64050-18-6

Upstream product

• 5941-55-9 ethyl 3-ethoxyacrylate 
• 108-98-5 thiophenol 
• 5459-35-8 2-bromo-acrylic acid ethyl ester 
• 31930-36-6 ethyl (E)-3-iodopropenoate 
• 140-88-5 ethyl acrylate 
• 31930-36-6 ethyl (Z)-3-iodopropenoate 
• 623-47-2 propynoic acid ethyl ester 
• 882-33-7 diphenyldisulfane 
• 116074-63-6 [((E)-Hex-2-enyl)sulfanyl]-benzene 
• 60805-64-3 ethyl 3-(phenylthio)propionate 
• 105-37-3 Ethyl propionate 
• 3674-13-3 2,3-dibromopropionic acid ethyl ester 
• 583-60-8 2-Methylcyclohexanone 

Downstream Products

• 711-29-5 3-phenylsulfonyl-2(Z)-propenoic acid 

Relevant academic research and scientific papers

Gold-Catalyzed Asymmetric Thioallylation of Propiolates via Charge-Induced Thio-Claisen Rearrangement

A gold(I)-catalyzed enantioselective thioallylation of propiolates with allyl sulfides is described. The key mechanistic element is a sulfonium-induced Claisen rearrangement which helps minimize the allyl dissociation and render higher enantioselectivity. This protocol features remarkable scope of the allyl moiety, allowing enantiocontrolled synthesis of all-carbon quaternary centers, and exhibits exceptional functional group compatibility with many Lewis bases and π-bonds. This intermolecular variant of Claisen rearrangement forges both C-S and C-C bonds concomitantly, providing efficient access to interesting optically active organosulfur compounds which can be transformed further through the vinyl sulfide as a functional handle. The rate of the reaction was zeroth order with respect to allyl sulfides, which suggested a reversible inhibition, providing a resting state for the catalyst. The Hammett plot displayed a correlation with σp values, suggesting a turnover-limiting sigmatropic rearrangement where decreased electron-density on sulfur accelerated the rearrangement.

Design and Synthesis of Novel 4-Phenoxyquinolines Bearing 3-Hydrosulfonylacrylamido or 1H-Imidazole-4-carboxamido Scaffolds as c-Met Kinase Inhibitors

A series of novel 6,7-disubstituted-4-phenoxyquinoline derivatives bearing (E)-3-hydrosulfonylacrylamido or 1H-imidazole-4-carboxamido moieties were designed, synthesized and evaluated for their cytotoxicity against A549, MKN-45, and HT-29 cancer cell lines in vitro. All the target compounds showed moderate to significant cytotoxic activity against the tested cells with IC50 values ranging from 0.13 to 2.65 μM. Five of them were further examined for their inhibitory activity against c-Met kinase, which identified compound 30 as a promising agent (c-Met IC50 = 1.52 nM) with IC50 values of 0.24, 0.45, and 0.13 μM against HT-29, MKN-45, and A549 cells, respectively.

Air Oxidative Radical Oxysulfurization of Alkynes Leading to α-Thioaldehydes

Air oxidative radical oxysulfurization of alkynes initiated by 0.5 mol % tert-butyl hydroperoxide with arylthiols is described. The reaction proceeded at room temperature in the presence of 5% mol water to afford selective α-thioaldehydes. (Chemical Equation Presented).

Organylzinc chalcogenolate promoted michael-type addition of α,β-unsaturated carbonyl compounds

We present the chemo-, regio-, and stereoselective synthesis of vinyl chalcogenide compounds promoted by organylzinc chalcogenolates. In this protocol, reductive cleavage of diorganyl dichalcogenide bonds by the Zn/NH 4OH system led to organylz

A recyclable biphasic system for stereoselective and easily handled hydrochalcogenations

Vinyl selenides and vinyl sulfides were prepared by hydrochalcogenation of alkynes with selenols and thiols generated in situ by the reduction of the corresponding diselenides and disulfides with elemental zinc in a biphasic acidic medium. The yields, ste

Organylzinc Chalcogenolate Promoted Michael-Type Addition of α,β-Unsaturated Carbonyl Compounds

We present the chemo-, regio-, and stereoselective synthesis of vinyl chalcogenide compounds promoted by organylzinc chalcogenolates. In this protocol, reductive cleavage of diorganyl dichalcogenide bonds by the Zn/NH4OH system led to organylzi

Selectivity reversal during thia-Michael additions using tetrabutylammonium hydroxide: Operationally simple and extremely high turnover

The use of tetrabutylammonium hydroxide as a novel and exceedingly efficient thia-Michael addition catalyst is herein described. This extremely simple methodology allows for the conjugate addition of a wide variety of mercaptan nucleophiles, and functions remarkably well with a very wide range of both classical and non-classical Michael acceptors. Contradistinctive to current literature reports, the use of this catalyst more efficiently promotes the addition of more basic thiols. This methodology is especially attractive and operationally simple, as it generally proceeds with only 1 mol% catalytic loading and without excess reagent, and the produced products typically require no purification. Georg Thieme Verlag Stuttgart New York.

One-pot three-step thioconjugate addition-oxidation-Diels-Alder reactions of ethyl propiolate

Ethyl propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels-Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S-aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47% to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step-by-step.

One-pot synthesis of (Z)-β-sulfonyl enoates from ethyl propiolate

β-Sulfonyl enoates may be synthesized through a one-pot two-step sequence from ethyl propiolate with good to excellent selectivity for the Z isomer. Trialkylamines catalyze thioconjugate additions of aryl thiols, and alkoxides catalyze the addition of ali

A green and rapid approach for the stereoselective vinylation of phenol, thiol and amine derivatives in water

The stereoselective formation of C-O, C-S and C-N bonds by the reaction of phenols, thiols and amines with activated alkynes is described. The reactions are successfully conducted in water with excellent yields at room temperature. The lack of organic sol