N-2-propenyl-N-(2'-bromoethyl) benzene sulphonamide | 97462-66-3

• 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-2-propenyl-N-(2'-bromoethyl) benzene sulphonamide
• 英文别名: N-(2-bromoethyl)-N-(2-propenyl)bezenesulfonamide；2-bromoethylallyl-sulfonamide；N-(2-bromoethyl)-N-prop-2-enylbenzenesulfonamide
• CAS: 97462-66-3
• 化学式: C₁₁H₁₄BrNO₂S
• 分子量: 304.208
• InChiKey: WWSYOOOBZMCIHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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-2-propenyl-N-(2'-bromoethyl) benzene sulphonamide 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以87%的产率得到N-(phenylsulfonyl)-3-methylpyrrolidine
  参考文献：
  名称：

  自由基环化作为合成吡咯烷的一种方法

  摘要：

  描述了几种溴代烯丙基和二烯丙基取代的磺酰胺的自由基环化。这些环化的区域化学过程取决于与π键相连的取代基的性质。

  DOI：

  10.1016/s0040-4039(00)98485-5
• 作为产物：
  描述：

  N-烯丙基苯磺酰胺 、 1,2-二溴乙烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以39%的产率得到N-2-propenyl-N-(2'-bromoethyl) benzene sulphonamide
  参考文献：
  名称：

  Synthesis of the pyrrolidine ring system by radical cyclization

  摘要：

  DOI：

  10.1021/jo00350a038

文献信息

• Intramolecular homolytic aromatic substitution of alkyl 2-benzimidazolyl sulfones as a means of entry into alkyl radicals for organic synthesis
  作者：David Crich、Daniel Grant

  DOI：10.1016/j.tetlet.2008.02.174

  日期：2008.4

  radical aromatic substitution of heteroaryl sulfones by tethered aryl radicals has been investigated as a source of alkyl radicals. The 1-(2-iodobenzyl)benzimidazole-2-sulfonyl system was found to be the most effective, while a tetrazole-based system did not undergo the desired radical aromatic substitution at all. Application of the benzimidazole-based system to the generation of alkyl radical and their

  杂芳基砜被系链芳基的分子内芳基芳香取代已被研究作为烷基自由基的来源。发现 1-(2-iodobenzyl)benzimidazole-2-sulfonyl 系统是最有效的，而基于四唑的系统根本没有经历所需的自由基芳族取代。证明了基于苯并咪唑的系统在烷基自由基的生成中的应用以及它们随后在自由基环化中的应用。
• PhSeSiR₃-Catalyzed Group Transfer Radical Reactions
  作者：Ganesh Pandey、K. S. S. P. Rao、K. V. Nageshwar Rao

  DOI：10.1021/jo000128z

  日期：2000.7.1

  A novel design for initiating radical-based chemistry in a catalytic fashion is described. The design of the concept is based on the phenylselenyl group transfer reaction from alkyl phenyl selenides by utilizing PhSeSiR3 (1) as a catalytic reagent. The reaction is initiated by the homolytic cleavage of -C-Se- bond of an alkyl phenyl selenide by the in situ generated alkylsilyl radical (R3Si.), obtained by the mesolysis of PhSeSiR3](.-) (1(.-)). The oxidative dimerization of counteranion PhSe- to PhSeSePh functions as radical terminator. The generation of 1(.-) is achieved by the photoinduced electron transfer (PET) promoted reductive activation of 1 through a photosystem comprising of a visible-light (410 nm)-absorbing electron rich DMA as an electron donor and ascorbic acid as a co-oxidant (Figure 1). The optimum mole ratio between the catalyst 1 and alkyl phenyl selenides for successful reaction is established to be 1:10. The generality of the concept is demonstrated by carrying out variety of radical reactions such as cyclization (10, 15-18), intermolecular addition (25), and tandem annulations (32).
• PADWA, A.;NIMMESGERN, HILDEGARD;WONG, G. S. K., J. ORG. CHEM., 1985, 50, N 26, 5620-5627
  作者：PADWA, A.、NIMMESGERN, HILDEGARD、WONG, G. S. K.

  DOI：——

  日期：——
• PADWA, A.;NIMMESGERN, H.;WONG, G. S. K., TETRAHEDRON LETT., 1985, 26, N 8, 957-960
  作者：PADWA, A.、NIMMESGERN, H.、WONG, G. S. K.

  DOI：——

  日期：——