N-methyl-2-(oct-1-ynyl)benzenesulfonamide

• 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-(oct-1-ynyl)benzenesulfonamide
• 英文别名: N-methyl-2-oct-1-ynylbenzenesulfonamide
• 化学式: C₁₅H₂₁NO₂S
• 分子量: 279.403
• InChiKey: CWLWSYLREQHJIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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-(oct-1-ynyl)benzenesulfonamide 在 silver nitrate 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到3-hexyl-2-methyl-2H-benzo[e][1,2]thiazine 1,1-dioxide
  参考文献：
  名称：

  AgNO3 mediated C–N bond forming reaction: synthesis of 3-substituted benzothiazines as potential COX inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2012.09.102
• 作为产物：
  描述：

  2-碘苯-1-磺酰氯 在 copper(l) iodide 、 10% Pd/C 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙腈 为溶剂， 反应 10.5h， 生成 N-methyl-2-(oct-1-ynyl)benzenesulfonamide
  参考文献：
  名称：

  AgNO3 mediated C–N bond forming reaction: synthesis of 3-substituted benzothiazines as potential COX inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2012.09.102

文献信息

• 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.