28975-80-6

Usage

Uses

Used in Organic Synthesis:
(prop-1-en-1-ylsulfonyl)benzene is used as a building block for the preparation of various chemicals and materials. Its strong nucleophilic reactivity, attributed to the electron-withdrawing sulfonyl group, makes it a versatile reagent in a wide array of chemical reactions.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, (prop-1-en-1-ylsulfonyl)benzene is studied for its potential biological and pharmacological activities. It has shown promise as an antifungal agent, which could lead to the development of new treatments for fungal infections.
Used in Materials Science:
(prop-1-en-1-ylsulfonyl)benzene's unique properties also make it a candidate for use in materials science, where it could contribute to the development of novel materials with specific characteristics, such as enhanced reactivity or stability.

Upstream product

• 16212-05-8 (allylsulfonyl)benzene 
• 937-41-7 phenyl acrylate 
• 107-13-1 acrylonitrile 
• 873-55-2 sodium benzenesulfonate 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 106-95-6 allyl bromide 
• 75-56-9 methyloxirane 
• 1202639-02-8 C₂₂H₂₆N₄O₁₀S 
• 141-05-9 Diethyl maleate 
• 623-91-6 diethyl Fumarate 
• 292638-85-8 acrylic acid methyl ester 
• 78-94-4 methyl vinyl ketone 
• 17872-92-3 (phenylsulfonylmethyl)trimethylsilane 
• 75-07-0 acetaldehyde 

Downstream Products

• 29290-72-0 C₁₅H₁₆O₂S₂ 
• 54476-11-8 2-((3s,5s,7s)-adamantan-1-ylthio)pyridine 
• 103850-58-4 2-(adamant-1-yl)-1-phenylsulphonyl-1-(pyridine-2-thiyl) propane 
• 68276-72-2 1-(phenylsulfonyl)-2-propanol 
• 66536-75-2 (S)-(+)-1-(phenylsulfonyl)propan-2-ol 
• 102838-84-6 (R)-1-(phenylsulphonyl)propan-2-ol 
• 65210-93-7 (1,2-Dibromo-propane-1-sulfonyl)-benzene 
• 54897-43-7 (Z)-1-bromo-1-phenylsulphonylprop-1-ene 
• 1354643-07-4 2-methyl-1-(phenylsulfonyl)nonan-3-one 

Relevant academic research and scientific papers

Efficient electrocatalytic addition reactions of allyl phenyl sulfone to electron deficient alkenes

The use of tetraalkylammonium salts as electrolytes has been found to allow the formation of electrogenerated bases of especially high reactivity. Such conditions allow allyl phenyl sulfone to undergo addition to a variety of electron deficient vinyl and propenyl compounds (sulfone, ketone, nitrile, and ester). The additions are catalyzed by electrogenerated bases derived from the reactant itself, rather than via an added pro-base. The nature of the substrate molecule is seen to affect which type of product is formed, leading to an interplay between addition to 1 mol of substrate or to 2 mol of substrate. Yields of 1:1 adducts range from 6 to 81%, while yields of 1:2 adducts range from 57 to 96%.

An unprecedented stereoselective base-induced trimerization of an α-bromovinylsulfone

A unprecedented base-induced trimerization of bromovinylsulfone 1 afforded the cyclohexene 6 as a single diastereoisomer. Optimization of this reaction gave the adduct 6 in 49% yield. A mechanistic rationale for the trimerization involving consecutive SN2′ additions and [3,3]-rearrangements and a final stereoselective intramolecular conjugate addition is proposed and supported by M06-2X density functional theory calculations.

Synthesis of Sulfones and Sulfonamides via Sulfinate Anions: Revisiting the Utility of Thiosulfonates

Simple and high-yielding strategies for the production of a variety of sulfones and sulfonamides, using thiosulfonates synthesized by copper-catalyzed aerobic dimerization, are reported. Although thiosulfonates are an old class of compound, practical methods for their synthesis and utilization have not been rigorously developed. In this study, we revisit the reactions of easily accessible thiosulfonates to form sulfinate anions. Because of the similar reactivity of thiosulfonates and metal sulfinates derived from toxic SO2, thiosulfinates are proposed to be stable, nontoxic alternatives to metal sulfinate salts.

Rhodium-catalyzed asymmetric arylation of allyl sulfones under the conditions of isomerization into alkenyl sulfones

The reaction of 3-sulfolene with arylboronic acids in the presence of a chiral diene-rhodium catalyst under highly basic conditions (10 equiv of KOH) gave high yields of 3-arylsulfolanes with high enantioselectivity, where 3-sulfolene is in equilibration

A one-pot regioselective synthetic route to vinyl sulfones from terminal epoxides in aqueous media

A highly efficient LiBr catalysed regioselective synthesis of vinyl sulfones from readily available terminal epoxides and sodium sulfinates in a one-pot procedure using water as a reaction medium is reported. The protocol is adorned with several attributes of green chemistry like recycling of the catalyst, atom-economy and an aqueous medium.

CONTROLLED DRUG RELEASE FROM SOLID SUPPORTS

The invention relates to solid supports useful in medical applications that provide controlled release of drugs, such as peptides, nucleic acids and small molecules. The drugs are covalently coupled to the solid support through a linkage that releases the drug or a prodrug through controlled beta elimination.

CONTROLLED RELEASE FROM MACROMOLECULAR CONJUGATES

The invention relates to conjugates of macromolecular carriers and drugs comprising linkers that release the drug or a prodrug through rate-controlled beta-elimination, and methods of making and using the conjugates.

Synthesis of α- and β-Branched Ethers from Alcohols by Reaction of Acetals with Grignard Reagents: Synthesis of Isopropyl and Isobutyl Ethers of (1S*,2R*S*,4R*)-6-Methylenebicyclooctan-2-ol

Non-symmetrical acetals have been combined with Grignard reagents in toluene at reflux to generate α- and β-branched ethers in moderate to high yields.The synthesis of isopropyl and isobutyl ethers of the bicyclic alcohol 1 was accomplished using this methodology, although reactions in the syn-series were complicated by the formation of tricyclic products by an intramolecular cyclisation.The scope and limitations of the ether-forming reactions were explored with a series of acetals derived from primary, secondary and tertiary alcohols.The halide component of the Grignard reagent and the solvent were found to be an important factor in facilitating these reactions.

Decarboxylative radical addition to vinylsulphones and vinylphosphonium bromide: Some further novel transformations of geminal (pyridine-2-thiyl) phenylsulphones

Irradiation of O-acyl derivatives 1 of N-hydroxy-2-thiopyridone with visible light in the presence of phenyl vinyl sulphone or vinyl triphenylphosphonium bromide leads to the corresponding adducts 8 and 9 which can undergo a wide variety of further transformations.

Synthesis of Alkenes via Peterson Reaction

The α-phenylthiosilanes (2) have been used to prepare the α-silyl anions (1) by reaction with lithium naphthalenide; subsequent condensation with a carbonyl compound gave the alkene (8) via the Peterson reaction.The α-phenylthiosilanes (2) were prepared from n,n-bis(phenylthio)acetals (4) by reaction with lithium naphthalenide and chlorotrimethylsilane.The n,n-bis(phenylthio)acetals (4) were obtained, in turn, from 1,1-bis(phenylthio)acetals (5) by anion formation with butyl-lithium-N,N,N',N'-tetramethylethylenediamine complex in hexane followed by reaction with an alkyl halide.The Peterson reaction was also used to prepare vinyl sulphides (9) and vinyl sulphones (13).