2005-60-9

Upstream product

• 1189-09-9 methyl geranate 

Downstream Products

• 162460-46-0 (1S,2R,3R)-1-methyl-3-(1-methyl-1-triethylsiloxyethyl)-2-(2'-nitrophenylselanylmethyl)cyclopentane 
• 162460-45-9 (1'R,2'R,3'S)-2-<2'-(2''-nitrophenylselanylmethyl)-3'-methylcyclopentyl>propan-2-ol 

Relevant academic research and scientific papers

The Kinetics of Photochemical Deconjugation Reactions of Methyl Geranate

The photochemical transformations of methyl geranate are analyzed in terms of the depedence of quantum yield upon base, 1,2-dimethylimidazole, concentration.The dependence of quantum yield of deconjugated esters methyl (3Z)-3,7-dimethyl-3,6-octadienoate (12), methyl 3-methylene-7-methyl-6-octenoate (13), and methyl (3E)-3,7-dimethyl-3,6-octadienoate (14) and the ratio of (13)/(12) and (13)/(14) upon base concentration, as well as the dependence of the ratios (methyl 2-isopropenyl-5-methylcyclopentanecarboxylate (15): deconjugated ester) (10)/(12), (10)/(13) and (10)/(14) upon the reciprocal of the base concentration, are consistent with relative rate constant ratios for (sigmatropic shift)/(dienol deprotonation) for photodienols 15, (precursor of 13), 17 (precursor of 12) and 19 (precursor of 14), of 72, 1.0 and 85.

THE PHOTOCHEMISTRY OF METHYL GERANATE, A MODEL CHROMOPHORE FOR INSECT JUVENILE HORMONE ANALOGS

The irradiation of methyl geranate (3) in ether using 254 nm lamps produces methyl 5-methyl-2-isopropenyl-4-hexenoate (13), 1,6,6-trimethyl-endo-5-carbomethoxybicyclo-hexane (11), methyl 2-isopropenyl-5-methylcyclopentanecarboxylate (12) and methyl (3Z)-3,7-dimethyl-3,6-octadienoate (14).Photolysis run in water or in ether in the presence of base generates two additional dienes: methyl 3-methylene-7-methyl-6-octaenoate (16) and methyl (3E)-3,7-dimethyl-3,6-octadienoate (17).The photolysis of methyl (2E, 6E)-3,7-dimethyl-2,6-nonadienoate (4a) in ether procedures all Z/E isomers, 4a - 4d.