70453-19-9

Upstream product

• 704-80-3 (E)-3-phenyl-2-butenoic acid 
• 1895-97-2 2-methyl-3-phenylacrylic acid 
• 98-86-2 acetophenone 
• 704-79-0 (Z)-3-phenylbut-2-enoic acid 
• 1504-72-9 ethyl 3-phenylbut-2-enoate 
• 704-79-0 3-phenylbut-2-enoic acid 
• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 

Downstream Products

• 147729-73-5 3-phenyl-1-(2,4,6-trimethoxy-phenyl)-but-2c-en-1-one 
• 1628-63-3 2-((E)-2-phenyl-propenyl)-benzothiazole 
• 93011-83-7 7-hydroxy-2-methyl-2-phenyl-chroman-4-one 
• 30154-67-7 (E)-3-Phenyl-but-2-enoic acid 5-((E)-3-phenyl-but-2-enoyloxy)-4-(1-phenyl-vinyl)-biphenyl-3-yl ester 
• 84053-73-6 N-Allyl-N-tert.-butyl-β-methyl-zimtsaeureamid 
• 872509-51-8 (E)-3-Phenyl-but-2-enoyl azide 
• 77302-26-2 (E)-3-Phenyl-but-2-enoic acid allylamide 
• 69910-22-1 3-phenyl-cis-crotonic acid-((S)-1-phenyl-ethyl ester) 
• 69940-86-9 (E)-3-Phenyl-but-2-enoic acid (S)-1-phenyl-propyl ester 
• 750647-29-1 (S)-N-[3-phenyl-2-(E)-butenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 
• 7386-65-4 (2E)-3-phenylbut-2-enamide 
• 1309583-71-8 (E)-1-(4-methoxyphenyl)-3-phenylbut-2-en-1-one 

Relevant academic research and scientific papers

Contra-thermodynamic E → Z isomerization of cinnamamides via selective energy transfer catalysis

A bio-inspired, photocatalytic E → Z isomerization of cinnamides is reported using inexpensive (?)-riboflavin (vitamin B2) under irradiation at λ = 402 nm. This operationally simple transformation is compatible with a range of amide derivatives including –NR2, –NHSO2R and N(Boc)2 (up to 99:1 Z:E). Selective energy transfer from the excited state photocatalyst to the starting E-isomer ensures that directionality is achieved: The analogous process with the Z-isomer is inefficient due to developing allylic strain causing chromophore deconjugation. This is supported by X-ray analysis and Stern-Volmer photo-quenching studies. Preliminary validation of the method in manipulating the conformation of a simple model Leu-enkephalin penta-peptide is disclosed via the incorporation of a cinnamamide-based amino acid.

Design, synthesis and SARs of novel telomerase inhibitors based on BIBR1532

Telomerase has become one of the new popular targets for the development of anti-tumor drugs. Based on the structural characteristics of the BIBR1532 which has entered the stage of clinical research, six series total of 64 new compounds with diverse struc

Synthesis and characterization of unsaturated diacyl and alkyl-acyl piperazine derivatives

The aim of this study is to obtain new unsaturated piperazine compounds by the reactions of piperazine (1a) and piperazine derivatives (1b–1d) with acylation reactive groups (2a–2j). Methacryloyl piperazine (1b) was synthesized from the reaction of methacrylic anhydride with piperazine (1a). Acyl chlorides (2b–2d) were prepared from the reaction of thionyl chloride with carboxylic acids (3a–3c) obtained as a result of the reaction with malonic acid and suitable aldehyde (5-methylfuran-2-carbaldehyde for 3a, cinnamaldehyde for 3b, and thiophene-2-carbaldehyde for 3c), respectively, by literature methods. Acyl chlorides 2e and 2f were obtained from the reaction of commercially purchased carboxylic acids 3d and 3e with thionyl chloride. Acyl chlorides (2g–2j) were synthesized from the reaction of thionyl chloride with carboxylic acids (3d–3g) transformed from hydrolyzation of esters (4a–4d) obtained as a result of the reaction of triethyl phosphonoacetate with a suitable ketone (acetophenone for 4a, benzophenone for 4b, 1-(5-methylfuran-2-yl)ethan-1-one for 4c, and 1-(thiophen-2-yl)ethan-1-one for 4d), respectively, by literature methods. Unsaturated piperazine derivatives 5a and 5b were obtained from the reaction of 1b with 2b and 2e, respectively. In addition, from the reaction of 1b and acyl chlorides (2b–2j), unsaturated piperazines (5c–5k) were synthesized in medium to good yields (63%–84%). Also, 5l–5g and 5r–5w were obtained from the reaction of allyl piperazine (2c) and cinnamyl piperazine (2d) with acyl chlorides (2a–2f).

