145784-33-4

Upstream product

• 64-17-5 ethanol 
• 33185-97-6 (E)-4-(4'-chlorophenyl)-2-oxo-3-buteneoic acid 
• 75-03-6 ethyl iodide 
• 873-73-4 4-n-chlorophenylacetylene 
• 924-44-7 glyoxylic acid ethyl ester 
• 104-88-1 4-chlorobenzaldehyde 
• 623-47-2 propynoic acid ethyl ester 
• 16089-64-8 (Z)-1-(4-chlorophenyl)-N-methylmethanimine oxide 
• 127-17-3 2-oxo-propionic acid 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 148345-13-5 3-(4'-chlorophenyl)-5-ethoxycarbonyl-2-methyl-4-isoxazoline 
• 74-88-4 methyl iodide 

Downstream Products

• 118010-70-1 1,5-bis-(4-chlorophenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester 
• 1412191-43-5 (Z)-ethyl 4-(4-chlorophenyl)-2-((triethylsilyl)oxy)but-2-enoate 
• 1228363-14-1 (4R)-ethyl 4-(4-chlorophenyl)-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano[3,2-c]chromene-2-carboxylate 
• 1403685-45-9 (2S,3S,4R)-dimethyl 3-(2-ethoxy-2-oxoacetyl)-2-(4-chlorophenyl)-4-vinylcyclopentane-1,1-dicarboxylate 
• 1352576-59-0 diethyl 4-(4-chlorophenyl)-6-methyl-4H-pyran-2,5-dicarboxylate 
• 1352576-60-3 ethyl 4-(4-chlorophenyl)-6-(2-ethoxy-2-oxoethylidene)-4,5-dihydro-6H-pyran-2-carboxylate 
• 1233334-65-0 ethyl-4-(4-chlorophenyl)-2-hydroxy-7,7-dimethyl-5-oxo-3,4,5,6,7,8-hexahydro-2H-chromene-2-carboxylate 

Relevant academic research and scientific papers

CuBr-promoted formal hydroacylation of 1-alkynes with glyoxal derivatives: An unexpected synthesis of 1,2-dicarbonyl-3-enes

An efficient and concise protocol has been developed for the highly regio- and stereoselective synthesis of E-1,2-dicarbonyl-3-ene derivatives by a copper-promoted reaction of 1-alkynes with α-carbonyl aldehydes in the presence of morpholine. The products obtained are believed as the formal hydroacylation of the triple bond.

A mild method for indium(III)-catalyzed 1,4-hydrosilylation of α,β-enone esters with triethylsilane and trifluoroacetic acid

A chemo- and stereoselective 1,4-hydrosilylation of α,β-enone esters was developed using triethylsilane and trifluoroacetic acid under indium chloride catalysis. Georg Thieme Verlag Stuttgart ? New York.

Design and synthesis of 2,4-disubstituted polyhydroquinolines as prospective antihyperglycemic and lipid modulating agents

A series of 2,4-disubstituted polyhydroquinoline were synthesized and evaluated for their in vivo antihyperglycemic as well as antidyslipidemic activities. Several synthesized compounds have exhibited promising in vivo antihyperglycemic in SLM, STZ-S, and db/db mice model along with significant lipid and TG modulating activity. All these compounds were evaluated in various in vitro models of diabetes to know the possible mechanism of their antihyperglycemic action. Interestingly, compounds 3a-r (diaryl substitution) have exhibited promising protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity whereas, compounds 5a-d (acid substituted) have shown significant glycogen phosphorylase activity.

Highly enantioselective sequential hydrogenation of ethyl 2-Oxo-4-arylbut-3-enoate to ethyl 2-hydroxy-4-arylbutyrate

(Chemical Equation Presented) The hydrogenation of (E)-ethyl 2-oxo-4-arylbut-3-enoate with [NH2Me2]+[{RuCl [(S)-SunPhos]}2(μ-Cl3)] gave ethyl 2-hydroxy-4- arylbutyrate with 94-96% ee. Further investigation has proved that the hydrogenation proceeded via a sequential hydrogenation of C=O and C=C bonds, which is sensitive to the reaction temperature. Hydrolysis of ethyl 2-hydroxy-4-phenylbutyrate (ee 93%) provided the 2-hydroxy-4-phenylbutyric acid with 81% yield at 99% ee after a single recrystallization from 1, 2-dichloroethylene.

