Methyl 3-methylcrotonate

V,7V-dimethylaminopyridme provides l-(2-methoxycarbonyl)ethoxy- (40,69%) and l-(2-methoxycarbonyl-l-methyl)ethoxytryptamine (41, 72%), respectively (Scheme 4). The conjugate addition to mesityl oxide proceeds successfully as well, giving iVb-acetyl-1-(1, l-dimethyl-3-oxo)butoxytryptamine (42,49%), while the reaction with methyl 3-methylcrotonate affords 43 in a miserable yield (1.6%). Addition to acrolein results in failure, and 44 is not yet obtained. 

When the cyclopropanone ring is unsymmetrically substituted, two radicals are produced if C1—C2 and Ci—C3 cleavages are competitive. In the reaction of l-methoxy-2,2-dimethylcyclopropanol with cupric ion, product studies indicate that approximately twice as much primary radical (143) is produced as tertiary (144) (Table 19). Although these two radicals would be expected to condense with methyl (3-methylcrotonate (145), addition of 145 to the reaction mixture does not affect the nature of the products and the principal materials obtained, 146 and 147, (Table 19) probably arise by radical coupling.113)... 

Heathcock and Dugger examined the enolate derived from methyl 3-methylcrotonate (equation 29). When the aldol reaction with benzaldehyde is carried out at -70 C and quenched at this temperature, diastereomeric aldols (12) and (13) are formed in a ratio of 3 2. However, if the aldolate is warmed to 15 C prior to work-up, lactone (14 80%) and hydroxy ester (15 12%) are produced. These results con-... 

E-Methyl cinnamate, E-methyl crotonate, and methyl 3-methylcrotonate are unusual in that they undergo multiple addition of dichlorocarbene when subjected to phase transfer conditions [53]. A detailed study of this reaction has resulted in evidence for an initial cyclopropanation followed by a series of dehydrochlorinations and trichloro-methyl anion additions. The resulting tetrachlorospiropentanes which result from this complex sequence are shown in equations 2.34—2.36. Note that in these cases, there is no electron releasing group on the same carbon as the Michael activating substituent. 

Figure 6 and 7. Surface grafting of polyethylene (PE) and polypropylene (PP) films with acrylic acid (AA), methacrylic acid (MAA), crotonic acid (CA), tiglic acid (TA), 3-methylcrotonic acid (3-MCA) and a-methyl cinnamic acid (a-MCA), measured by absorption of visible light after grafting for 2 min. with vapor phase method and dipping in aqueous solution of crystal violet. 

Ethyl mercaptan, e20 Ethyl 3-methylcrotonate, el 21 Ethyl methyl ketone, b393 Ethyl 1-methylnipecotate, el 77 Ethyl 2-methyl-4-oxo-2-cyclohexene-1 carboxylate, c9... 

Vinylic bromine can be replaced fairly easily without reduction of the double bond. This is a characteristic difference from hydrogenolysis of vinylic chlorine and especially fluorine. Catalytic hydrogenation of ethyl a-methyl-3-bromocrotonate resulted in replacement of bromine and formation of ethyl a-methylcrotonate (equation 15). In 14-bromocodeinone (9), replacement of bromine occurs with a double bond shift to give neopinone (10 equation 16).4... 

Methylcrotonylglycinuria 3-Methylcrotonic acid, 3-methylcrotonyl-glycine, 3-hydroxypropionic, 2-methyl-citric, 3-hydroxy-3-methylbutanoic... 

In the first example27, the biotransformation of ethyl 4,4-dimethoxy-3-methylcrotonate with baker s yeast involves acetal hydrolysis and aldehyde reduction, as well as the enantiose-lective hydrogenation of the double bond. The resulting saturated hydroxy ester can be readily converted to (S)-3-methyl-y-butyrolactone by distillation of the raw extract with trace amounts of 4-toluenesulfonic acid. 

Binapacryl (29) is a compound with an action weaker than that of dinocap, and was initially also used as an acaricide. Its structural basis is dinoseb (28), which is an active substance with herbicidal properties. Binapacryl is formed by (he esterification of dinoseb with 3-methylcrotonic acid chloride, its chemical composition being 4,6-dinitro-2-jec-butylphenyl-3-methyl crotonate. 

E.27) (E.27) 2-Butenoic acid, 2-methyl, ( )-, (E)-2-methylbut-2-enoic acid, tiglic acid, r/wrv-tiglic acid, 2,3-dimethylacrylic acid, ( )-2-methylcrotonic acid 80-59-l] FEMA 3599 undefined stereochemistry... 

F.45) 2-Butenoic acid, 3-methyl-, ethyl ester, ethyl 3-methylbut-2-enoate, ethyl 3-methylcrotonate, ethyl 3,3-dimethylacrylate, ethyl isobutenoate, ethyl senecioate [638-10-81... 

