4-acetyl-5-methyl-2-phenyl

Imidazole, 4-acetyl-5-methyl-2-phenyl-synthesis, 5, 475 Imidazole, 1-acyl-reactions, 5, 452 rearrangement, 5, 379 Imidazole, 2-acyl-synthesis, 5, 392, 402, 408 Imidazole, 4-acyl-synthesis, 5, 468 Imidazole, C-acyl-UV spectra, 5, 356 Imidazole, N-acyl-hydrolysis rate constant, 5, 350 reactions, 5, 451-453 synthesis, 5, 54, 390-393 Imidazole, alkenyl-oxidation, 5, 437 polymerization, 5, 437 Imidazole, 1-alkoxycarbonyl-decarboxylation, 5, 453 Imidazole, 2-alkoxy-l-methyl-reactions, 5, 102 thermal rearrangement, 5, 443 Imidazole, 4-alkoxymethyl-synthesis, 5, 480 Imidazole, alkyl-oxidation, 5, 430 synthesis, 5, 484 UV spectra, 5, 355 Imidazole, 1-alkyl-alkylation, 5, 73 bromination, 5, 398, 399 HNMR, 5, 353 synthesis, 5, 383 thermal rearrangement, 5, 363 Imidazole, 2-alkyl-reactions, 5, 88 synthesis, 5, 469... 

TTie true ketones, in which the >CO group is in the side chain, the most common examples being acetophenone or methyl phenyl ketone, C HjCOCH, and benzophenone or diphenyl ketone, C HjCOC(Hj. These ketones are usually prepared by a modification of the Friedel-Crafts reaction, an aromatic hydrocarbon being treated with an acyl chloride (either aliphatic or aromatic) in the presence of aluminium chloride. Thus benzene reacts with acetyl chloride... 

Acetophenone. Acetophenone [98-86-2] (methyl phenyl ketone) is a colorless Hquid that forms laminar crystals at low temperature (mp 20°C). It has a characteristic sweet orange blossom odor, and is soluble in alcohols and ethers. It is found in nature in oil of casatoreum, obtained from beavers oil of labdanum, recovered from plants and in buds of balsam poplar. It can be prepared by the Friedel-Crafts reaction (qv) of acetyl chloride with benzene in the presence of aluminum chloride however, this route is of Htde commercial significance. 

Cyclopentane, 1-cyano-l-phenyl-, 55, 94 Cyclopentane, methyl-, 55, 62, 112 Cyclopropane, 1-acetyl-1-phenyl-, 55, 94... 

Cyclohexene-l,4-dione, 2,3,5-tiichloro-3, 6-bis(l,l-dimethylethyl)- [5-Cyclo-hexcne-1,4-dione, 2,3,5-tnchloio-3,6-dwert-butyl-], 55, 33 Cyclopentadiene, 55, 15,16 Cyclopentane acetyl-,55,25 Cyclopentane 1-cyano-l-phenyl-, 55,94 Cyclopentane methyl-, 55, 62 Cyclopropane, 1-acetyl-l-phenyl-, 55 94... 

