(E)-2-methyl-3-tosylacrylonitrile | 1256465-77-6

• 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: (E)-2-methyl-3-tosylacrylonitrile
• 英文别名: (E)-2-methyl-3-(4-methylphenyl)sulfonylprop-2-enenitrile
• CAS: 1256465-77-6
• 化学式: C₁₁H₁₁NO₂S
• 分子量: 221.28
• InChiKey: IQDNXOXNCPLUDR-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  sodium 4-methylbenzenesulfinate 、 甲基丙烯腈 在 碘苯二乙酸 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以36%的产率得到(E)-2-methyl-3-tosylacrylonitrile
  参考文献：
  名称：

  乙烯基砜对全球主要耐甲氧西林金黄色葡萄球菌USA300的抗菌活性评价

  摘要：

  乙烯基砜的亲电势允许在生理条件下快速捕获含半胱氨酸的蛋白质。这些半胱氨酸蛋白酶在金黄色葡萄球菌( S. aureus ) 和全球健康威胁耐甲氧西林金黄色葡萄球菌的细菌存活和发病机制中发挥着至关重要的作用。(MRSA)。在这里，总共合成了 28 种乙烯基砜，并对包括全球流行的 MRSA PFGE 菌株 USA300 (SF8300) 在内的病原菌进行了药敏试验。发现了许多抗菌乙烯基砜衍生物。其中，腈取代的乙烯基苯基砜显示出有效的抗菌活性。(E)-3-((4-甲氧基苯基)磺酰基)丙烯腈对甲氧西林敏感的金黄色葡萄球菌表现出最强的效力，MIC 为 1.875 µg/mL和 3.75 µg/mL 针对 MRSA USA300。基于构效关系分析，这些化合物的抗菌活性可能涉及巯基共轭。此外，腈取代的乙烯基苯砜也可能损害宿主细胞的粘附。凭借其有希望的抗菌活性，这些乙烯基砜具有用于金黄色葡萄球菌和 MRSA

  DOI：

  10.1016/j.bmcl.2022.128652

文献信息

• PhI(OAc)2/KI-Mediated Reaction of Aryl Sulfinates with Alkenes, Alkynes, and α,β-Unsaturated Carbonyl Compounds: Synthesis of Vinyl Sulfones and β-Iodovinyl Sulfones
  作者：Praewpan Katrun、Supanimit Chiampanichayakul、Kanokwan Korworapan、Manat Pohmakotr、Vichai Reutrakul、Thaworn Jaipetch、Chutima Kuhakarn

  DOI：10.1002/ejoc.201000641

  日期：2010.10

  (Diacetoxyiodo)benzene [PhI(OAc) 2 , DIB] was able to promote the reaction of sodium aryl sulfinate and potassium iodide (KI) with alkenes and alkynes to afford the corresponding vinyl sulfones and β-iodovinyl sulfones, respectively, in good yields. The salient features of this reaction are that it employs a commercially available and environmentally benign hypervalent iodine(III) reagent, a one-step

  (二乙酰氧基碘)苯 [PhI(OAc) 2 , DIB] 能够促进芳基亚磺酸钠和碘化钾 (KI) 与烯烃和炔烃的反应，分别以良好的产率得到相应的乙烯基砜和 β-碘乙烯基砜. 该反应的显着特点是采用市售且环境友好的高价碘（III）试剂，一步反应，反应时间短，反应条件温和。
• An Improved Synthesis of Vinyl- and β-Iodovinyl Sulfones by a Molecular Iodine-Mediated One-Pot Iodosulfonation-Dehydroiodination Reaction
  作者：Tassaporn Sawangphon、Praewpan Katrun、Korbua Chaisiwamongkhol、Manat Pohmakotr、Vichai Reutrakul、Thaworn Jaipetch、Darunee Soorukram、Chutima Kuhakarn

  DOI：10.1080/00397911.2012.663448

  日期：2013.6.18

  An improved one-pot method to synthesize vinyl sulfones from unsaturated systems by using molecular iodine/sodium arenesulfinate/sodium acetate as reagents was described. Vinyl sulfones derived from styrene derivatives were generally obtained in good to excellent yields except for those bearing strong electron releasing substituent. Aliphatic alkenes and activated alkenes gave the corresponding vinyl sulfone products in moderate to good yields. Arylacetylenes yielded the respective -iodovinyl sulfones in good yields while low yield was observed with aliphatic terminal alkyne. The potentials of the method entail simplicity, short reaction time, non-anhydrous reaction conditions, employing inexpensive, non-metallic reagent and integrating two reactions that are commonly accomplished separately into a single operation.