N-methyl-2-(phenylethynyl)benzenesulfonamide | 18963-38-7

• 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-methyl-2-(phenylethynyl)benzenesulfonamide
• 英文别名: N-methyl-2-phenylethynyl-benzenesulfonamide；o-(N-Methylsulfamoyl)-tolan；N-methyl-2-(2-phenylethynyl)benzenesulfonamide
• CAS: 18963-38-7
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: LCQUHHRDWJZOSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methyl-2-(phenylethynyl)benzenesulfonamide 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以90%的产率得到2-methyl-3-phenyl-2H-benzo[e][1,2]thiazine-1,1-dioxide
  参考文献：
  名称：

  One-Pot Sonogashira Coupling–Cyclization toward Regioselective Synthesis of Benzosultams

  摘要：

  A one-pot method for the Sonogashira coupling and cyclization of 2-bromobenzenesulfonamides and terminal alkynes is presented. This method allows access to a variety of substituted benzosultams regioselectively in excellent yields. The reasons for regioselectivity are interpreted through density functional theory (DFT) studies.

  DOI：

  10.1021/acs.joc.5b00274
• 作为产物：
  描述：

  2-溴-N-甲基苯磺酰胺 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以91%的产率得到N-methyl-2-(phenylethynyl)benzenesulfonamide
  参考文献：
  名称：

  One-Pot Sonogashira Coupling–Cyclization toward Regioselective Synthesis of Benzosultams

  摘要：

  A one-pot method for the Sonogashira coupling and cyclization of 2-bromobenzenesulfonamides and terminal alkynes is presented. This method allows access to a variety of substituted benzosultams regioselectively in excellent yields. The reasons for regioselectivity are interpreted through density functional theory (DFT) studies.

  DOI：

  10.1021/acs.joc.5b00274

文献信息

• A palladium-catalyzed reaction of 2-alkynylbromobenzene with 2-(2-alkynyl)benzenesulfonamide
  作者：Qing Xiao、Yong Luo、Yujun Yan、Qiuping Ding、Jie Wu

  DOI：10.1039/c3ra40582f

  日期：——

  A palladium-catalyzed reaction of 2-alkynylbromobenzene with 2-(2-alkynyl)benzenesulfonamide has been developed, which gives rise to 6H-benzo[f]indeno[1,2-d][1,2]thiazepine 5,5-dioxides in good yields.

  在钯催化下，2-炔基溴苯与 2-(2-炔基)苯磺酰胺发生了反应，从而以良好的收率生成了 6H-苯并[f]茚并[1,2-d][1,2]硫氮杂卓 5,5- 二氧化物。
• Generation of 4-((trifluoromethyl)thio)-2H-benzo[e][1,2]thiazine 1,1-dioxides via a reaction of trifluoromethanesulfanylamide with 2-(2-alkynyl)benzenesulfonamide
  作者：Qing Xiao、Jie Sheng、Zhiyuan Chen、Jie Wu

  DOI：10.1039/c3cc44263b

  日期：——

  The incorporation of the (trifluoromethyl)thio group into the benzo[e][1,2]thiazine 1,1-dioxide scaffold via a reaction of trifluoromethanesulfanylamide with 2-(2-alkynyl)benzenesulfonamide is reported. The transformation proceeds under mild conditions to afford the 4-((trifluoromethyl)thio)-2H-benzo[e][1,2]thiazine 1,1-dioxides in moderate to good yields.

  据报道，通过三氟甲磺酰胺与2-(2-炔基)苯磺酰胺的反应将(三氟甲基)硫基引入苯并[e][1,2]噻嗪1,1-二氧化物支架中。转化在温和条件下进行，以中等至良好的产率提供 4-((三氟甲基)硫基)-2H-苯并[e][1,2]噻嗪 1,1-二氧化物。
• Generation of 6H-benzo[f]cyclopenta[d][1,2]thiazepine 5,5-dioxides via a palladium-catalyzed reaction of 2-(2-alkynyl)benzenesulfonamide
  作者：Huanhuan Wang、Yong Luo、Xiufeng Hou、Jie Wu

  DOI：10.1039/c2dt32452k

  日期：——

  An efficient approach for the assembly of 6H-benzo[f]cyclopenta[d][1,2]thiazepine 5,5-dioxides via a palladium-catalyzed tandem reaction of 2-(2-alkynyl)benzenesulfonamide with 2-alkynylvinyl bromide is reported. This transformation proceeds smoothly through a double carbopalladation with high efficiency.

  通过2-（2-炔基）苯磺酰胺与2-炔基乙烯基溴的钯的串联反应组装6 H-苯并[ f ]环戊五[ d ] [1,2]噻氮平5,5-二氧化物的有效方法被报道。这种转变通过高效的双碳纤维化而顺利进行。
• A Remarkable Accelerating Effect of Ag-Salt on Intramolecular Cyclization of <i>o</i>-(1-Alkynyl)benzenesulfonamides
  作者：Deepak Kumar Barange、T. C. Nishad、N. Kumara Swamy、Venkanna Bandameedi、Dinesh Kumar、Bukkapattanam R. Sreekanth、K. Vyas、Manojit Pal

  DOI：10.1021/jo701470h

  日期：2007.10.1

  Herein, we report transition metal-catalyzed intramolecular cyclization of o-(1-alkynyl)benzenesulfonamides to afford 3-substituted benzothiazines regioselectively via a C-N bond forming reaction and Cu-catalyzed sequential C-N and C-C bond formation leading to the corresponding 3,4-disubstituted derivatives.
• AgNO3 mediated C–N bond forming reaction: synthesis of 3-substituted benzothiazines as potential COX inhibitors
  作者：D. Rambabu、P.V.N.S. Murthy、K.R.S. Prasad、Ajit Kandale、Girdhar Singh Deora、M.V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.tetlet.2012.09.102

  日期：2012.11

  AgNO3 facilitated the intramolecular ring closure of o-(1-alkynyl)benzenesulfonamides via a regioselective C-N bond forming reaction leading to the formation of 3-substituted benzothiazine derivatives. A number of compounds were prepared in good yields by using this inexpensive and safe methodology. All the compounds synthesized were evaluated for their cyclooxygenase (COX) inhibiting properties in vitro. A number of compounds that do not contain an enolic hydroxyl group showed selectivities toward COX-2 over COX-1 inhibition. This was further supported by the predictive binding mode of two compounds with COX-1 and -2 proteins through molecular docking studies. (C) 2012 Elsevier Ltd. All rights reserved.