2-Methyl-l ,2-epoxypropane

We also note that some 2,2-disubstituted oxiranes have toxicological significance, as exemplified by 2,2-dimethyloxirane (2-methyl-l, 2-epoxypropane, 10.43, R = Me). This compound is the toxic metabolite of 2-methyl-prop-1-ene (isobutene), a gaseous alkene widely used as a monomer in the industrial production of adhesives, plastics, and other polymers. Interestingly, detoxification of this epoxide catalyzed by liver epoxide hydrolase was high in the human, intermediate in the rat, and low in the mouse [125], These activities were inversely correlated with the epoxide levels measured in vitro in liver tissue of these species. 

The regiochemistry of acid-catalyzed ring-opening depends on the epoxide s structu re, and a mixture of products is often formed. When both epoxide carbon atoms are either primary or secondary, attack of the nucleophile occurs primarily at the less highly substituted site—an S]s 2-like result. When one of the epoxide carbon atoms is tertiary, however, nucleophilic attack occurs primarily at the more highly substituted site—an S l-like result. Thus, 1,2-epoxypropane reacts with HCl to give primarily l-chloro-2-propanol, but 2-methyl-l,2-epoxypropane gives 2-chloro-2-methyl-l-propanol as the major product. 

The utility of the creation of a y-lactone enolate through 1,4-addition of a carbanion and its interception by an electrophile has also been demonstrated in other classes of natural products, e.g., in the enantioselective synthesis of 10-oxa-l 1-methyl PGE2 analogues22. This synthesis starts with 1,4-addition of the sulfone-stabilized anion from 27 to ( + )-(S )-4-methyl-2-buteno-lide which has been prepared in three steps from (—)-(S)-l,2-epoxypropane. The intermediate enolate 28 is reacted with the acetylenic iodide to give the trisubstituted diastereomeric mixture of lactones 29, which is eventually converted into the pure compound 30, both reactions occurring with high diastereoselectivity. 

Synonyms AGE AI3-37791 AllyE2,3-epoxypropyl ether l-Allyloxy-2,3-epoxypropane BRN 0105871 CCRIS 2375 EINECS 203-442-4 l,2-Epoxy-3-allyloxypropane Glycidyl allyl ether M 560 NC1-C56666 NSC 18596 [(2-Propenyloxy)methyl]oxirane UN 2219. 

The epoxide ring of methyl crotonate has been reposted to undergo addition of methanol on the carbon atom furthest from the u l<-r function (Eq. 574), giving methyl 2-hydroxy-3-methoxybutyrato.4"5 Alcoholysis of 1,1 -dioarbethoxy-1.2-epoxypropane in the presence of acid has also been carriod cut.1310 Although not definitely established, it is nevertheless probable that addition likewise takes plaoe at thr epoxide carbon atom farthest removed from the ester substituents. 

To an ice-cooled solution of N-methyl-l-naphthalenemethylamine hydrochloride (2.1 g) in methanol (40 ml) and water (10 ml) was added sodium hydroxide powder (2 g) followed by dropwise addition of epichlorohydrin (8 ml). The mixture was heated at 60°C for 3 h, then cooled to room temperature. Volatile materials were removed in vacuo and the residue was taken up in ethyl acetate and washed with water. The organic phase was collected, dried over sodium sulfate, filtered and evaporated to dryness. The crude mixture was purified by flash chromatrography on silica gel (grade 9385, Merck, 230-400 mesh, 60 A) using a solvent gradient of a mixture of hexane and ethyl acetate (95 5, 90 10 and 85 15) as eluent, affording the N-methyl-N-naphthylmethyl-2,3-epoxypropane (1.85 g, 81.5%) as an oil. 

Acetone, bromoethane, butane, chloroethane, 2-chloropropane, 1,3-cyclopenta-diene, dibromodifluoromethane, 1,1-dichloroethane, 1,1-dichloroethene, 1,2-di-chloro-l,l,2,2-tetra luoroethane, diethylether, dimethoxymethane, dimethylpro-pane, 1,3-epoxypropane, ethyl formate, glyoxal, methyl acetate, methylbutane, methyl formate, methylpropane, -pentane, propanal. 

See Poly [oxy (methyl)sily lene] l-Allyloxy-2,3-epoxypropane See Other ALLYL COMPOUNDS, 1,2-EPOXIDES... 

SYNONYMS AGE, l-allyloxy-2,3-epoxypropane, [(2-propenyloxy)methyl]oxirane... 

El-Amamy and Mill (1984) measured the effect of the surface acidity of mont-morillonite and kaolinite on the hydrolysis rate constants for a number of chemicals containing hydrolyzable functional groups that exhibit acid-catalyzed, base-catalyzed, and neutral hydrolysis. The chemicals that were studied included ethyl acetate, cyclohexene oxide, isopropyl bromide, l-(4-methoxyphenyl)-2,3-epoxypropane, and N-methyl-p-tolyl carbamate (MTC). Aqueous suspensions of... 

Recently, in our laboratory, polypropylene sulfides with an asymmetric lateral aminated chain have been prepared and described by Huguet et al [110—112]. OA oxiranylalkyl-amines have been synthesized by reaction of l-chloro-2,3-epoxypropane on iS-methyl-1-propylamine (XLVa) or S -phenyl-l-ethylamine (XLVh) and the reaction of potassium thiocyanate with the amino-oxiranes gave the thiiranyl derivatives without any perceptible racemization. 

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