4-bromo-N-butyl-2-fluorobenzenesulfonamide | 1216845-01-0

• 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-N-butyl-2-fluorobenzenesulfonamide
• CAS: 1216845-01-0
• 化学式: C₁₀H₁₃BrFNO₂S
• 分子量: 310.187
• InChiKey: ZKMVLGGJKDNPFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-N-butyl-2-fluorobenzenesulfonamide 在 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.67h， 生成 (S)-8-bromo-2-butyl-5-methyl-2,3,4,5-tetrahydrobenzo[b][1,4,5]oxathiazocine-1,1-dioxide
  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 、 正丁胺 在 三乙胺 作用下， 生成 4-bromo-N-butyl-2-fluorobenzenesulfonamide
  参考文献：
  名称：

  10.1021/0l100035e

  摘要：

  DOI：

  10.1021/0l100035e

文献信息

• Intramolecular monomer-on-monomer (MoM) Mitsunobu cyclization for the synthesis of benzofused thiadiazepine-dioxides
  作者：Pradip K. Maity、Quirin M. Kainz、Saqib Faisal、Alan Rolfe、Thiwanka. B. Samarakoon、Fatima Z. Basha、Oliver Reiser、Paul R. Hanson

  DOI：10.1039/c1cc14807a

  日期：——

  The utilization of a monomer-on-monomer (MoM) intramolecular Mitsunobu cyclization reaction employing norbornenyl-tagged (Nb-tagged) reagents is reported for the synthesis of benzofused thiadiazepine-dioxides. Facile purification was achieved viaring-opening metathesis (ROM) polymerization initiated by one of three metathesis catalyst methods: (i) free metathesis catalyst, (ii) surface-initiated catalyst-armed silica, or (iii) surface-initiated catalyst-armed Co/C magnetic nanoparticles.

  本研究采用降冰片烯标记（Nb-tagged）试剂，利用单体对单体（MoM）分子内 Mitsunobu 环化反应合成苯并二氮杂卓-二氧杂环。通过以下三种元合成催化剂方法中的一种：(i) 游离元合成催化剂；(ii) 表面引发的催化剂铠装二氧化硅；或 (iii) 表面引发的催化剂铠装 Co/C 磁性纳米粒子，实现了viaring-opening元合成（ROM）聚合反应的简便纯化。
• Silica-Supported Oligomeric Benzyl Phosphate (Si-OBP) and Triazole Phosphate (Si-OTP) Alkylating Reagents
  作者：Pradip K. Maity、Saqib Faisal、Alan Rolfe、Diana Stoianova、Paul R. Hanson

  DOI：10.1021/acs.joc.5b01456

  日期：2015.10.16

  The syntheses of silica-supported oligomeric benzyl phosphates (Si-OBPn) and triazole phosphates (Si-OTPn) using ring-opening metathesis polymerization (ROMP) for use as efficient alkylating reagents is reported. Ease of synthesis and grafting onto the surface of norbornenyl-tagged (Nb-tagged) silica particles has been demonstrated for benzyl phosphate and triazole phosphate monomers. It is shown that these silica polymer hybrid reagents, Si-OBPn and Si-OTPn, can be used to carry out alkylation reactions with an array of different nudeophiles to afford the corresponding benzylated and (triazolyl)methylated products in good yield and high purity.
• 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.
• 10.1021/0l100035e
  作者：Rolfe, Alan、Samarakoon, Thiwanka B.、Hanson, Paul R.

  DOI：10.1021/0l100035e

  日期：——
• 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.