17396-36-0

Usage

Uses

Used in Culinary Industry:
Thian-4-one S-oxide is used as a flavor and aroma enhancer in various culinary dishes, contributing to the unique taste and smell of Allium species.
Used in Chemical Defense Mechanisms:
Thian-4-one S-oxide plays an important role in the chemical defense mechanisms of Allium plants, as it can cause eye irritation and tearing when onions are chopped, reacting with the moisture in the eyes to form sulfuric acid.

InChI:InChI=1/C5H8O2S/c6-5-1-3-8(7)4-2-5/h1-4H2

Upstream product

• 1072-72-6 Tetrahydrothiopyran-4-one 
• 4131-74-2 Dimethyl 3,3'-thiodipropionate 
• 4160-61-6 3-methoxycarbonyltetrahydropyran-4-one 

Downstream Products

• 1072-72-6 Tetrahydrothiopyran-4-one 
• 57242-69-0 2,3-dihydro-4H-thiopyran-4-one 
• 137423-32-6 trans-7-(Phenylselenenyl)-1,4-dioxa-8-thiaspiro<4.5>decane 8-oxide 

Relevant academic research and scientific papers

1,2-dipyridiniumditribromide-ethane (DPTBE) as a new oxidizing agent for the chemoselective oxidation of sulfides to the sulfoxides

A wide range of aliphatic or aromatic sulfides is selectively oxidized to the corresponding sulfoxides using 1,2-dipyridiniumditribromide-ethane (DPTBE) in a mixture of CH2Cl2/H2O under heterogeneous conditions in moderate to high yields. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

Microwave thermolysis with clayfen: Solvent-free oxidation of sulfides to sulfoxides

Alkyl, aryl and cyclic sulfides are rapidly oxidized to the corresponding sulfoxides in high yields upon microwave thermolysis with iron(III) nitrate impregnated on clay (clayfen) under solvent-free conditions; the conversion also occurs in refluxing methylene chloride but requires much longer reaction time.

Carbazole-triazine based donor-acceptor porous organic frameworks for efficient visible-light photocatalytic aerobic oxidation reactions

We report the synthesis of a series of carbazole-triazine based donor-acceptor (D-A) POFs and their photocatalytic activities for aerobic oxidation reactions. The simultaneous introduction of a carbazole-based electron donor and a triazine-based electron acceptor in D-A POFs stabilizes the charge transfer state and enables an efficient triplet-triplet energy transfer to generate 1O2. Meanwhile, systematic variation of the D-A distance results in the tunable photoredox properties and consequently the efficiency for generation of reactive oxygen species (ROSs). Upon visible light excitation, all three D-A POFs exhibit excellent capability to promote three aerobic oxidations: sulfide oxidation, oxidative amine coupling, and Mannich reactions. This systematic study validates the design principle of D-A POFs as high-performance photo-oxidation catalysts with wide substrate scope and excellent stability and recyclability.

Synthesis and characterization of sulfide, sulfoxide and sulfone derivatives of thiopyran: antimicrobial evaluation

Abstract: A series of thiopyran derivatives and their oxidized analogous forms were synthesized and characterized by FT-IR, 1H, 13C, 31P NMR and mass spectroscopy techniques. The antibacterial and antifungal activities of these synthesized materials were evaluated against Staphylococcus aureus and Bacillus subtilis, as Gram-positive bacteria, and Escherichia coli and Pseudomonas aeruginosa, as Gram-negative bacteria, as well as the fungus Candida albicans. The results revealed that thiopyran S,S-dioxides are the most effective against all the bacteria studied in this work. Furthermore, thiopyran S-oxides showed excellent antifungal activity against Candida albicans.

Manganese- and Lanthanide-Based 1D Chiral Coordination Polymers as an Enantioselective Catalyst for Sulfoxidation

The chiral 1D-coordination polymers (CP) {[Ln2(MnLCl)2(NO3)2(dmf)6(H2O)2]·xH2O}n [Ln = Pr (1), Nd (2), Sm (3), and Gd (4)] were synthesized by the reaction of N,N'-bis(4-carboxysalicylidene)cyclohexanediamine (H4L) with [MnCl2·4(H2O)] and [Ln(NO3)3·x(H2O)] in the presence of dmf/pyridine at 90 °C. The polymers consist of manganese-salen-based moieties having carboxylate linkers connected to rare earth atoms in a 1D-chain structure. The polymers are very easily accessible. A one-step synthesis for the ligand and a second step for the preparation of the 1D coordination polymers starting from commercially available material are needed. The solid state structures of 1-4 were established by single-crystal X-ray diffraction. Compounds 1-4 were investigated as heterogeneous catalysts for the sulfoxidation reaction of various alkyl and aryl sulfides. The influence of various solvents and oxidizing agents on the catalytic reaction was examined. It was found that the catalysts were active for more than one reaction cycle without significant loss of activity. For phenylsulfide with 1 mol % of the catalyst 4, a maximum conversion 100% and a chemoselectivity 88% were observed.

Polyoxomolybdate-Calix[4]arene Hybrid: A Catalyst for Sulfoxidation Reactions with Hydrogen Peroxide

An easily accessible polyoxomolybdate-calix[4]arene hybrid 1 has been synthesized and applied as a heterogeneous catalyst in the sulfoxidation of thioethers to sulfoxides and to sulfones under strictly stoichiometric amounts of 30% H2O2 in CH3CN as the solvent. This study represents the first promising example of successful employment of calixarenes-polyoxometalate (POM) hybrid materials in the area of catalytic oxidations.

127. Reactions of sulfinylated radicals. Stereoselectivity in six-membered rings

The allylation and deuteration of six-membered cyclic sulfinylated radicals were investigated. For this purpose, radicals with the predefined conformations I and I1 were generated from 2-(phenylselenenyl)thiacyclohexane-1-oxide derivatives 7-10 (Scheme).

Ammonium salt catalyzed oxidation of organosulfides to organosulfoxydes

The selective oxidation of aromatic and aliphatic organosulfides with H2O2/H2O catalyzed by metal free ammonium salts has been explored. Reactions were performed using 2.5-5 mol % of catalyst loadings, isolating the corres

Hydrogenation of sulfoxides to sulfides under mild conditions using ruthenium nanoparticle catalysts

The first demonstration of the hydrogenation of sulfoxides under atmospheric H2 pressure is reported. The highly efficient reaction is facilitated by a heterogeneous Ru nanoparticle catalyst. The mild reaction conditions enable the selective hydrogenation of a wide range of functionalized sulfoxides to the corresponding sulfides. The high redox ability of RuO x nanoparticles plays a key role in the hydrogenation.

Facile control of the charge density and photocatalytic activity of an anionic indium porphyrin framework via in situ metalation

An anionic indium porphyrin framework (UNLPF-10) consisting of rare Williams β-tetrakaidecahedral cages was constructed using an octatopic ligand linked with 4-connected [In(COO)4]- SBUs. Remarkably, the extent of indium metalation of porphyrin macrocycles in UNLPF-10 can be facilely tuned in situ depending on the M/L ratio during synthesis, resulting in a controllable framework charge density and photocatalytic activity toward the selective oxygenation of sulfides.