2-((3-nitrophenyl)sulfonyl)-1-phenylethan-1-one | 41024-49-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((3-nitrophenyl)sulfonyl)-1-phenylethan-1-one
• 英文别名: 2-(3-nitrophenyl)sulfonyl-1-phenylethanone
• CAS: 41024-49-1
• 化学式: C₁₄H₁₁NO₅S
• 分子量: 305.311
• InChiKey: MIVOMOGHKPEYBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  94.35
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 bis(3-nitrophenyl)iodonium tetrafluoroborate 在 双(二氧化硫)-1,4-二氮杂双环[2.2.2]辛烷加合物 、 2,4,5,6-四(9H-咔唑-9-基)异酞腈 作用下， 以 1,4-二氧六环 为溶剂， 以53 %的产率得到2-((3-nitrophenyl)sulfonyl)-1-phenylethan-1-one
  参考文献：
  名称：

  Photoredox-catalyzed sulfonylation of diaryliodonium salts with DABSO and silyl enolates involving the insertion of SO2

  摘要：

  A versatile photoredox-catalyzed three-component sulfonylation of diaryliodonium salts with DABSO and silyl enolates involving the insertion of SO2 for the synthesis of β-keto sulfones was developed.

  DOI：

  10.1039/d4ra02773f

文献信息

• Oxidative Sulfonylation of Hydrazones Enabled by Synergistic Copper/Silver Catalysis
  作者：Jun Xu、Chao Shen、Xian Qin、Jie Wu、Pengfei Zhang、Xiaogang Liu

  DOI：10.1021/acs.joc.0c02249

  日期：2021.3.5

  A copper/silver-cocatalyzed protocol for oxidative sulfonylation of hydrazones is demonstrated. A wide range of β-ketosulfones and N-acylsulfonamides are directly synthesized in moderate to good yields. Our work provides a viable method for scalable preparation of β-ketosulfone derivatives that have found wide applications in the pharmaceutical industry.

  证明了铜/银共催化的sulf的氧化磺酰化方案。可以以中等到良好的产率直接合成各种各样的β-酮砜和N-酰基磺酰胺。我们的工作为在制药工业中发现了广泛应用的β-酮砜衍生物的可扩展制备提供了一种可行的方法。
• Visible-light-promoted oxidative difunctionalization of alkenes with sulfonyl chlorides to access β-keto sulfones under aerobic conditions
  作者：Teng-fei Niu、Jing Cheng、Chang-li Zhuo、Ding-yun Jiang、Xing-ge Shu、Bang-qing Ni

  DOI：10.1016/j.tetlet.2017.08.013

  日期：2017.9

  A mild, practical and efficient strategy to prepare β-keto sulfones has been developed by visible light promoted reactions. This reaction involves Ir(ppy)2(dtbbpy)PF6 catalyzed direct funcationalization of alkenes with sulfonyl chlorides under mild conditions. Air was used as oxidant without any additives. The transformation affords the corresponding products in moderate to high yields.

  通过可见光促进的反应，已经开发出一种温和，实用和有效的制备β-酮砜的策略。该反应涉及在温和的条件下，Ir（ppy）2（dtbbpy）PF 6催化的烯烃与磺酰氯的直接官能化反应。空气被用作氧化剂，没有任何添加剂。该转化以中等至高产率提供了相应的产物。
• Heterogeneous Carbon Nitrides Photocatalysis Multicomponent Hydrosulfonylation of Alkynes To Access β-Keto Sulfones with the Insertion of Sulfur Dioxide in Aerobic Aqueous Medium
  作者：Bangqing Ni、Binbin Zhang、Jine Han、Bohan Peng、Yuling Shan、Tengfei Niu

  DOI：10.1021/acs.orglett.9b04454

  日期：2020.1.17

  Although hydrosulfonylation of alkynes is an ideal process to generate β-keto sulfones, such an approach is rarely implemented. Here we reported a facile and efficient graphitic carbon nitride (p-g-C3N4) photocatalyzed hydrosulfonylation of alkynes with the insertion of sulfur dioxide in aerobic conditions. Controlled experiments and ESR results indicated both the superoxide radicals and valence band

  尽管炔烃的氢磺酰化是生成β-酮砜的理想方法，但这种方法很少采用。在这里，我们报道了一种在有氧条件下插入二氧化硫的简便有效的石墨碳氮化碳（pg-C3N4）光催化炔烃的加氢磺酰化反应。对照实验和ESR结果表明，超氧自由基和价带孔均在反应中起重要作用。进一步的同位素实验证实了产物的氧原子来自H2O，而O2通过淬灭DABCO自由基阳离子在反应中起重要作用。无金属的异质半导体可完全回收至少6次，而没有明显的还原活性。此外，
• Visible-light-induced direct oxysulfonylation of alkynes with sulfonyl chlorides and HCl
  作者：Tengfei Niu、Dingyun Jiang、Bangqing Ni

  DOI：10.1016/j.tetlet.2017.09.083

  日期：2017.11

  efficient strategy to prepare β-keto sulfones has been developed by visible-light-induced reactions. This reaction involved Ir(dtbbpy)(ppy)2PF6-catalyzed direct functionalization of alkynes with sulfonyl chloride and HCl using air as the oxidant. HCl not only acted as a hydrogen source in the proton transfer process, but also played a vital role in the reaction process.

  通过可见光诱导的反应，已经开发出一种温和，实用，有效的制备β-酮砜的策略。该反应涉及Ir（dtbbpy）（ppy）2 PF 6催化的炔烃用磺酰氯和HCl的直接作用，以空气为氧化剂。HCl不仅在质子转移过程中充当氢源，而且在反应过程中也起着至关重要的作用。