(2-chlorophenyl)azo 4-methylphenyl sulfone | 60095-84-3

• 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: (2-chlorophenyl)azo 4-methylphenyl sulfone
• 英文别名: 1-(2-chlorophenyl)-2-tosyldiazene；N-(2-chlorophenyl)imino-4-methylbenzenesulfonamide
• CAS: 60095-84-3
• 化学式: C₁₃H₁₁ClN₂O₂S
• 分子量: 294.762
• InChiKey: FRRIIOGQWNRCQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  58.86
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  lithium n-butylselenolate 、 (2-chlorophenyl)azo 4-methylphenyl sulfone 在 18-冠醚-6 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以42%的产率得到1-butylselanyl-2-chlorobenzene
  参考文献：
  名称：

  Aryl arylazo sulfones chemistry. 2. Reactivity toward alkaline alkane- and arene selenolate and alkane- and arenetellurolate anions

  摘要：

  DOI：

  10.1021/jo00376a027
• 作为产物：
  描述：

  对甲苯磺酰氯 在 potassium carbonate 、 copper(II) sulfate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.17h， 生成 (2-chlorophenyl)azo 4-methylphenyl sulfone
  参考文献：
  名称：

  铁（III）催化的烯烃加氢胺化模块化合成烷基芳基偶氮化合物

  摘要：

  已经成功开发了一种新的用芳基重氮砜进行铁催化的烯烃加氢胺化反应，以得到烷基芳基偶氮化合物。芳基重氮砜被用作自由基受体，当芳烃磺酰基离开时，N–N双键将被再生。该反应具有温和的反应条件和广泛的底物范围，从而允许获得许多使用其他方法难以或可能无法获得的偶氮化合物。

  DOI：

  10.1021/acs.orglett.9b00540

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。
• Pyridine‐Catalysed Desulfonylative Addition of β‐Diketones to Arylazosulfones via Diaziridine Rearrangement
  作者：Xin Ji、Ling‐Guo Meng、Hailong Xu、Lei Wang

  DOI：10.1002/adsc.202001171

  日期：2021.2.16

  pyridine‐catalysed desulfonylative addition of β‐diketones to arylazosulfones was developed to obtain diazenyl β‐dicarbonyl compounds. The aryldiazenyl group was observed in the desired product from arylazosulfones, and this diazenylation reaction was achieved via a possible rearrangement process based on diaziridine ring cleavage. The scope of the protocol was investigated and a plausible mechanism was

  开发了吡啶催化的β-二酮向芳基偶氮砜的脱磺酰基加成反应，以获得二氮烯基β-二羰基化合物。在所需的芳基偶氮砜产物中观察到芳基二氮烯基，该二氮烯基化反应是通过基于二氮丙啶环裂解的可能的重排过程实现的。研究了协议的范围，并给出了合理的机制。
• A Direct Route to Tetrahydropyridazine Derivatives via DMAP‐Catalyzed [4+2] Annulation of Allenoates with Arylazosulfones
  作者：Xin Ji、Ziyang Li、Jinfeng Zhang、Yicheng Zhang、Ling‐Guo Meng

  DOI：10.1002/cjoc.202300369

  日期：2023.11.15

  Herein, a DMAP-catalyzed [4+2] annulation of α-substituted allenoates with arylazosulfones is reported, which affords facile access to tetrahydropyridazine derivative in synthetically useful yields. This reaction features mild conditions and good functional group tolerance. Moreover, the resultant products can be readily transformed into pyridazin-3-one derivatives in the presence of DDQ.

  在此，报道了 DMAP 催化的 α-取代的联烯酸酯与芳基偶氮砜的[4+2]环化，这使得能够以合成有用的产率轻松获得四氢哒嗪衍生物。该反应条件温和，官能团耐受性良好。此外，在DDQ存在下，所得产物可以很容易地转化为哒嗪-3-酮衍生物。
• 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.