4-fluoro-2-(6-hydroxy-hex-1-ynyl)-N-methyl-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: 4-fluoro-2-(6-hydroxy-hex-1-ynyl)-N-methyl-benzenesulfonamide
• 英文别名: 4-fluoro-2-(6-hydroxy-hex-1-ynyl)-N-methylbenzenesulfonamide；4-fluoro-2-(6-hydroxyhex-1-ynyl)-N-methylbenzenesulfonamide
• 化学式: C₁₃H₁₆FNO₃S
• 分子量: 285.339
• InChiKey: CVZWEGNOMOFJDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-fluoro-2-(6-hydroxy-hex-1-ynyl)-N-methyl-benzenesulfonamide 在 silver hexafluoroantimonate 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以90%的产率得到4-(6-fluoro-2-methyl-1,1-dioxo-1,2-dihydro-1-benzo[e][1,2]thiazin-3-yl)butan-1-ol
  参考文献：
  名称：

  A Remarkable Accelerating Effect of Ag-Salt on Intramolecular Cyclization of o-(1-Alkynyl)benzenesulfonamides

  摘要：

  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.

  DOI：

  10.1021/jo701470h
• 作为产物：
  描述：

  4-fluoro-2-iodo-N-methylbenzenesulfonamide 、 5-己炔-1-醇 在 palladium on activated charcoal copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 10.5h， 以96%的产率得到4-fluoro-2-(6-hydroxy-hex-1-ynyl)-N-methyl-benzenesulfonamide
  参考文献：
  名称：

  A Remarkable Accelerating Effect of Ag-Salt on Intramolecular Cyclization of o-(1-Alkynyl)benzenesulfonamides

  摘要：

  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.

  DOI：

  10.1021/jo701470h

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.
• 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.