1-Acetyl-l-cyclohexene

Acetyl-l-cyclohexene 1-Norephedrine Palladium on carbon Aluminum chloride... 

Isomerization of ethynylcarbinols. Rupe12 first observed that ethynylcarbinols when refluxed in formic acid (90%) are isomerized to unsaturated carbonyl compounds, which he considered to be aldehydes. Chanley13 later investigated the reaction in detail and found that the predominant product is an a,/ -unsaturated ketone. Thus 1-ethynyl-l-cyclohexanol (1) is converted mainly into 1-acetyl-l-cyclohexene (2), with onLy traces of (3) being formed. 

An 0X0 or alkoxy group is introduced at the allylic position of 2-cyclopentenones depending on their substitution pattern, as shown in Scheme 2.46 [107]. Similarly, 1-acetyl-l-cyclohexene undergoes allylic oxidation to give l-acetyl-3-ethoxy-l-... 

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... 

Treatment of 1-morpholino-l-cyclohexene with ketene gives l-morpholino-2-acetyl-l-cyclohexene251 as the main product, whereas enamines prepared from aliphatic aldehydes yield cyclo-butanones.252,253 Ketene may be generated directly in the reaction medium from acid chlorides and triethylamine. 

Alkoxybicyclo[2.2.2]octan-2-ones. A soln. of 4-acetyl-1-methoxy-l-cyclohexene and p-toluenesulfonic acid in isobutanol refluxed 3 hrs., then slowly distilled to remove the solvent during 3-4 hrs. 4-isobutoxybicydo [2.2.2] octan-2-one. Y 76%. Also without transetherification and in other alcohols s. K. Morita and T. Kobayashi, J. Org. Chem. 31, 229 (1966) 4-aminobicydo[2.2.2]octan-2-ones s. J. Org. Chem. 31, 3106 cycloisomerization in benzene s. Y. Gaoni and R, Mechoulam, Am. Soc. 88, 5673 (1966). 

The preparation of 4-alkoxybicyclo [2.2.2] octan-2-ones from 4-acetyl-1-methoxy-l-cyclohexene by a novel cycloisomerization of 1,3-disubst. adamantanes by an exceptionally easy ring closure from suitable unsatd. cycloketones , and of cubane derivatives by an elegant three-step procedure have been reported. 

The purity of the product was determined by the checkers by GLC analysis using the following column and conditions 3-nm by 1.8-m column, 5% free fatty acid phase (FFAP) on acid-washed chromosorb W (60-80 mesh) treated with dimethyldichlorosilane, 90 C (1 min) then 90 to 200 C (15°C per rain). The chromatogram showed a major peak for methyl 2-methyl-l-cyclohexene-l-carboxylate preceded by two minor peaks for methyl 1-cyclohexene-l-carboxylate and l-acetyl-2-methylcyclohexene. The areas of the two impurity peaks were 5-6% and 0.5-2% that of the major peak. The purity of the product seems to depend upon careful temperature control during the reaction. The total amount of the two impurities was 14-21% in runs conducted at about -15 to -20°C or at temperatures below -23°C. 

The mild character of the reaction conditions is exemplified effectively here by the preparation of 2-acetyl-2-cyclohexen-l-one from 2-acetyIcyclohexanone. The crude product is initially isolated entirely in the less stable enedione form which is partially converted to the more stable enol form, 2-ace tyl-1,3-cyclohexadien-l-ol, during distillation at 45-55°. A series of a,(3-unsaturated j3-keto esters, -diketones, and a p-keto sulfoxide have also been prepared in the unenolized form by this... 

Acetylacetonylbenzoic acid, 58, 55, 56 2-Acetyl-l,3-cyclohexadien-l-ol, 59, 62 Acetylcyclohexane, 55, 25 2-Acetylcyclohexanone, 59, 59 2-ACETYL-2-CYCLOHEXEN-1-ONE, 59,... 

Acetyl-l-methyl-l-cyclohexene [6090-09-1] M 138.2, 73-75 /7.5mm, 85-86 /13mm, 94-94.7 /20mm, 204.5-206 /747mm, d 1.0238, n p 1.469. Purified by fractionation under reduced pressure in vacuo, and when almost pure it can be fractionated at atmospheric pressure, preferably in an inert atm. Forms two semicarbazones one of which is more soluble in C H, and both can be recryst from EtOH, more soluble has m 149 (151 ), and the less soluble has m 172-175°(191°). 4-Nitrophenylhydrazone has m 166-167° and the 2,4-dinitrophenylhydrazone has m 114-115 . [/7CA 17 129, 140 1934 A 564 109 7949]. 7V-Acetyl-67V -methylglycinamide [7606-79-3] M 130.2. Recrystd from EtOH/Et2O mixture. 7V-Acetyl-67V -methyl-L-leucine amide [32483-15-1 ] M 186.3. Recrystd from EtOH/hexane mixture. 

The aldehyde (163), which was prepared from 160 by periodic acid oxidation, was further converted into pseudo-a-D-mannopyranose as follows. Dehydration of 163 with mesyl chloride and pyridine, and subsequent reduction with lithium aluminium hydride gave (3S, 4R, 5S)-3,4,5-tris(benzyloxy)-l-cyclohexene-1-methanol (164). Hydroxyla-tion of 164 with diborane and hydrogen peroxide yielded 4,6-di-0-acetyl-l,2,3-tri-0-... 

Certain A-acetyl-a-amino acids may also be prepared from diolefins, including dicyclopentadiene, 4-vinyl-l-cyclohexene, 1,3-butadiene and 1,7-octadiene (Table 1). Monoamido acids are the predominant products obtained from unsym-metrical dienes, such as dicylopentadiene and 4-vinyl-l-cyclohexene diamido acids are formed from symmetrical dienes. A number of these polyamido acids have potential as chelating agents. 

Acetyl-1-cyclohexene Ethanone, l-(l-cyclohexen-l-yl)- (932-66-1), 76, 203 Acetylenes, terminal, cyanation of, 75, 148... 

Acetyl-aromaten lassen sich durch Natrium/Alkohol zu den entsprechenden Alkoholen reduzieren (s. ds. Handb. VII/2b, S. 1993), wahrend Diarylketone unter diesen Bedingun-gen zu Diarylmethanen reduziert werden. Natrium/Ammoniak ist fiir die Reduktion von Acetyl-aromaten zur Alkohol-Stufe ungeeignet. Dagegen labt sich 3-Acetyl-phenol durch Natrium/Ammoniak/Athanol zu 1 -(3-Hydroxy-phenyl) -dthanol (F 116°) reduzieren1. Bei der Reduktion von Acetophenon mit Lithium/Athylamin wird zwar die Alkohol-Stufe, jedoch unter teilweiser Reduktion des Aromaten erhalten. In 65%-iger Ausbeute ent-steht l-[Cyclohexen-(l)-yl]-athanol2 (Kpls 86-87°). 

Cyclohexanon Mesityloxid I - Acetyl-cyclohexen 3-Oxo- l-phenyl-buten-( 1)... 

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