Styryl methyl ketone

The succinct synthesis of warfarin starts with condensation of ort/zo-hydroxy-acetophenone (1-2) with ethyl carbonate to give the (3-ketoester (1-3) as the presumed intermediate shown in the enol form. Attack of the phenoxide on the ester grouping will lead to cyclization and the formation of the coumarin (1-4). Conjugate addition of the anion from that product to methyl styryl ketone (1-5) gives the corresponding Michael adduct and thus warfarin (1-6) [1]. 

The Sn2 mechanism is ruled out for reaction between the tertiary halide, r-BuBr, and radical anions derived from the more easialy reduced compounds cinnamonitrile (9) ethyl cinnamate (12a), methyl styryl ketone (23a), and phenyl styryl ketone (20a). Reduction of the activated alkenes in the presence of an excess of r-BuBr leads to mixtures of products where a r-Bu group has been introduced in a- or j0-position or in the phenyl ring. For 9 and 12a small amounts of butylated hydrodimers were obtained in addition, and for the enone 23a formation of the unsaturated alcohol with introduction of the /-Bu group at C-1 was a major product [192]. In this case the mechanism is unambiguously reduction of the activated alkene followed by electron transfer to r-BuBr concerted with halide cleavage, in... 

Heterocycles containing One Sulphur Atom Thiopyrans. - A convenient synthesis of 2-phenylthiopyran-4-one (217) has been developed from methyl styryl ketone and ethyl formate. The enolate... 

Beilstein Handbook Reference) Aceto-cinnamone AI3-00944 Benzalaceton Benzalacetone Benzilidene acetone Benzilideneacetone Benzylidene-acetone BRN 0742046 3-Buten-2-one, 4-phenyl- CCRIS 5319 EINECS 204-555-1 FEMA No. 2881 Ketone, methyl styryl Methyl 2-phenylvinyl ketone Methyl styryl ketone Methyl (3-styryl ketone NSC 5605 4-Phenylbutenone 4-Phenyl-3-buten-2-one 2-Phenylvinyl methyl ketone Styryl methyl ketone. Used in organic synthesis and perfumery used as a fixative and in flavors. Solid mp = 41.5°. Lancaster Synthesis Co. Penta Mfg. Raschig GmbH. 

Methyl styryl ketone. See Benzylidene acetone Methyl succinate. See Dimethyl succinate Methylsufone. See Dimethyl sulfone 5-Methyl-3-sulfanilamidoisoxazole. See Sulfamethoxazole... 

Qraebe, Jequier, Ann., 1896, 29Q, 204. Benzylideneacetone Benzalaceione, methyl styryl ketone, acetocinnamone)... 

Dypnone n. (phenyl a-methyl styryl ketone, l,3-diphenyl-2-butene-l- one) C6H5COC HC(CH3)C6H5. a plasticizer and ultraviolet absorber. 

Addition of aldehydes to activated carbon-carbon double bonds occurs smoothly in the presence of cyanide ions as catalysts. - E A soln. of methyl styryl ketone in dimethylformamide added dropwise at ca. 35° to a stirred soln. of p-diloro-benzaldehyde and NaCN in the same solvent, and stirring continued 1-4 hrs. 

Methyl styryl ketone and distyryl ketone, typical a,/3-unsaturated ketones, add thiocyanogen in unstated yields. Few other substances of the a,/3-unsaturated carbonyl type have been examined. It is reported, however, that maleic, fumaric, acrylic, crotonic, and cinnamic acids do not react with thiocyanogen. ... 

Takaki reports that ketone enolates add to dimethylstyryl sulfonium perchlorate (155) or methyl styryl sulfone (156) in a Robinson-type annulation sequence to afford the corresponding 3-hydroxythiadecalin (157) or 5-dioxide (158), respectively subsequent reductive desulfonation of (158) affords diene (159).131 However, additions to acceptor (155) suffer from competing cyclopropanation which is dependent on the electrophilicity of the carbonyl group and the ring size of the ketone (Scheme 61). As an aside, DeLucchi reports that l,l-bis(benzenesulfonyl)ethylene (160) adds to ketones at the more substituted a-carbon under neutral conditions in refluxing acetonitrile (equation 18).132... 

Methyl-8-formylBIPS (71, Z = O) was condensed with amines to give in 36-61% yields the 8-anils (Z = N-R) (R = benzyl and 4-X-phenyl, [X = acetyl, nitro, and methyl]), and with aldehydes to give in 62-76% yields the 8-styryl ketones (Z=CH-R ) (R = methyl, phenyl, and 2-hydroxyphenyl). The styryl ketones were shown by their NMR spectra to be the cis isomers. Of the anils, only the 4-nitrophenyl... 

C11H11N02 ethyl 2-cyano-2-phenylacetate 4553-07-5 548.15 48,529 2 21897 C11H1203 methyl-3-methoxy-4-hydroxy styryl ketone 1080-12-2 507.15 44.572 2... 

Polymers containing the methyl methacrylate moiety followed by a spacer and a chalcone moiety are photocrosslinkable [30]. A chalcone contains the phenyl carbonyl ethylene phenyl sequence, or a phenyl styryl ketone. A methacrylate containing example is 4-[4[biphenyl oxy carbonyl phenyl oxy carbonyl] phenyl carbonyl ethylene phenyl] oxy butyl methacrylate. 

C23H16O, 9-Anthryl styryl ketone, 41B, 194 C2 Hi7Br, 10-Bromo-1,8-diphenylanthracene, 46B, 138 C2HH33CIF3NO2, ( + )-cis 9-(3-Dimethylaminopropyl)-lO-methyl-2-(trifluoromethyl)-9,10-dihydroanthracene hydrochloride monohydrate acetone solvate, 42B, 125... 

The 1,4-conjugate addition of ketones to a, 3-unsaturated ketones, under protic conditions, was reported by Stobbe in 1912 "8a further developments afforded protocols for the synthesis of fused cyclo-hexenones, i.e. Robinson annulation.ll8lwl Robinson also reported that aprotic 1,4-conjugate additions of select reagents, e.g. sodiocyclohexanone with styryl methyl ketone,"9 was preferable to the protic addi-... 

F. Dobler, on aromatio aldehydes F. Bidet, on primary amines, etc. G. Baume, and A. M. Wasilieff studied the system with methyl ether and ethyl alcohol with ammonia and C. A. Kraus and E. H. Zeitfuchs, equilibrium in liquid mixtures of ammonia and xylene. H. H. Schlubach and H. Miedel observed that ammonia or ammonium salts may act as a reducing agent on some organic compounds—phenyl-butylene, styryl methyl ketone, pyridine, and nitrobenzene, but not acetophenone, benzil, benzoin, and deoxybenzoin. A soln. of sodium in liquid ammonia is added gradually to a soln. of ammonium chloride in the same solvent in which the substance to be reduced is at least partly dissolved at —80° to —50°. If the compound under investigation is not sufficiently soluble in liquid ammonia, benzene or ether... 

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