N-ethyl-N,4-dimethylbenzenesulfonamide | 57186-68-2

• 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-ethyl-N,4-dimethylbenzenesulfonamide
• CAS: 57186-68-2
• 化学式: C₁₀H₁₅NO₂S
• mdl: MFCD18974076
• 分子量: 213.301
• InChiKey: BMSQWPVGLOCPKB-UHFFFAOYSA-N

物化性质

• 保留指数：
  1952

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-甲基对甲苯磺酰胺 在 indium (III) iodide 、 苯硅烷 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-ethyl-N,4-dimethylbenzenesulfonamide
  参考文献：
  名称：

  Indium Triiodide Catalyzed Reductive Functionalization of Amides via the Single-Stage Treatment of Hydrosilanes and Organosilicon Nucleophiles

  摘要：

  The indium triiodide catalyzed single-stage cascade reaction of N-sutfonyl amides with hydrosilanes and two types of organosilicon nucleophiles such as silyl cyanide and silyl enolates selectively promoted deoxygenative functionalization to give alpha-cyanoamines and beta-aminocarbonyl compounds, respectively.

  DOI：

  10.1021/ol4015317

文献信息

• The Mechanism of Alkene Elimination from Protonated Toluenesulphonamides Generated by Electrospray Ionisation
  作者：Amie Saidykhan、Jenessa Ebert、William H.C. Martin、Richard T. Gallagher、Richard D. Bowen

  DOI：10.1255/ejms.1427

  日期：2016.8

  The positive ion electrospray mass spectra of a range of sulphonamides of general structure CH3C6H4SO2NHR1 [R1 = C n H2n+1 (n = 1–7), C n H2n-1 (n = 3, 4), C6H5, C6H5CH2 and C6H5CH(CH3)] and CH3C6H4SO2NR1R2 [R1, R2 = C n H2n+1 (n = 1–8)] are reported and discussed. The protonated sulphonamides derived from saturated primary and secondary aliphatic amines generally fragment to only a limited extent

  一系列一般结构为 CH3C6H4SO2NHR1 [R1 = C n H2n+1 (n = 1–7), C n H2n-1 (n = 3, 4), C6H5, C6H5CH2 和 C6H5CH( CH3)] 和 CH3C6H4SO2NR1R2 [R1, R2 = C n H2n+1 (n = 1–8)] 进行了报道和讨论。除非通过碰撞激发能量，否则衍生自饱和脂肪族伯胺和仲胺的质子化磺酰胺通常仅在有限程度上碎裂。观察到两种一般的断裂：首先，消除烯烃，C n H2n，通过从氮上的 C n H2n+1 烷基之一夺氢获得；其次，裂解形成 CH3C6H4SO2+。通过研究 [M + H – C n H2n]+ 信号强度随氮上烷基取代基结构的变化，以及监测与从质子化的不对称磺酰胺中丢失不同的烯烃，其中两个不同的烷基与氮相连。这种断裂有利于烷基在直接连接到氮的碳原子上的支化，因此表明它涉及一种机制，其中通
• Eosin Y-Sensitized Photocatalytic Reaction of Tertiary Aliphatic Amines with Arenesulfonyl Chlorides under Visible-Light Irradiation
  作者：Ronghua Zhang、Yuguo Cai、Deli Sun、Song Xu、Qiguang Zhou

  DOI：10.1055/s-0036-1588828

  日期：2017.8

  A mild, practical, and environmentally friendly route to vinyl sulfones and sulfonamides has been developed based on the reaction of aliphatic amines with arenesulfonyl chlorides in the presence of eosin Y as a photocatalyst under visible light. The method permits the selective formation of vinyl sulfones or sulfonamides, depending on the oxidation environment and solvent. A wide range of products

  基于脂肪胺与芳烃磺酰氯在曙红Y作为光催化剂在可见光下的反应，开发了一种温和、实用且环保的乙烯基砜和磺酰胺途径。该方法允许选择性地形成乙烯基砜或磺酰胺，这取决于氧化环境和溶剂。在优化条件下以中等至良好的收率获得了广泛的产品。
• N Alkylation of Tosylamides Using Esters as Primary and Tertiary Alkyl Sources: Mediated by Hydrosilanes Activated by a Ruthenium Catalyst
  作者：Takashi Nishikata、Hideo Nagashima

  DOI：10.1002/anie.201201426

  日期：2012.5.29

  Select your group: Either a primary or tertiary alkyl group can be selectively introduced onto the nitrogen atom of tosylamides in a ruthenium‐catalyzed reaction employing hydrosilanes through a judicious choice in the esters that serve as the alkyl source (see scheme; Ts= 4‐toluenesulfonyl). These N‐alkylation reactions are useful for construction of naturally occurring azacyclic skeletons.

  选择您的基团：在使用氢硅烷的钌催化反应中，可以明智地选择用作烷基源的酯，将伯烷基或叔烷基选择性引入甲苯磺酰胺的氮原子上（参见方案; Ts = 4-甲苯磺酰基）。这些N烷基化反应可用于构建天然存在的氮杂环骨架。
• Debenzylative Sulfonylation of Tertiary Benzylamines Promoted by Visible Light
  作者：Ying Fu、Qing‐Kui Wu、Zhengyin Du

  DOI：10.1002/ejoc.202100144

  日期：2021.3.26

  A visible light photocatalytic debenzylative sulfonylation of tertiary benzylamines is described, affording a series of sulfonamides in high yields. This operationally simple transformation showed high functional group compatibility and wide substrate scope.

  描述了叔苄胺的可见光光催化脱苄基磺酰化，以高收率提供了一系列磺酰胺。该操作简单的转化显示出高官能团相容性和广泛的底物范围。
• Double C–N bond cleavages of <i>N</i>-alkyl 4-oxopiperidinium salts: access to unsymmetrical tertiary sulfonamides
  作者：Ying Fu、Ming-Peng Li、Chun-Zhao Shi、Fang-Rong Li、Zhengyin Du、Congde Huo

  DOI：10.1039/c9ob02107h

  日期：——

  paper, regiospecific, double intraannular C–N bond cleavages of N-alkyl 4-oxopiperidinium salts are presented. The reaction sequence involves a charge-transfer complex, in situ formed between sulfonyl chloride and N-methylmorpholine, which induces S–Cl bond homolysis of sulfonyl chloride, yielding a reactive sulfonyl radical that further induces the double C–N bond cleavages of N-alkyl 4-oxopiperidinium

  在本文中，提出了N-烷基4-氧代哌啶鎓盐的区域特异性双环内C–N键裂解。反应顺序包括一个电荷转移络合物，原位磺酰氯和之间形成Ñ甲基吗啉，磺酰氯，其诱导S-Cl键均裂，产生反应性基团磺酰进一步诱导的双C-N键断裂ñ -烷基4-氧代哌啶鎓盐。如此产生的仲胺被磺酰氯捕获，得到所需的磺酰胺产物。该协议的关键特征是，在无金属和无氧化剂的条件下，一步切割了4-氧杂环哌啶环的两个环内C–N键。