4,6-Dimethyl-1-hepten

H,O0X " h3ccoo- 3 fi-Acetoxy-17 fl-[5 l6-dimethyl-hepten-(3) yl-(2)]579-cyclo-6,lO-cyclo-9710-seco-a ndrostadien- (7,911) 50 4... 

Dimethyl-hepten-(6)-4d-(4)-acatat 2,139. 2.2.Dimethyt-3A1>hyl-penteii-(3)-oi-(l )-aoeta4... 

Dimethyl-hepten-(2) S ure-(7) 2, 464. ek.-Butyl-allyl-e8iiga uTe 2 II417. /J-lBOiuDylid n-butt s uTe 2, 464. gt-Isoamyl-crotonsauTe 2, 464. 

Niteoeat dea Limonraibydtochlorids 3, 86. CioH G10 2.6-Dimethyl.hepten.(S)-carbon< 8tnre-(3)-ohlorid 2 II419. 

Acid catalyzed dehydration of 2 2 dimethyl 1 hexanol gave a number of isomeric alkenes including 2 methyl 2 heptene as shown in the following formula... 

From a perfumery point of view, trace ingredients again play an important role in the typical aroma of citroneUa oil. In 1980, IFF chemists isolated and characterized two nonterpenic compounds, melonol (2,6-dimethyl-5-hepten-l-ol [4234-93-9]) and melonal (2,6-dimethyl-5-heptenal [106-72-9]) with interesting green-melon odors (10). Although neither of these had previously been reported in nature, melonal has been a product of commerce for a number of years. 

Many other compounds are presendy in use a 1993 database search showed 27 active ingredients in 212 products registered by the U.S. EPA for human use as repellents or feeding depressants, including octyl bicycloheptene dicarboxamide (A/-2-ethylhexylbicyclo[2.2.1]-5-hepten-2,3-dicarboxamide), dipropyl isocinchomeronate (2,5-pyridine dicarboxyhc acid, dipropyl ester), dimethyl phthalate, oil of citroneUa, cedarwood oil, pyrethrins, and pine tar oil (2). Repellent—toxicant or biting depressant systems are available which are reasonably comfortable for the user and can protect completely against a number of pests for an extended period of time (2). 

Abbreviations aapy, 2-acetamidopyridine Aik, alkyl AN, acetoniuile Ar, aryl Bu, butyl cod, 1,5-cyclooctadiene COE, cyclooctene COT, cyclooctatetraene Cp, cyclopentadienyl Cp , penta-methylcyclopentadienyl Cy, cyclohexyl DME, 1,2-dimethoxyethane DME, dimethylformamide DMSO, dimethyl sulfoxide dmpe, dimethylphosphinoethane dppe, diphenylphosphinoethane dppm, diphenylphosphinomethane dppp, diphenylphosphinopropane Et, ethyl Ec, feirocenyl ind, inda-zolyl Me, methyl Mes, mesitylene nb, norbomene orbicyclo[2.2.1]heptene nbd, 2,5-norbomadiene OTf, uiflate Ph, phenyl PPN, bis(triphenylphosphoranylidene)ammonium Pi , propyl py, pyridine pz, pyrazolate pz, substituted pyi azolate pz , 3,5-dimethylpyrazolate quin, quinolin-8-olate solv, solvent tfb, teti afluorobenzobaiTelene THE, tetrahydrofuran THT, tetrahydrothiophene tmeda, teti amethylethylenediamine Tol, tolyl Tp, HB(C3H3N2)3 Tp , HB(3,5-Me2C3HN2)3 Tp, substituted hydrotiis(pyrazol-l-yl)borate Ts, tosyl tz, 1,2,4-triazolate Vin, vinyl. 

Azetidines 19 and 21 resulted (81M12) from photocycloaddition of 1,3-dimethyl-6-azathymine 17 with 1-heptene. The reaction could also be extended to the irradiation of 17 with 2-heptene, cyclohexene, and 1-, 3-, or 4-methylcyclohexene to give 20 and 22, respectively (87MI2). Photocycloaddition of dihalomaleimides 23 with 18 gave tricyclic 24 (83AG156) (Scheme 6). 

A mixture of 23.4 g (39.3 mmol) of bis[(tributyl)tin] oxide and 11.6 g (81.7 mmol) of 4,6-dimethyl-l-hepten-4-ol is heated at 220 CC for 10 h in a three-necked flask equipped with a 12-cm Vigreux column, a condenser, a thermostat, and separating funnel. During this time a further 11.6 g (81.7 mmol) of 4,6-dimethyl-1-hcp-ten-4-ol are added dropwisc, and 4-methyl-2-pentanone (approx. 16 g) distilled out. The residue is distilled yield 11.5 g (88%) bp 92-93 °C/0.3 Torr. 

A matched pair combination of the above silylketene acetal and (/ ,if)-2,4-dimethyl-2-heptenal has been applied in a stereoselective synthesis of the C17-C25 fragment of zincophor-... 

Dimalone [bicyclo-(2.2.1)-5-heptene-2,3-dicarboxylic acid dimethyl ester] and Octa-cide 264 [the V-octyl imide of bicyclo-(2.2.1)-5-heptene-2,3-dicarboxylic acid] do produce a red color with an absorption maximum in the same region as that obtained in the analysis of Compound 118. However, because Dimalone is an insect repellent and Octacide 264 is a pyrethrum synergist, neither of these products is likely to be encountered in commercial mixtures of Compound 118. The response to the colorimetric test for Compound 118 of some chemicals commonly used for insect control is listed in Table V. 

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