4-bromo-2-fluoro-N-(prop-2-ynyl)benzenesulfonamide | 1225040-03-8

• 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-bromo-2-fluoro-N-(prop-2-ynyl)benzenesulfonamide
• 英文别名: 4-bromo-2-fluoro-N-prop-2-ynylbenzenesulfonamide
• CAS: 1225040-03-8
• 化学式: C₉H₇BrFNO₂S
• 分子量: 292.128
• InChiKey: FSRCUGWWPXZNJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-bromo-2-fluoro-N-(prop-2-ynyl)benzenesulfonamide 在 sodium azide 、 18-冠醚-6 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.17h， 生成 (S)-ethyl 2-(9-bromo-6,6-dioxidobenzo[f][1,2,3]triazolo[5,1-d][1,2,5]thiadiazepin-5(4H)-yl)propanoate
  参考文献：
  名称：

  A Modular Reaction Pairing Approach to the Diversity-Oriented Synthesis of Fused- and Bridged-Polycyclic Sultams

  摘要：

  A reaction pairing strategy centered on utilization of a reaction triad (sulfonylation, SNAr addition and Mitsunobu alkylation) generating skeletally diverse, tricyclic and bicyclic benzofused sultams is reported. Pairing sulfonylation and SNAr reactions yields bridged, tricyclic and bicyclic benzofused sultams. Application of the Mitsunobu reaction in a sulfonylation-Mitsunobu-SNAr pairing allows access to benzthiazocine-1,1-dioxides, while a simple change in the order of pairing to sulfonylation-SNAr-Mitsunobu affords structurally different, bridged tricyclic benzofused sultams.

  DOI：

  10.1021/ol201962n
• 作为产物：
  描述：

  4-溴-2-氟苯磺酰氯 、 炔丙胺 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以88%的产率得到4-bromo-2-fluoro-N-(prop-2-ynyl)benzenesulfonamide
  参考文献：
  名称：

  A Modular Reaction Pairing Approach to the Diversity-Oriented Synthesis of Fused- and Bridged-Polycyclic Sultams

  摘要：

  A reaction pairing strategy centered on utilization of a reaction triad (sulfonylation, SNAr addition and Mitsunobu alkylation) generating skeletally diverse, tricyclic and bicyclic benzofused sultams is reported. Pairing sulfonylation and SNAr reactions yields bridged, tricyclic and bicyclic benzofused sultams. Application of the Mitsunobu reaction in a sulfonylation-Mitsunobu-SNAr pairing allows access to benzthiazocine-1,1-dioxides, while a simple change in the order of pairing to sulfonylation-SNAr-Mitsunobu affords structurally different, bridged tricyclic benzofused sultams.

  DOI：

  10.1021/ol201962n

文献信息

• A Formal [4 + 4] Complementary Ambiphile Pairing Reaction: A New Cyclization Pathway for <i>ortho</i>-Quinone Methides
  作者：Thiwanka B. Samarakoon、Moon Y. Hur、Ryan D. Kurtz、Paul R. Hanson

  DOI：10.1021/ol100495w

  日期：2010.5.21

  A formal, one-pot [4 + 4] cyclization pathway for the generation of eight-membered sultams via in situ generation of an ortho-quinone methide (o-QM) is reported. The pairing of ambiphilic synthons in a complementary fashion is examined whereby o-fluorobenzenesulfonamides are merged with in situ generated o-QM in a formal [4 + 4] cyclization pathway to afford 5,2,1-dibenzooxathiazocine-2,2-dioxide scaffolds under microwave (mW) conditions. The method reported represents the first use of an o-QM in a formal hetero [4 + 4] cyclization.
• A Modular Reaction Pairing Approach to the Diversity-Oriented Synthesis of Fused- and Bridged-Polycyclic Sultams
  作者：Thiwanka B. Samarakoon、Joanna K. Loh、Alan Rolfe、Lisa S. Le、Sun Young Yoon、Gerald H. Lushington、Paul. R. Hanson

  DOI：10.1021/ol201962n

  日期：2011.10.7

  A reaction pairing strategy centered on utilization of a reaction triad (sulfonylation, SNAr addition and Mitsunobu alkylation) generating skeletally diverse, tricyclic and bicyclic benzofused sultams is reported. Pairing sulfonylation and SNAr reactions yields bridged, tricyclic and bicyclic benzofused sultams. Application of the Mitsunobu reaction in a sulfonylation-Mitsunobu-SNAr pairing allows access to benzthiazocine-1,1-dioxides, while a simple change in the order of pairing to sulfonylation-SNAr-Mitsunobu affords structurally different, bridged tricyclic benzofused sultams.