N-(4-(苯基磺酰基)苯基)乙酰胺 | 107920-73-0

• 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-(4-(苯基磺酰基)苯基)乙酰胺
• 英文名称: N-(4-(phenylsulfonyl)phenyl)acetamide
• 英文别名: N-[4-(benzenesulfonyl)phenyl]acetamide
• CAS: 107920-73-0
• 化学式: C₁₄H₁₃NO₃S
• 分子量: 275.328
• InChiKey: XDBAVBNLQIDXOY-UHFFFAOYSA-N

物化性质

• 熔点：
  195 °C(Solv: ethanol, 50% (64-17-5))
• 沸点：
  527.5±33.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-(苯基磺酰基)苯基)乙酰胺 在 盐酸 作用下， 生成 4-(苯基磺酰基)苯胺
  参考文献：
  名称：

  Knuesli, Gazzetta Chimica Italiana, 1949, vol. 79, p. 621,625

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基联苯砜 在 盐酸 、 tin(ll) chloride 作用下， 生成 N-(4-(苯基磺酰基)苯基)乙酰胺
  参考文献：
  名称：

  Ullmann; Pasdermadjian, Chemische Berichte, 1901, vol. 34, p. 1155

  摘要：

  DOI：

文献信息

• Regiospecific Cleavage of S–N Bonds in Sulfonyl Azides: Sulfonyl Donors
  作者：Zhiguo Zhang、Songnan Wang、Yong Zhang、Guisheng Zhang

  DOI：10.1021/acs.joc.8b03046

  日期：2019.4.5

  Sulfonyl azides have been widely used as sulfonamido, diazo, and azido donors, as well as all-nitrogen 1,3-dipoles donors in synthetic chemistry. Here, the sulfonyl azides were used as efficient sulfonyl donors, which is very unusual. Trifluoromethanesulfonic acid-induced formation of the sulfonyl cation reactive species from sulfonyl azides was developed and used for the first time to couple various

  磺酰叠氮化物已被广泛用作合成化学中的磺酰氨基，重氮和叠氮基供体，以及全氮1,3-偶极供体。在这里，磺酰叠氮化物被用作有效的磺酰供体，这是非常不寻常的。研究了三氟甲磺酸诱导的由磺酰叠氮化物形成的磺酰阳离子反应性物质，并首次用于偶联各种灭活的芳烃，从而在环境温度下制备砜。
• A Class of Amide Ligands Enable Cu-Catalyzed Coupling of (Hetero)aryl Halides with Sulfinic Acid Salts under Mild Conditions
  作者：Jinlong Zhao、Songtao Niu、Xi Jiang、Yongwen Jiang、Xiaojing Zhang、Tiemin Sun、Dawei Ma

  DOI：10.1021/acs.joc.8b00888

  日期：2018.6.15

  The amide derived from 4-hydroxy-l-proline and 2,6-dimethylaniline is a powerful ligand for Cu-catalyzed coupling of (hetero)aryl halides with sulfinic acid salts, allowing the formation of a wide range of (hetero)aryl sulfones from the corresponding (hetero)aryl halides at considerably low catalytic loadings. The coupling of (hetero)aryl iodides and sodium methanesulfinate proceeds at room temperature

  衍生自4-羟基-1-脯氨酸和2,6-二甲基苯胺的酰胺是Cu催化（杂）芳基卤化物与亚磺酸盐偶联的强配体，可形成各种（杂）芳基砜由相应的（杂）芳基卤化物以低的催化负载量得到。（杂）芳基碘化物和甲烷亚磺酸钠的偶联在室温下仅用0.5mol％的CuI和配体进行，代表了在低催化负载和室温下Cu催化的芳基化的第一个实例。
• Efficient synthesis of aliphatic sulfones by Mg mediated coupling reactions of sulfonyl chlorides and aliphatic halides
  作者：Ying Fu、Qin-Shan Xu、Quan-Zhou Li、Zhengyin Du、Ke-Hu Wang、Danfeng Huang、Yulai Hu

  DOI：10.1039/c7ob00251c

  日期：——

  Sulfonyl chlorides were reduced to anhydrous sulfinate salts with magnesium under sonication. These sulfinates were alkylated to sulfones with alkyl chlorides in the presence of catalytic sodium iodide under sonication. A variety of aliphatic sulfones was efficiently prepared by this one-pot two-step procedure.

  在超声处理下，磺酰氯与镁还原为无水亚磺酸盐。在催化的碘化钠存在下，在超声处理下，用烷基氯将这些亚磺酸盐烷基化为砜。通过这一一锅两步程序，可以有效地制备各种脂肪族砜。
• Synthesis of Aryl Sulfones via <scp>l</scp>-Proline-Promoted CuI-Catalyzed Coupling Reaction of Aryl Halides with Sulfinic Acid Salts
  作者：Wei Zhu、Dawei Ma

  DOI：10.1021/jo047758b

  日期：2005.4.1

  The CuI/l-proline sodium salt catalyzed coupling reaction of aryl halides with sulfinic acid salts readily occurs at 80−95 °C in DMSO to give the corresponding aryl sulfones in good to excellent yields. This process is well-tolerated by a wide range of functional groups including hydroxyl, amino, acetanilide, ketone, ester, and nitrile. Using this method, 4-phenylsulfonyl- and 4-methanesulfonyl-substituted

  CuI / 1-脯氨酸钠盐催化的芳基卤化物与亚磺酸盐的偶联反应在DMSO中于80-95°C容易发生，从而以良好或极好的收率得到相应的芳基砜。广泛的官能团（包括羟基，氨基，乙酰苯胺，酮，酯和腈）可以很好地耐受该过程。使用这种方法，制备了4-苯基磺酰基-和4-甲磺酰基取代的1-苯基丙氨酸衍生物。
• CuI catalyzed sulfonylation of organozinc reagents with sulfonyl halides
  作者：Ying Fu、Wenbo Zhu、Xingling Zhao、Helmut Hügel、Zhouqiang Wu、Yuhu Su、Zhengyin Du、Danfeng Huang、Yulai Hu

  DOI：10.1039/c4ob00638k

  日期：——

  In this study, a facile CuI catalyzed synthesis of sulfones involving a nucleophilic addition of functionalized organozinc reagents to organic sulfonyl chlorides is realized. This reaction proceeds efficiently at room temperature, giving rise to various functional group substituted sulfones, generally in moderate to high yields. The method provides a novel, simple, and promising strategy for functionalized

  在这项研究中，实现了一种简便的CuI催化的砜合成，其中涉及将官能化的有机锌试剂亲核加成到有机磺酰氯中。该反应在室温下有效进行，通常以中等至高产率产生各种官能团取代的砜。该方法为硫化学研究领域中的功能化砜合成提供了一种新颖，简单，有希望的策略。