3-pentyl-4H-1,2,4-benzothiadiazine 1,1-dioxide | 40293-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: 3-pentyl-4H-1,2,4-benzothiadiazine 1,1-dioxide
• 英文别名: 3-pentyl-4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide；3-pentyl-4H-1lambda6,2,4-benzothiadiazine 1,1-dioxide；3-pentyl-4H-1λ6,2,4-benzothiadiazine 1,1-dioxide
• CAS: 40293-58-1
• 化学式: C₁₂H₁₆N₂O₂S
• 分子量: 252.337
• InChiKey: JVMPQYRPGCRZQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N'-(2-bromobenzenesulfonyl)hexanamidine 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以86%的产率得到3-pentyl-4H-1,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  Synthetic Utility of Ammonium Salts in a Cu-Catalyzed Three-Component Reaction as a Facile Coupling Partner

  摘要：

  Ammonium salts were found to be a convenient and inexpensive reagent in the Cu-catalyzed three-component reaction with terminal alkynes and sulfonyl or phosphoryl azides leading to N-unprotected amidines. Thus obtained amidines bearing 2-bromobenzenesulfonyl moiety were efficiently cyclized by the Cu-catalyzed intramolecular N-arylation to give an important pharmacophore skeleton of 2H-1,2,4-benzothiadiazine 1,1-dioxides. Conveniently, two tandem catalytic procedures could be readily operated in one pot.

  DOI：

  10.1021/jo802014g

文献信息

• Monzani; Di Bella; Fabio, Farmaco, Edizione Scientifica, 1973, vol. 28, # 2, p. 149 - 156
  作者：Monzani、Di Bella、Fabio、Manicardi

  DOI：——

  日期：——
• A Convenient Synthesis of 2<i>H</i>-1,2,4-Benzothiadiazine 1,1-Dioxides from 2-Aminobenzenesulfonamide and Carboxylic Acids by using Polyphosphoric Acid Trimethylsilyl Ester as Condensing Agent
  作者：Y. Imai、A. Mochizuki、M. Kakimoto

  DOI：10.1055/s-1983-30543

  日期：——
• IMAI, Y.;MOCHIZUKI, A.;KAKIMOTO, M., SYNTHESIS, BRD, 1983, N 10, 851
  作者：IMAI, Y.、MOCHIZUKI, A.、KAKIMOTO, M.

  DOI：——

  日期：——
• Synthetic Utility of Ammonium Salts in a Cu-Catalyzed Three-Component Reaction as a Facile Coupling Partner
  作者：Jinho Kim、S. Yunmi Lee、Junseung Lee、Youngkyu Do、Sukbok Chang

  DOI：10.1021/jo802014g

  日期：2008.12.5

  Ammonium salts were found to be a convenient and inexpensive reagent in the Cu-catalyzed three-component reaction with terminal alkynes and sulfonyl or phosphoryl azides leading to N-unprotected amidines. Thus obtained amidines bearing 2-bromobenzenesulfonyl moiety were efficiently cyclized by the Cu-catalyzed intramolecular N-arylation to give an important pharmacophore skeleton of 2H-1,2,4-benzothiadiazine 1,1-dioxides. Conveniently, two tandem catalytic procedures could be readily operated in one pot.