N,N-二(2-叠氮乙基)-4-甲基苯磺酰胺 | 154875-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,N-二(2-叠氮乙基)-4-甲基苯磺酰胺
• 英文名称: N,N-bis-(2-azidoethyl)-4-methyl-benzenesulfonamide
• 英文别名: N,N-bis(2-azidoethyl)-4-methylbenzenesulfonamide；Benzenesulfonamide, N,N-bis(2-azidoethyl)-4-methyl-
• CAS: 154875-27-1
• 化学式: C₁₁H₁₅N₇O₂S
• 分子量: 309.352
• InChiKey: GNDZKOXYGOPKOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  74.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N-二(2-叠氮乙基)-4-甲基苯磺酰胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以66%的产率得到N,N-二(2-氨基乙基)-4-甲基苯磺酰胺
  参考文献：
  名称：

  Chromogenic Diaza-Crown Ether Dicarboxylic Acids for Determination of Calcium Ions

  摘要：

  The synthesis of two novel calcium chromoionophores 2 and 3, which are based on a benzodiazacrown ether with an inward-facing methoxyl group and bear two acetic acid groups and a 2,4,6-trinitroanilino chromophore, is described. Calcium and magnesium responses at pH optima are determined. Compound 2 exhibits a 31-nm bathochromic shift of the absorption maximum, an increase in the absorptivity upon complexation with Ca2+, and good selecitivity for Ca2+ over Mg2+ at pH 10.3. The response of chromoionophore 2 is linear from 0 to 8 X 10(-3) M Ca2+.

  DOI：

  10.1021/jo00082a019
• 作为产物：
  描述：

  N,N-双[2-(对甲苯磺酰氧基)乙基]-对甲苯磺酰胺 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以82%的产率得到N,N-二(2-叠氮乙基)-4-甲基苯磺酰胺
  参考文献：
  名称：

  Synthesis, Biological Evaluation and Study of the Effect of Various N-Substituents on the Thermal Stabilities of Some New Diethanolamine Derivatives

  摘要：

  二乙醇胺及其衍生物在医药和其他工业产品中具有重要意义。我们合成了一系列新的二乙醇胺衍生物，并通过 1H NMR、13C NMR、傅立叶变换红外光谱和质谱法对其进行了表征。对所有合成化合物进行了体外抗菌测试，以检测它们对病原微生物大肠杆菌、金黄色葡萄球菌、黄体小球菌、铜绿假单胞菌、枯草芽孢杆菌、突变巴斯德菌、根瘤蚜和伤寒沙门氏菌的抗菌活性。在测试的化合物中，发现化合物 2a、2b、2c、3a 和 4b 是最有效的成员，它们抑制了试验中使用的大多数病原体。二乙醇胺必须含有甲苯基或三氟基团才能具有良好的抗菌活性。所有合成的衍生物都表现出平均的 FRAP 活性和相当好的金属螯合活性，在所有测试的衍生物中，化合物 2c 表现出优异的 ABTS 自由基清除能力。通过 TGA 和 DSC 分析，研究了热稳定性以及各种 N 保护基团对选定二乙醇胺衍生物（室温下的自由流动油和固体衍生物 2a）的热稳定性和降解的影响。

  DOI：

  10.14233/ajchem.2013.14543

文献信息

• Metal-Free Route to Carboxylated 1,4-Disubstituted 1,2,3-Triazoles from Methoxycarbonyl-Modified Vinyl Sulfone
  作者：Jayanta Das、Santu Dey、Tanmaya Pathak

  DOI：10.1021/acs.joc.9b02443

  日期：2019.12.6

  A metal-free alternative to the regioselective synthesis of carboxylated 1,4-disubstituted 1,2,3-triazoles (1,4-cDTs) has been accomplished. A methoxycarbonyl-substituted vinyl sulfone on reactions with organic azides resulted in the formation of 1,4-cDTs in an operationally simple route. The reaction, carried out with a variety of organic azides containing free alcohol, acid, Boc-protected amine,

