PULEGONE, - CYCLOHEXANONE

CAS 89-82-7 EINECS/ELINCS 201-943-2 Synonyms Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (R)- (R)-2-lsopropylidene-5-methylcyclohexanone (R)-(+)-p-Menth-4(8)-en-3-one (R)-p-Menth-4(8)-en-3-one (R)-5-Methyl-2-(1-methylethylidene) cyclohexanone Pulegon Pulegone (+)-Pulegone (+)-(R)-Pulegone (R)-(+)-Pulegone Classification Nonaromatic ketone Definition Ketone found in pennyroyal and dedeoma oil Empirical CioHieO Properties Oily liq. pleasant odor of peppermint/camphor misc. with alcohol, ether, chloroform pract. insol. in water m.w. 152.26 dens. 0.936 b.p. 224 C flash pt. 185 F ref. index 1.4870... 

MANGANESE-COPPER-CATALYZED CONJUGATE ADDITION OF ORGANOMAGNESIUM REAGENTS TO a,p-ETHYLENIC KETONES PREPARATION OF 2-(1,1-DIMETHYLPENTYL)-5-METHYL-CYCLOHEXANONE FROM PULEGONE (Cyclohexanone, 2-(1,1-dimethylpentyl)-5-methyl-)... 

Two new types of optically active 1,3-oxazines (41) were synthesized by Rassat and Rey (74T265, 74T3315). The epimeric 1,3-amino alcohols 40, prepared from (-l-)-pulegone 39 by Michael addition of ammonia and subsequent reduction, were cyclized with acetone, cyclohexanone, and 4-tert-... 

Cyclohexanone and pulegone provide useful examples to illustrate ring expansion and ring contraction procedures. 

Pulegone (= 1-Methyl-4-isopropylidene-3-cyclohexanone) Hedeoma pulegundes (American pennyroyal oil), Menthapulegium (European pennyroyal oil) (Lamiaceae) OD-R... 

Recently Avery et al [94] have developed a stereoselective total synthesis of (+)-artemisinine starting from (R)-(+)-pulegone (92). Elaboration of 92 gives the known sulphoxide 93, which was allowed to undergo dianion alkylation and desul-phurisation to yield disubstituted-cyclohexanone (95). Homologation of the latter afforded the aldehyde % in two steps. This product was then converted into the silyl acetate (97), which underwent Tandem Claisen ester-enolate rearrangement to give the vinylsilane 98. Ozonolysis and cyclisation of 98 provided 7 (Scheme 10). 

Since 0 or 1 and perhaps 2 double bonds anywhere in the lefthand ring above, as well as changes in the size and position of the alkyl groups will probably all produce compounds with THC activity, many compounds similar to menthadieneol, men-thatriene, verbenol, epoxycarene, pulegone and 4-carbethoxy-l-Me-3-cyclohexanone can be used in the methods below to get active THC analogs (e.g., isopiperitinol will work [TL 945... 

Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2S-trans)-. See l-Menthone Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (R)-. See d-Pulegone... 

Methyl-2-(1-methylethyl) cyclohexyl] oxy]-1,2-propanediol. See Menthoxypropanediol (R)-5-Methyl-2-(1-methylethylidene) cyclohexanone. See d-Pulegone 1-Methyl-4-(1-methylethylidene) cyclohexene. See Terpinolene... 

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