16212-06-9

Usage

Uses

Phenyl trans-beta-styryl sulfone is used as a building block for proteomics research.

Synthesis Reference(s)

Synthetic Communications, 19, p. 2209, 1989 DOI: 10.1080/00397918908052616Tetrahedron Letters, 25, p. 3203, 1984 DOI: 10.1016/S0040-4039(01)91008-1

InChI:InChI=1/C14H12O2S/c15-17(16,14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H/b12-11-

Upstream product

• 51755-92-1 β-phenyl-β-hydroxyethyl phenyl sulfone 
• 52147-97-4 trans 2-phenylethenesulfonyl chloride 
• 100-42-5 styrene 
• 873-55-2 sodium benzenesulfonate 
• 67-56-1 methanol 
• 32291-77-3 phenyl (Z)-β-styryl sulphone 
• 27846-25-9 1-phenyl-2-(phenylsulfonyl)ethane 
• 64-17-5 ethanol 
• 6461-58-1 (1-chloro-2-(phenylsulfonyl)ethyl)benzene 
• 4110-77-4 (E)-β-chlorostyrene 
• 100-34-5 benzene diazonium chloride 
• 2643-39-2 1-Benzenesulphonyl-2-bromo-2-phenylethane 
• 17872-92-3 (phenylsulfonylmethyl)trimethylsilane 
• 108-24-7 acetic anhydride 

Downstream Products

• 69333-48-8 1-phenyl sulphonyl-2-methoxy-2-phenyl ethane 
• 27846-25-9 1-phenyl-2-(phenylsulfonyl)ethane 
• 65885-18-9 phenyl (2-phenyl-2-ethoxy ethyl)sulphone 
• 21309-15-9 trans-2-phenyl-phenylsulfonyl cyclopropane 
• 55930-68-2 2-(1-Phenylsulfonyl-2-phenylaethyl)cyclohexanon 
• 344564-13-2 2-(1-Phenyl-2-phenylsulfonylaethyl)cyclohexanon 
• 82884-24-0 3-Benzenesulfonyl-2,6-diphenyl-2,3,4,7-tetrahydro-1H-azepine 
• 16037-44-8 4-phenyl-3-trimethylsilylpyrazole 
• 3846-66-0 (E)-1-tert-butyl-2-phenylethene 
• 3846-66-0 β-tert-butylstyrene 
• 113303-16-5 3,3-dimethyl-2-phenylbutyl phenyl sulfone 
• 3740-05-4 (Z)-1-(3,3-dimethylbut-1-enyl)benzene 
• 117917-66-5 C₂₂H₂₃⁽²⁾HO₂SSi 
• 117917-66-5 C₂₂H₂₃⁽²⁾HO₂SSi 

Relevant academic research and scientific papers

ORGANIC SYNTHESIS WITH SULFONES XXXII. A CONVENIENT ROUTE TO α,β-UNSATURATED SULFONES FROM SATURATED SULFONE

α-sulfonyl lithiated anions are oxidized by cupric carboxylates into α,β-unsaturated sulfones.Primary sulfones lead to pure trans-vinylic sulfones.

Facile method for solid-phase synthesis of vinyl sulfones using polystyrene-supported selenomethyl aryl sulfone

Treatment of novel polystyrene-supported selenomethyl aryl sulfone with LDA followed by alkylation and oxidation elimination efficiently afforded vinyl sulfones in good yields and purities.

Controlled Synthesis of β-Keto Sulfones and Vinyl Sulfones under Electrochemical Oxidation

Selective sulfonylation and oxosulfonylation of alkenes with sulfinates have been developed via anodic oxidation in an undivided cell. The novel electrosynthetic method provided β-keto sulfones and vinyl sulfones with good to excellent yields in the absence of any transition metal catalyst and oxidants. Mechanism studies show that two different pathways involved in these two transformations.

