  N-酰基磺酰胺的酰基转移，即用一个新的 N-酰基取代N-酰基，是一种具有挑战性且尚未发展的根本性转变。本文提出了N-酰基磺酰胺转酰基的一般方法。该转化是通过FeCl 3对N-酰基磺酰胺的非水解脱酰化和随后所得磺酰胺的酰化的同时催化反应性实现的，并且可以逐步或以一锅方式进行。 GaCl 3和RuCl 3 · xH 2 O对该反应同样有效。该方法温和、高效、操作简单。各种官能团（例如卤素、酮、硝基、氰基、醚和酯）具有良好的耐受性，从而提供良好至优异的收率的转酰化产物。