Benzyl alkyl sulfoxides
Benzyl alkyl sulfoxides are a class of organosulfur compounds that feature a benzyl group attached to an alkyl sulfone moiety. These molecules exhibit diverse chemical properties due to the presence of both aromatic and aliphatic functionalities, making them valuable in various applications across pharmaceuticals, agrochemicals, and fine chemicals.
Structurally, these compounds contain a benzene ring substituted at one or more positions with alkyl groups, where each alkyl group is further connected via a sulfoxide moiety. The presence of the sulfoxide functional group introduces both electron-donating and -withdrawing properties, which can influence reactivity and solubility.
Benzyl alkyl sulfoxides are often employed in medicinal chemistry as potential drug candidates due to their ability to modulate enzyme activity, act as prodrugs, or serve as intermediates for the synthesis of more complex molecules. Additionally, they find applications in agrochemicals for enhancing pesticide efficacy and in fine chemicals for flavor and fragrance development.
These compounds are typically synthesized via sulfoxidation reactions, where an alkyl sulfide reacts with a peroxyacid under appropriate conditions to form the corresponding sulfoxide. The choice of substituents on both the benzene ring and the alkyl chain can significantly impact their biological activity and physical properties, allowing for tailored design for specific applications.
| Structure | Chemical Name | CAS | MF |
|---|---|---|---|
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2-CHLORO-5-(METHANESULFINYLMETHYL)BENZENE-1-SULFONYL CHLORIDE | 1343325-14-3 | C8H8Cl2O3S2 |
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2-(METHANESULFINYLMETHYL)BENZENE-1-SULFONYL CHLORIDE | 1566861-50-4 | C8H9ClO3S2 |
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1-(4-CHLOROPHENYL)-2-[(4-METHOXYBENZYL)SULFINYL]-1-ETHANONE O-METHYLOXIME | 320422-62-6 | C17H18ClNO3S |
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4-(benzylsulfinyl)butan-2-one | 88738-53-8 | C11H14O2S |
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3-(benzylsulfinyl)-L-alanine | 189082-77-7 | C10H13NO3S |
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Benzene, [[(1-methylethyl)sulfinyl]methyl]- | 33038-70-9 | C10H14OS |
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N-(2-Benzylsulfinylethyl)-6-chloropyridine-2-carboxamide | 1436125-25-5 | C15H15ClN2O2S |
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1-Bromo-4-(butylsulfinylmethyl)benzene | 1280786-57-3 | C11H15BrOS |
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Ralfuranone C; S-Me, S-oxide | 1638617-46-5 | C18H16O3S |
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4-(Mercaptomethyl)phenol; S-Me, S-oxide | 40289-25-6 | C8H10O2S |
Related Literature
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Christopher B. Rodell,Christopher B. Highley,Minna H. Chen,Neville N. Dusaj,Chao Wang,Lin Han,Jason A. Burdick Soft Matter, 2016,12, 7839-7847
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Matthew J. Gaunt,Jinquan Yu,Jonathan B. Spencer Chem. Commun., 2001, 1844-1845
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Gloria Belén Ramírez-Rodríguez,José Manuel Delgado-López,Jaime Gómez-Morales CrystEngComm, 2013,15, 2206-2212
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Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860
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Brindha J.,Balamurali M. M.,Kaushik Chanda RSC Adv., 2019,9, 34720-34734
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