N,N-diallyl-2-bromobenzenesulfonamide | 209543-18-0

• 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: N,N-diallyl-2-bromobenzenesulfonamide
• 英文别名: 2-bromo-N,N-bis(prop-2-enyl)benzenesulfonamide
• CAS: 209543-18-0
• 化学式: C₁₂H₁₄BrNO₂S
• mdl: MFCD09029846
• 分子量: 316.219
• InChiKey: AMEDHJCSPBBHPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  393.5±52.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-diallyl-2-bromobenzenesulfonamide 在 Grubbs catalyst first generation sodium hydride 作用下， 以 甲苯 为溶剂， 以88%的产率得到1-(2-bromobenzenesulfonyl)-2,3-dihydro-1H-pyrrole
  参考文献：
  名称：

  Synthesis of Polycyclic Lactams and Sultams by a Cascade Ring-Closure Metathesis/Isomerization and Subsequent Radical Cyclization

  摘要：

  从易得的底物出发，设计了一种新的一步法程序来制备多环内酰胺和内磺酰胺。通过环闭重排和随后由钌氢复合物促进的异构化，获得的2-吡咯啉可以进行自由基环化，良好产率地生成多环内酰胺。该过程成功应用于双丙烯基磺酰胺，生成相应的内磺酰胺。

  DOI：

  10.1055/s-2005-862386
• 作为产物：
  描述：

  2-溴苯磺酰氯 、 二烯丙基胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到N,N-diallyl-2-bromobenzenesulfonamide
  参考文献：
  名称：

  Synthesis of Polycyclic Lactams and Sultams by a Cascade Ring-Closure Metathesis/Isomerization and Subsequent Radical Cyclization

  摘要：

  从易得的底物出发，设计了一种新的一步法程序来制备多环内酰胺和内磺酰胺。通过环闭重排和随后由钌氢复合物促进的异构化，获得的2-吡咯啉可以进行自由基环化，良好产率地生成多环内酰胺。该过程成功应用于双丙烯基磺酰胺，生成相应的内磺酰胺。

  DOI：

  10.1055/s-2005-862386

文献信息

• Synthesis of conformationally restricted sulfonamides via radical cyclisation
  作者：D. Biswas、L. Samp、A.K. Ganguly

  DOI：10.1016/j.tetlet.2010.03.089

  日期：2010.5

  A convenient synthesis of conformationally restricted sulfonamides such as compounds (12) and (40) with seven- and eight-membered ring structures has been achieved using radical reaction. These compounds and their analogs are expected to serve as important pharmacophores in drug discovery.

  使用自由基反应已经实现了构象受限的磺酰胺如具有七元和八元环结构的化合物（12）和（40）的方便的合成。这些化合物及其类似物有望在药物发现中用作重要的药效团。
• Double Reduction of Cyclic Aromatic Sulfonamides:  A Novel Method for the Synthesis of 2- and 3-Aryl-Substituted Cyclic Amines
  作者：Paul Evans、Thomas McCabe、Ben S. Morgan、Sophie Reau

  DOI：10.1021/ol0480123

  日期：2005.1.1

  The facile double reduction of bicyclic aromatic sulfonamides was used to synthesize a variety of 2- and 3-aryl-substituted pyrrolidines and 2-phenylpiperidine. The method features a combined nitrogen protection and a traceless tether for the transposition of the aromatic moiety from nitrogen to carbon.
• Merging Cross-Metathesis and Radical Cyclization: A Straightforward Access to 4-Substituted Benzosultams
  作者：Olivier Piva、Sophie Feuillastre、Béatrice Pelotier

  DOI：10.1055/s-0032-1318147

  日期：——

  N-Alkyl-N-allyl-2-bromobenzenesulfonamides were functionalized by selective E-cross-metathesis with various alkenes. Subsequent radical cyclization initiated by 2,2'-azobis(iso-butyronitrile) and tris(trimethylsilyl) silane gave the corresponding 4-substituted benzosultams directly in moderate-to-good yields.
• Bimetallic catalytic cascade ring closing metathesis—intramolecular Heck reactions using a fluorous biphasic solvent system or a polymer-supported palladium catalyst
  作者：Ronald Grigg、Mark York

  DOI：10.1016/s0040-4039(00)01250-8

  日期：2000.9

  The combination of ring closing metathesis and intramolecular Heck reactions in a cascade gives bridged ring systems in good yield. Two methods using either a fluorous biphasic solvent system or a polymer-supported palladium catalyst overcome the observed incompatibility of the catalysts. (C) 2000 Elsevier Science Ltd, All rights reserved.
• Sequential and cascade olefin metathesis — intramolecular Heck reaction
  作者：Ronald Grigg、Visuvanathan Sridharan、Mark York

  DOI：10.1016/s0040-4039(98)00709-6

  日期：1998.6

  The sequential or cascade combination of olefin metathesis with intramolecular Heck reactions provides access to fused-, bridged-and spiro-cyclic ring systems in good yield. (C) 1998 Elsevier Science Ltd. All rights reserved.