(E)-butyl 3-tosylacrylate | 139450-10-5

• 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)-butyl 3-tosylacrylate
• 英文别名: butyl (E)-3-tosylacrylate；butyl (E)-3-(4-methylphenyl)sulfonylprop-2-enoate
• CAS: 139450-10-5
• 化学式: C₁₄H₁₈O₄S
• 分子量: 282.361
• InChiKey: YZVPXBSMLXUVCX-PKNBQFBNSA-N

物化性质

• 沸点：
  429.5±45.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙烯酸丁酯 、 对甲基苯磺酰甲基异腈 在 copper acetylacetonate 、 硫酸 、 碘 、 氧气 、 eosin Y disodium salt 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以70%的产率得到(E)-butyl 3-tosylacrylate
  参考文献：
  名称：

  可见光促进烯烃的磺酰化和磺酰基羰基化

  摘要：

  描述了可见光促进了容易获得的烯烃与TosMIC的磺酰化和磺酰基羰基化反应，以合成有价值的乙烯基砜和β-酮砜。提出了一种合理的激进参与机制。

  DOI：

  10.1016/j.tetlet.2020.152029

文献信息

• Revealing the metal-like behavior of iodine: an iodide-catalysed radical oxidative alkenylation
  作者：Shan Tang、Yong Wu、Wenqing Liao、Ruopeng Bai、Chao Liu、Aiwen Lei

  DOI：10.1039/c4cc00644e

  日期：——

  Catalytic HI elimination similar to the β-hydride elimination of transition metals was realized for the radical alkenylation of sulfonyl hydrazides.

  类似于过渡金属的β-氢化物消除反应，对磺酰基肼的自由基烯基化实现了催化HI消除反应。
• 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。
• Antibacterial activity evaluation of vinyl sulfones against global predominant methicillin-resistant Staphylococcus aureus USA300
  作者：Onanong Vorasin、Khanchyd Momphanao、Praewpan Katrun、Chutima Kuhakarn、Chutima Jiarpinitnun

  DOI：10.1016/j.bmcl.2022.128652

  日期：2022.5

  Number of antibacterial vinyl sulfone derivatives were discovered. Among these, nitrile-substituted vinyl phenyl sulfones showed potent antibacterial activity. (E)-3-((4-methoxyphenyl)sulfonyl)acrylonitrile exhibited the strongest potency with MIC of 1.875 µg/mL against methicillin susceptible S. aureus and 3.75 µg/mL against MRSA USA300. Based on the structure–activity relationship analysis, the antibacterial

  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
• 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.
• Visible light promoted sulfonylation and sulfonylcarbonylation of alkenes
  作者：Wenjian Min、Guozhe Guo、Caixia Yang、Congde Huo

  DOI：10.1016/j.tetlet.2020.152029

  日期：2020.6

  Visible light promoted sulfonylation and sulfonylcarbonylation reactions of readily available alkenes with TosMIC for the synthesis of valuable vinyl sulfones and β-keto sulfones were described. A reasonable radical involved mechanism is proposed.

  描述了可见光促进了容易获得的烯烃与TosMIC的磺酰化和磺酰基羰基化反应，以合成有价值的乙烯基砜和β-酮砜。提出了一种合理的激进参与机制。