Binapacryl. 3-Methyl-2-butenoic acid 2-(i-meth-ylpropyl)-4,6-dinitrophenyl ester 3-methylcrotonic acid 2-seC butyl-4,6-dinitrophenyi ester 2-sec-butyl-4,6-dinitro-phenyi 3,3-dimethylacrylate 2-sec-butyl-4,6-dinitrophenyl 3-methyl-2-butenoate 2 sec-butyl-4,6-dinilrophenyl 3-methylcrotonate 2 -see-butyl-4,6-dinitrophenyl senecioate 3,3-dimethylacrylic acid 2-sec-butyl-4,6-dinitrophenyl es. ter 4,6-dinitro-2-sec-butylphenyl P,P-dimethylacrylate 3-methyl-2-butenoic acid 2-sec-butyl-4,6-diniirophenyl ester dinoseb methacrylate senecioic aeid 2-sec-butyl-4,6-dinitrophenyl ester ENT 25793 HOE 2784 Acricid Am-box Endosan Morocide Niagara 9044. mol... 

Benzyl 2-methylcrotonate Benzyl trans-2-methyl crotonate. See Benzyl tiglate Benzyl methyl disulfide. See Methyl benzyl disulfide... 

CAS 7785-66-2 EINECS/ELINCS 232-086-2 Synonyms 2-Butenoic acid, 2-methyi-, n-butyi ester, (E)- Butyl (E)-2-methyl-2-butenoate trans-Butyl 2-methylcrotonate n-Butyl tigiate... 

CAS 61792-12-9 EINECS/ELINCS 263-215-0 Synonyms Cinnamyl 2-methylcrotonate 3-Phenylallyl 2-methylcrotonate 3-Phenyl-2-propenyl (E)-2-methyl-2-butenoate... 

Citronellyl 3-methylcrotonate CAS 20770-40-5 EINECS/ELINCS 244-019-4 Synonyms Citronellyl senecioate 3,7-Dimethyl-6-octenyl trans-3-methyl-2-butenoate Properties Flash pt. (CC) > 130 C Toxicology TSCA listed Uses Fragrance in cosmetics Manuf./Distrib. Grau Aromatics http //www.grau-aromatics.de Citronellyl nitrile... 

Dimethyl-6-octenyl trans-3-methyl-2-butenoate. See Citronellyl 3-methylcrotonate... 

CAS 638-10-8 EINECS/ELINCS 211-319-1 Synonyms 2-Butenoic acid, 3-methyl-, ethyl ester Crotonic acid, 3-methyl-, ethyl ester Ethyl dimethylacrylate Ethyl 3,3-dimethylacrylate Ethyl p,p-dimethylacrylate Ethyl isobutenoate Ethyl isopropylideneacetate Ethyl 3-methyl-2-butenoate Ethyl 3-methylcrotonate Ethyl p-methylcrotonate... 

Ethyl trans-2-methyl-2-butenoate Ethyl a-methylcrotonate Ethyl (E)-2-methylcrotonate (E)-2-Methyl-2-butenoic acid ethyi ester Tigic acid, ethyi ester... 

Synonyms Isobutyl cis-2-methyl-2-butenoate Isobutyl cis-a-methylcrotonate 2-Methylpropyl (Z)-2-methyl-2-butenoate Methylpropyl 2-methylisocrotonate... 

CAS 61692-84-0 EINECS/ELINCS 262-908-5 Synonyms 2-Methylpropyl (E)-2-methyl-2-butenoate 2-Methylpropyl 2-methylcrotonate Tiglic acid isobutyl ester... 

Isopropyl 2-methylcrotonate Isopropyl a-methyl crotonate Isopropyl a-methyl crotonic acid. See Isopropyl tiglate... 

Methyl 2-methylcrotonate Methyl (E)-2-methylcrotonate. See Methyl tiglate 1-Methyl-1-(4-methyl-3-cyclohexen-1-yl) ethyl butanoate Methyl methylcyclohexenyl ethyl butrate 1-Methyl-1-(4-methyl-3-cyclohexen-1-yl) ethyl butyrate. See Terpinyl butyrate (Z)-1 -Methyl-1 -(4-methyl-3-cyclohexen-1 -yl) ethyl cinnamate. See Terpinyl cinnamate 1 -Methyl-1 -(4-methylcyclohex-3-enyl) ethyl ethanoate. See Terpinyl acetate 1-Methyl-1-(4-methylcyclohex-3-enyl) ethyl methanoate. See Terpinyl formate... 

Methyl (E)-2-methyl-2-butenoic acid Methyl 2-methylcrotonate Methyl (E)-2-methylcrotonate Tigic acid methyl ester... 

Synonyms Benzyl carbinyl tiglate 2-Methyl-but-2-enoic acid phenethyl ester Phenethyl 2-methylcrotonate Phenylethyl (2E)-2-methyl-2-butenoate Phenylethyl-o-methylbutenoate Phenylethyl tiglate 2-Phenylethyl tiglate Classification Aromatic ester Empirical C13H16O2... 

The bark of this tree yielded ivorine, C26H44O5N (mp 159° [aj — 43°), which on treatment with methanol-hydrogen chloride gave the methyl ester of cassaic acid and methylaminoethanol. The acid esterifying the secondary hydroxyl was shown to be j8-methylcrotonic (Me2C = CH-Cl2H) and hence ivorine is XXXVI (86). 

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