N-Diphenylmethylen- 374 N-Diphenylmethylen-O-aminocarbonyl- 612 N-[l,3-Diphenyl-propyl-(2) - 374 N-[l,3-Diphenyl-propyliden-(2)]- 374, 377, 380 N-(4-Halogen-phenyI)- 683 N-Heptyl- 375 N-Heptyl-N-acetyl- 376 N-Heptyliden- 375 N-Hcptyliden-O-acetyl- 376 0-(2-Hydroxy-athyl)-N-athoxycarbonyl- 133 N-(4-Hydroxy-phenyl)- 683 0-(2-Hydroxy-l-phenyl-athyI)-N-athoxycarbonyI-aus 0-(ci-AthoxycarbonyI-benzyl)-N-athoxycar-bonyl-hydroxylamin und Lithiumalanat 133 N-Isopropyl- 682 N-Isopropylidcn- 613 N-Methyl- 133, 682 O-Methyl-N-bcnzyliden- 377 O-Methyl-N-benzyliden- 375 0-Methyl-N-(4-chlor-benzyl)- 375 0-Methyl-N-(4-chlor-benzyliden)- 375 N-Methy -N,0-diacetyI- 682 N-(4-Methyl-phenyl)- 683 0-McthyI-N-( 1 -phenyl-athyliden)- 375 N-(4-Methylthio-phenyl)- 684 N-(4-Nitro-benzyl)- 374 N-[4-Nitro-benzyliden - 374, 377 N-(2-Nitro-phenyl)- 562 N-(4-Nitro-phenyl)- 682 N-Nitroso-N-cyclohexyl- 697 N-Octyl- 374 N-Octyl-(2)-N-acetyl- 376 N-Octyliden- 374 N-0ctyliden-(2)-0-acctyl- 376 N-(Pentafluor-phenyl)-0,N-diacetyl- 697 N-Phenyl- 474, 481, 682, 783 N-Phenylacetyl-O-benzoyl- 265 N-(l-Phenyl-athyl)- 374 N-(l-Phenyl-athyl)-N-acetyl- 376 N-(l-Phenyl-athyliden)-374, 613 N-( l-Phenyl-athyliden)-0-acetyl- 376 N-[ 1 -Phenyl-buten-( 1 )-yl-(3)-iden]- 582 N-f4-Phenyl-butyl-(2)-iden]- 581 N-Phcnyl-N,0-diacetyl- 682 N-(4-Phenylthio-phenyl)- 684 N-Propyl-N-cyclohexyl- 376 N-Propyl-N-isopropyl- 376 O-Sulfonyl- 481 N-(4-Sulfonyl-phenyI)- 683 N-(2-Vinyl-phenyl)- 698... 

The structures of several compounds containing the pyrrolo[l,2,4]triazine moiety have been established by X-ray crystallography, as for example pyrrolo[l,2- ][l,2,4]triazine 13 <1997J(P1)1829>, 4-acetyl-l-phenyl-2a,3,5-triaza-benz[r-,<7]azulene 14 <2000H(53)323>, heterodiquinane 15 <1998CL1135>, cation 16 derived from methylation of 3-phenylcyclohepta[4,5]pyrrolo[l,2- ][l,3,5]triazine-2,4(377)-dione <2005H(65)1629>, 2-phenyl-3-phenyl-... 

Simple empirical rules for assigning diastereomeric compounds can be found frequently in literature on stereoselective reactions. In a typical example, the vinyl methyl protons of 13a have a smaller chemical shift (3 = 1.68) than those of isomer 13b (3 = 1.74), apparently due to the proximity of the phenyl group. Accordingly, the sequence of the acetyl methyl protons is reversed394. 

Bei den folgenden zwei Typen von Cyclokondensationen, die z. B. zu 4-Acetyl-2-phenyl-1-propyl-pyrrolidin3 bzw. 2-Benzyl-5-methyl-6-oxo-cis-2-aza-bicyclo[3.3]octan fiihren, er-folgt intermediar eine [3.3]-sigmatrope Umlagerung eines N-(3-Alkenyl)-iminium-Ions ... 

PENTAMETHYL-, 56, 1 Cyctopentane, acetyl-, 55, 25 Cyclopentane, 1-cyano-l-phenyl-, 55, 94 Cyclopentane, methyl, 55, 62 Cyclopentanol p-toluenesulfonate, 55, 112 Cyclopentene, 56, 34, 58, 73 2-Cyclopenten-l-one, 2,5-dialkyl- 58, 62 CYCLOPENTENONES, 58, 56 Cyclopropane, 1 -acetyl-1 -phenyl-, 55, 94 Cyclopropane, 1, l-dibromo-2,2-diphenyl-, 56, 32... 

N-Methyl-N-phenyl acetamide, 114 N-Methyl-N-phenylformamide, 113 Methyl phenyl glyoxalate, 327 N-Methyl-N-phenyl propionamide, 114 N-Methylpiperidone, 117 Methyl 2,3,4,6-tetra-0-acetyl-6-D-glucopyranoside, 85... 

