43045-12-1

Usage

Structure

Carbon-nitrogen triple bond (thiocyanate group) and a ketone (oxo) group

Type of compound

Thiocyanate derivative with a chlorophenyl group and an oxoethyl moiety

Usage

As a chemical intermediate in the synthesis of various organic compounds and pharmaceuticals, in research and development, and in the production of specialty chemicals. (The exact properties and uses may vary depending on its specific application and formulation.)

Upstream product

• 1147550-11-5 ammonium thiocyanate 
• 99-02-5 3'-Chloroacetophenone 
• 41011-01-2 2-bromo-1-(3-chloro-phenyl)-ethanone 
• 333-20-0 potassium thioacyanate 
• 7677-24-9 trimethylsilyl cyanide 
• 2039-85-2 3-Chlorostyrene 

Downstream Products

• 1095051-68-5 C₉H₆ClNOS 
• 1569742-96-6 [3-(3,4-dimethoxyphenyl)thiophene-2,5-diyl]bis[(3-chlorophenyl)methanone] 
• 1569742-86-4 [3-(4-methoxyphenyl)thiophene-2,5-diyl]bis[(3-chlorophenyl)methanone] 
• 1569742-68-2 [3-(p-tolyl)thiophene-2,5-diyl]bis[(3-chlorophenyl)methanone] 

Relevant academic research and scientific papers

α-Selective C(sp3)-H Thio/Selenocyanation of Ketones with Elemental Chalcogen

A facile method is disclosed for the synthesis of α-thio/selenocyanato ketones through regioselective C-H thio/selenocyanation of ketones. The advantages include the use of easily available starting materials, high efficiency, simple operation, and easy scale-up. Control experiments provide evidence that the reaction proceeded via a radical way, while kinetic isotope effect experiments reveal that the cleavage of the C-H bond serves as the rate-limiting step.

Visible-light-promoted thiocyanation of sp2C-H bonds over heterogeneous graphitic carbon nitrides

Mesoporous graphitic carbon nitride (mpg-C3N4) has been developed as a metal-free heterogeneous photocatalyst for thiocyanation transformations. The reaction proceeds efficiently by utilizing air as a green oxidant under mild reaction conditions, which affords SCN-containing compounds in moderate to excellent yields. Meanwhile, the practicality of this protocol is further demonstrated by the reusability of the mpg-C3N4photocatalyst and the scaled-up reaction. Furthermore, detailed mechanistic studies clearly demonstrate the role of oxygen.

Visible-Light-Promoted Difunctionalization of Olefins Leading to α-Thiocyanato Ketones

A simple and convenient visible-light-induced difunctionalization of alkenes with ammonium thiocyanate and dioxygen has been developed at room temperature. A series of α-thiocyanato ketones could be easily and efficiently obtained in moderate to good yields through the formation of C-S and C=O bonds simply by using nontoxic and inexpensive Na 2 -Eosin Y as a photocatalyst.

A 2-thiocyano HYPNONE derivatives method for the preparation of

The invention discloses a method for preparing 2-sulfur cyano acetophenone derivatives. The method for preparing the 2-sulfur cyano acetophenone derivatives comprises the following steps: dissolving styrene derivatives and ammonium thiocyanate in a solvent, and reacting at 20-30 DEG C to obtain 2-sulfur cyano acetophenone derivatives. According to the method for preparing the 2-sulfur cyano acetophenone derivatives, the styrene derivatives are taken as starting materials; the raw materials are easily available and various in type; products prepared by the method have various in type, can be directly used and can also be used for other further reactions; meanwhile, the method is mild in reaction conditions and simple in reaction operation and post-processing process; an accelerant does not need to be added; the production process meets the green and chemical requirements, is relatively high in yield and is suitable for large-scale production.

Molecular oxygen induced free radical oxythiocyanation of styrenes leading to α-oxothiocyanates

A facile and efficient protocol of oxythiocyanation of styrenes with ammonium thiocyanate has been developed. The reaction proceeded at room temperature using oxygen as sole oxidant to afford the α-oxothiocyanates via radical pathway in moderate to good yields. This method is straightforward, green and cost-effective, requires no catalyst and additives.

Synthesis of ionic liquid-supported hypervalent iodine reagent and its application as a 'catch and release' reagent for α-substituted acetophenones

A novel imidazolium-based ionic liquid-supported hypervalent iodine reagent has been synthesized and employed for a 'catch and release' strategy with substituted acetophenones to generate various α-substituted acetophenones in good to excellent yields. The use of an ionic liquid-supported hypervalent iodine reagent avoids chromatographic separation for the purification of α-substituted acetophenones and thus makes the method greener.

Fragment-based drug discovery of 2-thiazolidinones as inhibitors of the histone reader BRD4 bromodomain

Recognizing acetyllysine of histone is a vital process of epigenetic regulation that is mediated by a protein module called bromodomain. To contribute novel scaffolds for developing into bromodomain inhibitors, we utilize a fragment-based drug discovery approach. By successively applying docking and X-ray crystallography, we were able to identify 9 fragment hits from diffracting more than 60 crystals. In the present work, we described four of them and carried out the integrated lead optimization for fragment 8, which bears a 2-thiazolidinone core. After several rounds of structure guided modifications, we assessed the druggability of 2-thiazolidinone by modulating in vitro pharmacokinetic studies and cellular activity assay. The results showed that two potent compounds of 2-thiazolidinones have good metabolic stability. Also, the cellular assay confirmed the activities of 2-thiazolidinones. Together, we hope the identified 2-thiazolidinone chemotype and other fragment hits described herein can stimulate researchers to develop more diversified bromodomain inhibitors.

Selectfluor: A novel and efficient reagent for the rapid α-thiocyanation of ketones

The direct α-thiocyanation of ketones with ammonium thiocyanate has been achieved using Selectfluor under mild and neutral conditions to produce α-ketothiocyanates, in excellent yields and with high selectivity.

3,8-DIAZA-BICYCLO[4.2.0]OCT-3-YL AMIDES

The present invention relates to 3,8-diaza-bicyclo[4.2.0]oct-3-yl amide derivatives of formula (I), wherein the relative configuration of the diazabicyclooctane moiety is cis; and wherein Ar1, and Ar2 are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as orexin receptor antagonists.

3,8-DIAZA-BICYCLO[4.2.0]OCT-8-YL AMIDES

The present invention relates to 3,8-diaza-bicyclo[4.2.0]oct-8-yl amide derivatives of formula (I) Formula (I) wherein the relative configuration of the diazabicyclooctane moiety is cis; and wherein Ar1, and Ar 2 are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as orexin receptor antagonists.