1-(phenylsulfonyl)-2-p-tolyldiazene | 26272-72-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 炔丙基型1，3-偶极有机化合物
• 英文名称: 1-(phenylsulfonyl)-2-p-tolyldiazene
• 英文别名: (4-methylphenyl)azo phenyl sulfone；p-tolylazo phenyl sulfone；benzenesulfonyl-p-tolyl-diazene；Benzolsulfonyl-p-tolyl-diazen；p-Toluoldiazo-phenylsulfon；N'-Benzolsulfonyl-N-p-tolyl-diimid；N-(4-methylphenyl)iminobenzenesulfonamide
• CAS: 26272-72-0
• 化学式: C₁₃H₁₂N₂O₂S
• 分子量: 260.316
• InChiKey: MHXANCKWNJXVLD-UHFFFAOYSA-N

物化性质

• 熔点：
  82-83 °C
• 沸点：
  411.5±38.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(phenylsulfonyl)-2-p-tolyldiazene 在 四(三苯基膦)钯 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 三苯乙烯
  参考文献：
  名称：

  在钯 (0) 催化下芳基并芳基砜对烯烃的芳基化

  摘要：

  在 80°C 下，芳基偶氮芳基砜与烯烃在苯中的钯 (0) 催化反应以良好的收率得到芳基取代的烯烃。二芳基钯 (II) 物种被提议作为该反应的中间体。

  DOI：

  10.1246/bcsj.61.3575
• 作为产物：
  描述：

  苯磺酰胺 在 氢氧化钾 、 氯化重氮苯 作用下， 生成 1-(phenylsulfonyl)-2-p-tolyldiazene
  参考文献：
  名称：

  Dutt; Whitehead; Wormall, Journal of the Chemical Society, 1921, vol. 119, p. 2090

  摘要：

  DOI：

文献信息

• Copper-catalyzed synthesis of aryldiazo sulfones from arylhydrazines and sulfonyl chlorides under mild conditions
  作者：Jin-Biao Liu、Fu-Jiao Chen、En Liu、Jin-Hui Li、Guanyinsheng Qiu

  DOI：10.1039/c5nj01760b

  日期：——

  this paper, aryldiazo sulfones are prepared from tandem sulfonylation/dehydrogenation reactions of arylhydrazines and sulfonyl chlorides. The transformations proceed well in the presence of catalytic CuSO4·5H2O, leading to aryldiazo sulfones in good to excellent yields. It is believed that this protocol represents a safe and convenient model for the synthesis of these versatile aryldiazo sulfones under

  本文通过芳基肼与磺酰氯的串联磺酰化/脱氢反应制备芳基重氮砜。在催化性CuSO 4 ·5H 2 O的存在下，转化过程进行得很好，从而导致芳基重氮砜的收率很好。据信，该方案代表了在温和条件下合成这些多用途芳基重氮砜的安全方便的模型。
• Reaction of Arylazo Aryl Sulfone with Olefins in the Presence of Tetrakis(triphenylphosphine)palladium(0)
  作者：Nobumasa Kamigata、Tetsuya Kondoh、Masayuki Kameyama、Takeshi Satoh、Michio Kobayashi

  DOI：10.1246/cl.1987.347

  日期：1987.2.5

  Catalytic reaction of arylazo aryl sulfone with olefins in the presence of tetrakis(triphenylphosphine)palladium(0) was investigated. Arylation of olefins was the major product, and 1:1 adduct of arylazo and arenesulfonyl group to olefins was obtained as minor product. Diarylpalladium(II) species was proposed as an intermediate in this reaction.

  研究了在四（三苯基膦）钯 (0) 存在下芳基偶氮芳基砜与烯烃的催化反应。烯烃的芳基化是主要产物，芳基偶氮和芳烃磺酰基与烯烃的 1:1 加合物作为次要产物得到。二芳基钯 (II) 物种被提议作为该反应的中间体。
• ESR parameters of 5,5-dimethylpyrrolidine 1-oxide (DMPO) spin adducts in the photochemical decomposition of azo compounds
  作者：Vladimir Cholvad、Katarina Szaboova、Andrej Staško、Oskar Nuyken、Brigitte Voit

  DOI：10.1002/mrc.1260290421

  日期：1991.4

  Splitting constants and g values are reported for 5,5‐dimethylpyrrolidine 1‐oxide spin adducts with radicals such as substituted‐Ph˙, NaSO3˙, PhS2˙, and others observed in the photochemical decomposition of azo compounds in various solvents.

  报告了 5,5-二甲基吡咯烷 1-氧化物自旋加合物的分裂常数和 g 值，该加合物具有取代的 Ph·、NaSO3·、PhS2· 等自由基，这些自由基在偶氮化合物在各种溶剂中的光化学分解中观察到。
• The Reaction of Arylazo Aryl Sulfones with Carbon Monoxide and Nucleophiles Catalyzed by the Palladium(0) Complex
  作者：Nobumasa Kamigata、Akira Satoh、Masato Yoshida、Masayuki Kameyama

  DOI：10.1246/bcsj.62.605

  日期：1989.2

  The reaction of arylazo aryl sulfone (1) with carbon monoxide in the presence of the palladium(0) catalyst affords substituted benzoic acid in a good yield, together with minor yields of diaryl ketone and biaryl. The reactions of 1 with carbon monoxide and such nucleophiles as alcohols and amines under similar conditions give esters and amides, respectively.

  在钯(0)催化剂的存在下，芳基偶氮芳基砜(1)与一氧化碳的反应以良好的产率得到取代的苯甲酸，同时产生少量的二芳基酮和联芳基。1 与一氧化碳和醇和胺等亲核试剂在相似条件下反应分别生成酯和酰胺。
• Reactions of arylazosulfones with the conjugate bases of (tert-butoxycarbonyl)methyl and tosylmethyl isocyanide. Synthesis of substituted 1-arylimidazoles
  作者：Carlo Dell'Erba、Marino Novi、Giovanni Petrillo、Cinzia Tavani

  DOI：10.1016/s0040-4020(96)01108-8

  日期：1997.2

  The reactions of arylazosulfones 1 (ArN=NSO2Ar') with the potassium salts of (tert-butoxycarbonyl)methyl 2 and tosylmethyl isocyanide 3 in DMSO afford 4,5-bis(tert-butoxycarbonyl)-4 and 4-tosyl-1-arylimidazoles 5, respectively. Yields of imidazoles 4 and 5 vary from moderate to excellent depending on the nature both of Ar in 1 and of the nucleophile (2 or 3) employed. A comparison of the results obtained with those relevant to the reactions of the same nucleophiles with nitrosobenzene in analogous experimental conditions provides useful mechanistic indications on the transformation of 1 to 4 or 5. (C) 1997, Elsevier Science Ltd.