Intramolecular Nitrofuran Diels-Alder Reactions: Extremely Substituent-Tolerant Cycloadditions via Asynchronous Transition States

Nitrofurans undergo intramolecular Diels-Alder reactions with tethered electron-poor dienophiles more rapidly and in higher yield than non-nitrated furans. Computational studies indicate that increased stabilization of a partial positive charge on the nitro-substituted carbon in both transition state and product is the driving force for these reactions. Frontier molecular orbital energy differences indicate a switch from normal to inverse electron demand upon nitration. There does not appear to be a contribution from any differences in aromatic stabilization energy between furans and nitrofurans. Calculations show that the nitrofuran reactions proceed via a highly asynchronous transition state allowing easier bond formation between two sterically hindered carbons.

Rhodium/bisphosphine-thiourea-catalyzed enantioselective hydrogenation of α,β-unsaturated: N -acylpyrazoles

We successfully extended our Rh/bisphosphine-thiourea (ZhaoPhos) catalytic system to asymmetric hydrogenation of α,β-unsaturated N-acylpyrazoles affording products with high yields and excellent enantioselectivities (up to 97% yield, 99% ee). The pyrazole

Hydroxamic acids block replication of hepatitis c virus

Intrigued by the role of protein acetylation in hepatitis C virus (HCV) replication, we tested known histone deacetylase (HDAC) inhibitors and a focused library of structurally simple hydroxamic acids for inhibition of a HCV subgenomic replicon. While known HDAC inhibitors with varied inhibitory profiles proved to be either relatively toxic or ineffective, structure-activity relationship (SAR) studies on cinnamic hydroxamic acid and benzo[b]thiophen-2-hydroxamic acid gave rise to compounds 22 and 53, which showed potent and selective anti-HCV activity and therefore are promising starting points for further structural optimization and mechanistic studies.

Synthesis of bicyclic guanidines via cascade hydroamination/michael additions of mono- n -acryloylpropargylguanidines

A cascade silver(I)-catalyzed hydroamination/Michael addition sequence has been developed to deliver highly substituted bicyclic guanidines. This transformation gives rise to geometrically and constitutionally stable ene-guanidines and generates a remote stereocenter with moderate to high diastereoselectivity.

N-heterocyclic carbene-catalyzed cyclization of unsaturated acyl chlorides and ketones

A straightforward synthesis of optically active trifluoromethyl dihydropyranones and spirocyclic oxindole-dihydropyranones has been realized by the chiral N-heterocyclic carbenes-catalyzed cyclization of α,β- unsaturated β-methylacyl chlorides with activated trifluoromethyl ketones or isatin derivatives. Copyright

Radical cyclizations of conjugated esters and amides with 3-oxopropanenitriles mediated by manganese(III) acetate

Radical cyclizations of conjugated esters and amides with 3-oxopropanenitriles in presence of manganese(III) acetate produced ethyl 4-cyano-2,3-dihydrofuran-3-carboxylates and 4-cyano-2,3-dihydrofuran-3- carboxamides in good yields. The radical cyclizations of conjugated amides gave 2,3-dihydrofurans in better yields than that of conjugated esters. Moreover, the reactions of thienyl substituted amides and esters with 3-oxopropanenitriles afforded 2,3-dihydrofurans more efficiently than phenyl substituted ones. ARKAT-USA, Inc.

Catalytic asymmetric formation of δ-Lactones from Unsaturated acyl halides

Previously unexplored enantiopure zwitterionic ammonium dienolates have been utilized in this work as reactive intermediates that act as diene components in hetero-Diels-Alder reactions (HDAs) with aldehydes to produce optically active δ-lactones, subunits of numerous bioactive products. The dienolates were generated in situ from E/Z mixtures of a,b- unsaturated acid chlorides by use of a nucleophilic quinidine derivative and Sn (OTf)2 as co-catalyst. The latter component was not directly involved in the cycloaddition step with aldehydes and simply facilitated the formation of the reactive dienolate species. The scope of the cycloaddition was considerably improved by use of a complex formed from Er- (OTf)3 and a simple commercially available norephedrine-derived ligand that tolerated a broad range of aromatic and heteroaromatic aldehydes for a cooperative bifunctional Lewis-acid-/ Lewis-base-catalyzed reaction, providing a,b-unsaturated d-lactones with excellent enantioselectivities. Mechanistic studies confirmed the formation of the dienolate intermediates for both catalytic systems. The active ErIII complex is most likely a monomeric species. Interestingly, all lanthanides can catalyze the title reaction, but the efficiency in terms of yield and enantioselectivity depends directly on the radius of the Ln III ion. Similarly, use of the pseudolanthanides ScIII and YIII also resulted in product formation, whereas the larger La III and other transition metal salts, as well as main group metal salts, proved to be inefficient. In addition, various synthetic transformations of 6- CCl3- or 4-silyl-substituted α,β-unsaturated d-lactones, giving access to a number of valuable δ-lactone building blocks, were investigated.