Diaryl dihydropyrazole-3-carboxamides with significant in vivo antiobesity activity related to CB1 receptor antagonism: Synthesis, biological evaluation, and molecular modeling in the homology model

A number of analogues of diaryl dihydropyrazole-3-carboxamides have been synthesized. Their activities were evaluated for appetite suppression and body weight reduction in animal models. Depending on the chemical modification of the selected dihydropyrazole scaffold, the lead compounds - the bisulfate salt of (±)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-1H-pyrazole-3- carboxylic acid morpholin-4-ylamide 26 and the bisulfate salt of (-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-1H-pyrazole-3- carboxylic acid morpholin-4-ylamide 30-showed significant body weight reduction in vivo, which is attributed to their CB1 antagonistic activity and exhibited a favorable pharmacokinetic profile. The molecular modeling studies also showed interactions of two isomers of (±)-5-(4-chlorophenyl)-1-(2,4- dichlorophenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid morpholin-4-ylamide 9 with CB1 receptor in the homology model similar to those of N-piperidino-5-(4- chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-3-pyrazole-carboxamide (rimonabant) 1 and 4S-(-)-3-(4-chlorophenyl)-N-methyl-N′-[(4-chlorophenyl) -sulfonyl]-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamidine (SLV-319) 2.

Skraup-Doebner-Von Miller quinoline synthesis revisited: Reversal of the regiochemistry for γ-aryl-β,γ-unsaturated α-ketoesters

A reversal of the standard regiochemistry of the Skraup-Doebner-Von Miller quinoline synthesis was observed when anilines were condensed with γ-aryl-β,γ-unsaturated α-ketoesters in refluxing TFA. The reaction is proposed to involve 1,2-addition of the ani

Deracemisation of aryl substituted α-hydroxy esters using Candida parapsilosis ATCC 7330: Effect of substrate structure and mechanism

Candida parapsilosis ATCC 7330 was found to be an efficient biocatalyst for the deracemisation of aryl α-hydroxy esters (65-85% yield and 90-99% ee). A variety of aryl and aryl substituted α-hydroxy esters were synthesized to reflect steric and electronic effects on biocatalytic deracemisation. The mechanism of this biocatalytic deracemisation was found to be stereoinversion.

A straighforward route to E-γ-aryl-α-oxobutenoic esters by one-step acid-catalysed crotonisation of pyruvates

A new and highly simple method for the synthesis of E-γ-aryl-α-oxobutenoic esters is described. This unprecedented one-step procedure is based on an unexpected nucleophilic reactivity of alkyl pyruvates towards aromatic aldehydes in refluxing dichloromethane, when using catalytic amounts of Cu(OTf)2 and in the presence of stoichiometric amounts of trimethyl orthoformate in the case of electron-rich aldehydes. Under these conditions, yields obtained are uniformly higher than those obtained by previous multistep procedures.

RING-OPENING OF 4-ISOXAZOLINES: COMPETITIVE FORMATION OF ENAMINO DERIVATIVES AND α,β-ENONES

Ring-opening of 3-substituted 4-isoxazolines, proceeding through the intermediate isoxazolinium salts, follows two competing reaction pathways leading to α,β-enones and enamines respectively.The rearrangement courses can be controlled as a function of substitution pattern and experimental conditions.

A New Synthetic Method for α-Oxo-β,γ-unsaturated Esters

α-Oxo-β,γ-unsaturated esters have been prepared in moderate to good yields via a two-step procedure consisting of the boron trifluoride-promoted reaction of 2-(trimethylsiloxy)acrylic esters with acetals, followed by treatment with silics gel in benzene u