  现已实现了无金属替代方案，可选择性取代羧基化的1,4-二取代1,2,3-三唑（1,4-cDTs）。与有机叠氮化物反应时，甲氧基羰基取代的乙烯基砜导致以操作简单的方式形成1,4-cDTs。发现该反应是使用多种有机叠氮化物进行的，这些有机叠氮化物具有普遍性质，该有机叠氮化物包含游离醇，酸，Boc保护的胺，酯，保护糖，长链烷烃，苄基，9-甲基蒽基和胆固醇基，提供了许多新的化学实体；叠氮化物的反应主要生成所需的产物和一些未预期的产物。本文首次报道了任何1,4-二取代1,2的有针对性的无金属合成，
• A Metal-Free, Aqueous and General Route to 1,5-Disubstituted-1,2,3-triazoles: ‘Reversed Regioisomeric’ 1,3-Dipolar Cycloaddition of Azides and Vinyl Sulfones
  作者：Tanmaya Pathak、Santu Dey、Dhrubajyoti Datta

  DOI：10.1055/s-0030-1260306

  日期：2011.10

  A metal-free, vinyl sulfone-based synthesis of 1,5-disubstituted-1,2,3-triazoles is reported for the first time. These triazoles are easily formed in a regioselective fashion by heating under reflux a mixture of a substituted vinyl sulfone and an organic azide ‘on water’. This powerful and practical route has the potential to be exploited for the synthesis of complex 1,5-disubstituted-1,2,3-triazoles.

  首次报道了一种无金属的基于乙烯基磺酰的1,5-二取代-1,2,3-三唑的合成方法。这些三唑可以通过在水相中加热回流甲基取代的乙烯基磺酰和有机叠氮化合物的混合物，以区域选择性的方式轻易形成。这条强大且实用的路线有潜力用于合成复杂的1,5-二取代-1,2,3-三唑。
• Polymeric Materials Via Click Chemistry
  申请人：Fokin Valery

  公开号：US20080311412A1

  公开（公告）日：2008-12-18

  Adhesive polymers are formed when polyvalent azides and alkynes are assembled into crosslinked polymer networks by copper-catalyzed 1,3-dipolar cycloaddition. The condensation polymerization is efficiently promoted by Cu ions either leached from the metal surface or added to the monomer mixture, and strong interactions with metal surfaces are provided by the multiple triazole binding elements produced. The adhesive polymers may be formed either as adhesive polymer coatings or as adhesive polymer cement.

  当多价叠氮化合物和炔烃通过铜催化的1,3-偶极环加成反应组装成交联聚合物网络时，形成粘合性高分子。铜离子可以从金属表面溶出或添加到单体混合物中，有效促进缩聚聚合反应，并通过产生多个三唑结合元素为金属表面提供强烈的相互作用。这些粘合性高分子可以形成粘合性高分子涂层或粘合性高分子水泥。
• Direct Synthesis of 1,5-Disubstituted-4-magnesio-1,2,3-triazoles, Revisited
  作者：Antoni Krasiński、Valery V. Fokin、K. Barry Sharpless

  DOI：10.1021/ol0499203

  日期：2004.4.1

  [GRAPHICS]After revisiting earlier works reporting the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles via the addition of bromomagnesium acetylides to azides, much improved yields of the products were obtained for a wide array of azides and alkynes. The intermediates of that reaction can be trapped with different electrophiles to regioselectively form 1,4,5-trisubstituted 1,2,3-triazoles.
• Enantiopure 1,4,5-Trisubstituted 1,2,3-Triazoles from Carbohydrates: Applications of Organoselenium Chemistry
  作者：Atanu Bhaumik、Supravat Samanta、Tanmaya Pathak

  DOI：10.1021/jo5009564

  日期：2014.8.1

  A wide range of stable vinyl selenone-modified furanosides has been synthesized for the first time. These 2 pi-partners undergo 1,3-dipolar cycloaddition reactions with a wide range of organic azides to afford enantiopure trisubstituted triazoles. Furanosyl rings opened up during triazole synthesis to generate polyfunctionalized molecules, ready to undergo further transformations. This strategy is one of the most convenient methods for the synthesis of enantiopure 1,4,5-trisubstituted 1,2,3-triazoles where the chiral components are attached to C-4 or C-5 position of triazole ring. These triazoles are formed in a regioselective manner, and several pairs of regioisomeric triazoles have also been synthesized. The approach affords densely functionalized triazoles, which are amenable to further modifications because of the presence of aldehyde and hydroxyl groups. This powerful and practical route adds to the arsenals of chemists and biologists interested in the synthesis and applications of triazoles.