17577-21-8

Upstream product

• 201230-82-2 carbon monoxide 
• 780-25-6 N-benzylidene benzylamine 
• 106-45-6 para-thiocresol 
• 622-29-7 N-Benzylidenemethylamine 
• 874-60-2 4-methyl-benzoyl chloride 
• 100-53-8 phenylmethanethiol 
• 104-87-0 4-methyl-benzaldehyde 
• 100-44-7 benzyl chloride 
• 150-60-7 dibenzyl disulphide 
• 13222-85-0 p-methylbenzoic anhydride 
• 6313-36-6 benzyl thiosulphate 
• 99-94-5 p-Toluic acid 
• 874-58-8 4-methylbenzoyl bromide 
• 16601-02-8 S-benzyl 4-methylbenzenethiosulfonate 

Downstream Products

• 1173163-85-3 C₂₃H₂₈OS 

Relevant academic research and scientific papers

Synthesis of thiol esters using nano CuO/Ionic liquid as an eco-friendly reductive system under microwave irradiation

We report an efficient, fast, and environmentally friendly method for the synthesis of a wide range of thiol esters using stable diorganoyl disulfides and acyl chlorides, using CuO nanoparticles and [pmim]Br as the reductive system. This method gave good to excellent isolated yields of the desired products after only three minutes of microwave irradiation. Furthermore, by using the same green approach, we were also able to synthesize thiocarbonates bearing interesting functionalities. We report an efficient, fast, and environmentally friendly method for the synthesis of thiol esters starting from diorganoyl disulfides and acyl chlorides, and using CuO nanoparticles and [pmim]Br as the reductive system. This approach gave good to excellent isolated yields of the desired products in only three minutes under microwave irradiation. Copyright

Preparation method of alkyne amide mediated thioester compound

The invention discloses a brand-new thioester compound preparation method, which comprises the following steps of: using a carboxylic acid compound as a raw material and an alkyne amide compound as acondensing agent, carrying out stirring reaction in an aprotic solvent to obtain an alpha-acyloxy alkenyl amide compound, and then reacting the alpha-acyloxy alkenyl amide compound with a thiol or thiophenol compound to obtain the target thioester compound under the catalysis of alkali. Or the two steps of reactions can be carried out by a one-pot method, i.e., an intermediate generated after thereaction of the carboxylic acid compound and the alkyne amide compound does not need to be separated, and the thiol or thiophenol compound is directly added to carry out the next step of reaction after the solvent is removed, so that the synthesis of the alkyne amide mediated thioester compound can be realized under mild conditions. The synthesis method provided by the invention is mild in condition and simple to operate, has no racemization phenomenon for carboxylic acid compounds with chirality at the carboxyl alpha position no matter generating active intermediates or forming thioester bonds, and has wide industrial application prospects.

Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light

A metal- and oxidant-free catalytic method for accessing structurally diverse thioesters from readily accessible, widespread aldehydes, is described. A strategy of a simple organic 9,10-phenanthrenequinone-promoted hydrogen atom transfer (HAT) with visible light was successfully implemented to selectively generate acyl radicals without inducing crossover reactivity of thioester products. The preparative power of the method was demonstrated by broad substrate scope and wide functional group tolerance, and enabled the late-stage modification of complex structures, which are difficult to achieve with the existing protocols.

Aerobic oxidative esterification and thioesterification of aldehydes using dibromoisocyanuric acid under mild conditions: No metal catalysts required

A practical direct method for the direct preparation of esters and thioesters from aldehydes is described. Esters and thioesters were synthesized by oxidative esterification and thioesterification via in situ generated acyl bromide intermediates, which were used to react with various alcohols and thiols. The esterification and thioesterification were readily performed in the presence of dibromoisocyanuric acid in dichloromethane, without any metal catalysts and under mild conditions. By using this reaction protocol, various esters and thioesters were prepared in high yields. This effective method offers a promising approach for the facile esterification and thioesterification of aldehydes.

Microwave-assisted direct thioesterification of carboxylic acids

A one-pot synthesis of thioesters directly from carboxylic acids, N,N′-diphenylthiourea, triethylamine, and primary alkyl halides is described. Microwave-assisted heating and a catalytic amount of 4- (dimethylamino)pyridine (DMAP) further improved the yields. Both aromatic and aliphatic carboxylic acids were converted to the corresponding thioesters, and many functional groups were compatible with this reaction. Several possible reaction intermediates were investigated, and the quaternary ammonium salts, derived from alkyl halides and tertiary amines, were the intermediates to yield thioesters. A new reaction mechanism for this thioesterification is proposed.

One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea

An efficient and odourless procedure for a one-pot synthesis of thioesters by the reaction of benzoic anhydrides, thiourea and various organic halides (primary, allylic, and benzylic) or structurally diverse, electron-deficient alkenes (ketones, esters, and nitriles) in the presence of Et3 N has been developed. In this method, thiobenzoic acids were in situ generated from the reaction of thiourea with benzoic anhydrides, which were subjected to conjugate addition with electron-deficient alkenes or a nucleophilic displacement reaction with alkyl halides.

An odorless, one-pot synthesis of thioesters from organic halides, thiourea and benzoyl chlorides in water

Thioesterification can be realized via an odorless, one-pot reaction through the in situ generation of S-alkylisothiouronium salts from organic halides and thiourea in aqueous Triton X-100 (TX100) micelles. The protocol is free of foul-smell thiols and or

NHC-catalyzed thioesterification of aldehydes by external redox activation

The NHC-catalyzed thioesterification of aromatic or aliphatic aldehydes with a range of thiols was developed in the presence of a stoichiometric amount of an organic oxidant. Among the oxidants examined, phenazine was shown to give the best results in terms of chemical yield and compatibility with thiols.

Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A2: Synthesis, spectroscopic and computational studies

4-Chlorothiobenzoic acid S-benzyl ester (I), 3-nitrothiobenzoic acid S-benzyl ester (II), 4-nitrothiobenzoic acid S-benzyl ester (III) and 4-methylthiobenzoic acid S-benzyl ester (IV) were prepared and characterized by 1H and 13C NMR, Mass spectrometry and IR spectroscopy. Quantum chemical calculations were performed with Gaussian 09 to calculate the geometric parameters and vibrational spectra. Phospholipase A2 (PLA2) was purified from Crotalus durissus cumanensis venom by molecular exclusion chromatography, followed by reverse phase-high performance liquid chromatography. Two studies of the inhibition of phospholipase A 2 activity were performed using phosphatidilcholine and 4-nitro-3-octanoyloxybenzoic acid as substrates, in both cases compound II showed the best inhibitory ability, with 74.89% and 69.91% of inhibition, respectively. Average percentage of inhibition was 52.49%. Molecular docking was carried out with Autodock Vina using as ligands the minimized structures of compounds (I-IV) and as protein PLA2 (PDB code 2QOG). The results suggest that compounds I-IV could interact with His48 at the active site of PLA2. In addition, all compounds showed Van der Waals interactions with residues from hydrophobic channel of the enzyme. This interaction would impede normal catalysis cycle of the PLA2.