Visible-Light-Induced Three-Component Intermolecular Trifluoromethyl-Alkenylation Reactions of Unactivated Alkenes

Herein, we describe a practical protocol for efficient, mild, visible-light-induced three-component intermolecular trifluoromethyl-alkenylation reactions of unactivated alkenes. The protocol has good functional group tolerance and a broad substrate scope. Using this protocol, we not only introduced a trifluoromethyl group into alkenes but also converted unactivated alkenes to styrene-based activated alkenes, in addition to accomplishing late-stage functionalization of pharmaceutical intermediates. (Figure presented.).

Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator

Herein we report a protocol for the direct visible-light-mediated alkenylation of alkyl boronic acids at room temperature without an external Lewis base as an activator, and we propose a mechanism involving benzenesulfinate activation of the alkyl boronic acids. The protocol permits the efficient functionalization of a broad range of cyclic and acyclic primary and secondary alkyl boronic acids with various alkenyl sulfones. We demonstrated its utility by preparing or functionalizing several pharmaceuticals and natural products.

Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide

A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.

Generation of potent Nrf2 activators via tuning the electrophilicity and steric hindrance of vinyl sulfones for neuroprotection

Oxidative stress is constantly involved in the etiopathogenesis of an ever-widening range of neurodegenerative diseases. As a consequence, effective repression of cellular oxidative stress to a redox homeostatic condition is a promising and feasible strategy to treat, or at least retard the progression of, such disorders. Nrf2, a primary orchestrator of cellular antioxidant response machine, is responsible for detoxifying and compensating for deleterious oxidative stress via transcriptional activation of a diverse array of antioxidant biomolecules. In the framework of our persistent interest in disclosing small molecules that interfere with cellular redox-regulating machinery, we report herein the synthesis, optimization, and biological assessment of 47 vinyl sulfone scaffold-bearing small molecules, most of which exhibit robust neuroprotective effect against H2O2-mediated lesions to PC12 cells. After initial screening, the most potent neuroprotective compounds 9b and 9c with marginal cytotoxicity were selected for the follow-up studies. Our results demonstrate that their neuroprotective effects are attributed to the up-regulation of a panel of antioxidant genes and corresponding gene products. Further mechanistic studies indicate that Nrf2 is indispensable for the cellular performances of 9b and 9c, arising from the fact that silence of Nrf2 gene drastically nullifies their protective action. Taken together, 9b and 9c discovered in this work merit further development as neuroprotective candidates for the treatment of oxidative stress-mediated pathological conditions.

Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants

2-Aryl-1-sulfonyl-substituted cyclobutanes were prepared in an intermolecular [2 + 2] photocycloaddition from various α,β-unsaturated sulfones and olefins upon irradiation at λ = 300 nm (26 examples, 60-99% yield). Lewis acids catalyzed the [2 + 2] photocycloaddition of 2-benzimidazolyl styryl sulfones. At short wavelengths, the latter substrates underwent C-S bond cleavage but AlBr3 (5 mol %) allowed for an intermolecular reaction with 2,3-dimethyl-2-butene at longer wavelengths. A chiral-at-metal Lewis acid (2 mol %) facilitated an enantioselective reaction (up to 77% ee).

PhB(OH)2-Promoted Electrochemical Sulfuration-Formyloxylation of Styrenes and Selectfluor-Mediated Oxidation-Olefination

We report a PhB(OH)2-promoted electrochemical sulfuration-formyloxylation reaction of styrenes employing commercially available thiophenols/thiols as thiolating agents. Specifically, metal catalysts and external chemical oxidants are not needed in the reaction for the formation of β-formyloxy sulfides, and these sulfides can be further converted to (E)-vinyl sulfones via the Selectfluor-mediated oxidation-olefination. Notably, on the basis of this electrochemical oxidation strategy, β-hydroxy sulfide, β-formyloxy sulfoxide, β-formyloxy sulfone, and (E)-vinyl sulfoxide can also be easily prepared.

Vinyl sulfone synthesisviacopper-catalyzed three-component decarboxylative addition

The synthesis of vinyl sulfone derivativesviathe reaction of arylpropiolic acids, K2S2O5, and aryl boronic acids is reported. The CuBr2/1,10-phenanthroline catalytic system in the presence of acetic acid provide