N-(but-3-yn-1-yl)-3,5-difluorobenzenesulfonamide

• 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-(but-3-yn-1-yl)-3,5-difluorobenzenesulfonamide
• 英文别名: N-but-3-ynyl-3,5-difluorobenzenesulfonamide
• 化学式: C₁₀H₉F₂NO₂S
• 分子量: 245.25
• InChiKey: SDQSORBFGOLHKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(but-3-yn-1-yl)-3,5-difluorobenzenesulfonamide 在 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 盐酸羟胺 、 四丁基氟化铵 、 potassium carbonate 、 正丁胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 0.16h， 生成
  参考文献：
  名称：

  Reactivity of Arynes for Arene Dearomatization

  摘要：

  An unprecedented aryne-mediated dearomatization reaction is described. An aryne intermediate generated from arenesulfonyl ynamide-tethered triynes and tetraynes reacts with both the pi-systems of a tethered alkene and the arenesulfonyl group to generate cyclohexa-1,3-diene-containing pentacyclic and hexacyclic frameworks. Density functional theory (DFT) calculations show a nucleophilic dearomatization mechanism involving a zwitterionic intermediate derived from an aryne. A novel halogen effect on the efficiency of the dearomatization and deterrence of aromatization of the cyclohexa-1,3-diene moiety was also observed.

  DOI：

  10.1021/acs.orglett.8b01466
• 作为产物：
  描述：

  3,5-二氟苯磺酰胺 在 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-(but-3-yn-1-yl)-3,5-difluorobenzenesulfonamide
  参考文献：
  名称：

  Reactivity of Arynes for Arene Dearomatization

  摘要：

  An unprecedented aryne-mediated dearomatization reaction is described. An aryne intermediate generated from arenesulfonyl ynamide-tethered triynes and tetraynes reacts with both the pi-systems of a tethered alkene and the arenesulfonyl group to generate cyclohexa-1,3-diene-containing pentacyclic and hexacyclic frameworks. Density functional theory (DFT) calculations show a nucleophilic dearomatization mechanism involving a zwitterionic intermediate derived from an aryne. A novel halogen effect on the efficiency of the dearomatization and deterrence of aromatization of the cyclohexa-1,3-diene moiety was also observed.

  DOI：

  10.1021/acs.orglett.8b01466

文献信息

• Reactivity of Arynes for Arene Dearomatization
  作者：Rajdip Karmakar、Anh Le、Peipei Xie、Yuanzhi Xia、Daesung Lee

  DOI：10.1021/acs.orglett.8b01466

  日期：2018.7.20

  An unprecedented aryne-mediated dearomatization reaction is described. An aryne intermediate generated from arenesulfonyl ynamide-tethered triynes and tetraynes reacts with both the pi-systems of a tethered alkene and the arenesulfonyl group to generate cyclohexa-1,3-diene-containing pentacyclic and hexacyclic frameworks. Density functional theory (DFT) calculations show a nucleophilic dearomatization mechanism involving a zwitterionic intermediate derived from an aryne. A novel halogen effect on the efficiency of the dearomatization and deterrence of aromatization of the cyclohexa-1,3-diene moiety was also observed.