Diketones are synthesized by Claisen condensation of appropriate acetyl methyl ketone and ethyl perfluoroalkyl carboxylate. For example, 4,4/-bis(l",l,/,l//,2//,2",3//,3//-heptafluoro-4//,6//-hexanedion-6"-yl)-chlorosulfo-o-terphenyl (BHHCT) was synthesized from o-terphenyl by three step reactions (scheme 3 (Yuan et al., 1998a, 1998b)). The o-ter-phenyl are acetylated by acetyl chloride with anhydrous aluminum chloride as a Lewis acid and 4,4 -diacetyl-e>-terphcnyl is obtained. Then, the 4,4/-diacetyl-o-terphenyl is reacted with perfluoropropionic acid ethyl ester with sodium methoxide as a base. Finally, 4,4,-bis(l", 1",l//,2,2,3,/,3"-heptafluoro-4//,6"-hexanedion-6//-yl)-o-terphenyl is chloro-sulfonylatcd by chlorosulfonic acid to form BHHCT. 

The acetyl-methyl group in 2-acctylphenyl methyl tellurium condenses with benzaldehyde to give methyl 2-(3 -phenyl-2 -propen-l -oyl)phenyl tellurium3. 

Acetylphenyl butyl tellurium is formylated at the acetyl-methyl group by methyl formate and sodium in diethyl ether. The formyl compound is converted to butyl 2-(diazoacetyl)-phenyl tellurium upon treatment with 4-methylbenzenesulfonyl azide1. The diazoacetyl group is converted to the dibromoacetyl group by bromine in diethyl ether1. 

Methyl phenyl acetyl acetate Benzenebutanoic acid, -oxo-methyl ester (9) (37779-49-0)... 

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... 

In the 1980 s, we showed that THC-type compounds exhibit very high stereospecificity of cannabinoid action [20-24], Some of the previous observations regarding lack of stereospecificity were apparently due to separation problems. The (-)-enantiomer of d8-l 1-hydroxy-THC-DMH (3) (HU-210) (DMH=l,l-dimethylheptyl) was shown to be several thousand times more potent than the (-i-)-enantiomer (HU-211) (4) in a series of animal tests. The synthesis of HU-211 is presented in Figure 5.2 [25]. The intermediate (+)-4-oxo-myrtenyl pivalate (5), and its (-)-enantiomer are highly crystalline and can be obtained essentially stereochemically pure by recrystallization. This lucky observation made possible the ultimate synthesis of both enantiomers, HU-211 and HU-210, ine.e. higher than 99.8%, as determined by HPLC analysis of the respective diastereoisomeric bis-(S) (+)-a-methoxy-a-(trifluoro-methyl)phenyl-acetyl (MTPA) esters [25], Nonclassical cannabinoids were also shown to exhibit high stereospecificity of cannabinoid activity [21, 26]. 

Among other electrophilic reagents ctq>able of twinging about the Pummerer rearrangement are halides of organic and inorganic acids. As these halides transform sulfoxides into a-chlorosulfides they complement the sulfide chlorination route to these compounds. Thionyl chloride reacts readily with sulfoxides and 3-keto sulfoxides methyl phenyl sulfoxide furnishes chloromethyl phenyl sulfide (equation 37). Benzoyl chloride and acetyl chloride behave similarly. d yanuric chloii is transformed into cyanuric acid by dimethyl sulfoxide, which in turn is transformed into methyl chloromethyl sulfide (equation 3g).54,S5... 

Acetyl-l-nitroso-l-phenyl- X/2, 393 2-Formyl-l-(4-methyl-phenyl)-l-... 

Oxiran trcms-3-( Diazo-acetyl)-2-phenyl- E14b, 1194 (Oxiran-Bild.) Propansaure 2-Hydroximino-3-(4-methyl-phenyl)-3-oxo- -nitril X/4, 159... 

Amino-3-benzylthio- XV/I, 736 2-Amino-3-mercapto- -benzylester (Hydrochlorid) XI/2, 357 Sulfoximid S-(2-Acetyl-4-methyl-phenyl)-S-methyl- Ell, 1303 (RjSO + HN3)... 

Thiadiazol 5-(2-Acetyl-hydrazino)-2-(2-methyl-phenyl)-E16a, 798 (N-Acylier.)... 

Propandiol threo-2-Acetyl-amino- 1 -(2-methyl-phenyl)-IV/Id, 213... 

Peroxid tert.-Butyl-[(2-methyl-phenyl)-acetyl]- E13/1, 807/814 (Cl - O-OR)... 

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