[(3-azidobuta-1,2-dienyl)sulfonyl]benzene | 868519-94-2

• 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: [(3-azidobuta-1,2-dienyl)sulfonyl]benzene
• CAS: 868519-94-2
• 化学式: C₁₀H₉N₃O₂S
• 分子量: 235.266
• InChiKey: VVEHURFXDZMAJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  56.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3-azidobuta-1,2-dienyl)sulfonyl]benzene 在 tetramethylguanidinum azide 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 E-(2,3-diazidobut-2-enylsulfonyl)-benzene 、 Z-(2,3-diazidobut-2-enylsulfonyl)-benzene
  参考文献：
  名称：

  First successful synthesis, isolation and characterization of open-chain 1,2-diazidoethenes

  摘要：

  Open-chain 1,2-diazidoethenes have been obtained from the recently reported acceptor-substituted propargyl azides by one-pot reactions with tetramethylguanidinium azide (TMGA) and in some cases via a two-step procedure starting with in situ production of the corresponding azidoallene followed by addition of hydrazoic acid with the help of TMGA. In a different synthetic pathway, the substitution reactions between 2-azido-3-haloacroleins and hexadecyltributylphosphonium azide (QN(3)) have been used. In order to have more evidence for their structures, some diazido compounds were converted to their bis-triazole derivatives through 1,3-dipolar cycloaddition. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.025
• 作为产物：
  描述：

  (3-azidobut-1-ynylsulfonyl)benzene 在 三乙烯二胺 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以19%的产率得到[(3-azidobuta-1,2-dienyl)sulfonyl]benzene
  参考文献：
  名称：

  带有强受体取代基的第一炔丙基叠氮化物及其有效转化为烯丙基叠氮化物：取代基电子效应对炔丙基叠氮化物反应性的影响

  摘要：

  我们已成功合成含有 1- 或 3- 苯硫基官能团的炔丙基叠氮化物。将它们的硫原子选择性氧化为亚砜和砜，可以获得第一个带有受体取代基的炔丙基叠氮化物。有趣的是，后者炔丙基叠氮化物的质子重排导致形成具有相对高稳定性和中等至良好产率的烯基叠氮化物。含有苯硫基官能团的炔丙基叠氮化物在亲核试剂存在下反应，通过短寿命的烯基叠氮化物提供预期的 N-未取代的 1,2,3-三唑。这些结果与相应的亚砜和砜的结果完全不同，它们在类似条件下反应生成相应的双（三唑并）吡嗪衍生物或生成新取代的乙烯基叠氮化物。后一种化合物可以成功地用作原料，提供获得氮丙啶的途径。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejoc.200500135

文献信息

• New Way to Methylene-2H-azirines and Their Use as Powerful Intermediates for the Stereo- and Regioselective Synthesis of Compounds with Vinylamine Substructure
  作者：Joseph Rodolph Fotsing、Klaus Banert

  DOI：10.1002/ejoc.200600302

  日期：2006.8

  New and relatively stable methylene-2H-azirines 1 have been prepared by photolysis of allenyl azides or from 2-halo-2H-azirines by elimination of HX (X = halogen). The reaction of these methylene-2H-azirines with nucleophiles led to the highly stereo- and regio-selective formation of novel 1-aminovinyl derivatives with good to excellent yields. The trapping reactions of the less stable methylene-2H-azirines

  新的和相对稳定的亚甲基-2H-氮丙啶 1 已通过烯基叠氮化物的光解或通过消除 HX（X = 卤素）从 2-卤代-2H-氮丙啶制备。这些亚甲基-2H-氮丙啶与亲核试剂的反应导致高度立体和区域选择性地形成新型 1-氨基乙烯基衍生物，收率良好至极好。较不稳定的亚甲基-2H-氮丙啶的捕集反应产生了类似的结果。此外，我们能够证明之前关于 2-（苯磺酰基）丙烯腈 (9) 的报告是基于不正确的数据。因此，可以认为后一种化合物在本文中首先被描述。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• First Propargyl Azides Bearing Strong Acceptor Substituents and Their Effective Conversion into Allenyl Azides: Influence of the Electronic Effects of Substituents on the Reactivity of Propargyl Azides
  作者：Joseph Rodolph Fotsing、Klaus Banert

  DOI：10.1002/ejoc.200500135

  日期：2005.9

  We have succeeded in the synthesis of propargyl azides containing 1- or 3-phenylthio functionalities. The selective oxidation of their sulfur atoms to sulfoxides and sulfones allows access to the first propargyl azides bearing acceptor substituents. Interestingly, the prototropic rearrangement of the latter propargyl azides leads to the formation of allenyl azides with relatively high stabilities and

  我们已成功合成含有 1- 或 3- 苯硫基官能团的炔丙基叠氮化物。将它们的硫原子选择性氧化为亚砜和砜，可以获得第一个带有受体取代基的炔丙基叠氮化物。有趣的是，后者炔丙基叠氮化物的质子重排导致形成具有相对高稳定性和中等至良好产率的烯基叠氮化物。含有苯硫基官能团的炔丙基叠氮化物在亲核试剂存在下反应，通过短寿命的烯基叠氮化物提供预期的 N-未取代的 1,2,3-三唑。这些结果与相应的亚砜和砜的结果完全不同，它们在类似条件下反应生成相应的双（三唑并）吡嗪衍生物或生成新取代的乙烯基叠氮化物。后一种化合物可以成功地用作原料，提供获得氮丙啶的途径。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• First successful synthesis, isolation and characterization of open-chain 1,2-diazidoethenes
  作者：Joseph Rodolph Fotsing、Manfred Hagedorn、Klaus Banert

  DOI：10.1016/j.tet.2005.07.025

  日期：2005.9

  Open-chain 1,2-diazidoethenes have been obtained from the recently reported acceptor-substituted propargyl azides by one-pot reactions with tetramethylguanidinium azide (TMGA) and in some cases via a two-step procedure starting with in situ production of the corresponding azidoallene followed by addition of hydrazoic acid with the help of TMGA. In a different synthetic pathway, the substitution reactions between 2-azido-3-haloacroleins and hexadecyltributylphosphonium azide (QN(3)) have been used. In order to have more evidence for their structures, some diazido compounds were converted to their bis-triazole derivatives through 1,3-dipolar cycloaddition. (c) 2005 Elsevier Ltd. All rights reserved.