3-Methyl-2-nonanone

MIBK is a flammable, water-white Hquid that boils at 116°C. It is sparingly soluble in water, but is miscible with common organic solvents. It forms an a2eotrope with water as shown in Table 2. Condensation of MIBK with another methyl ketone can produce ketones containing 9—15 carbons. For example, condensation with acetone produces diisobutyl ketone, and self-condensation of two MIBK molecules produces 2,6,8-trimethyl-4-nonanone [123-17-1]. Condensation with 2-ethylhexanal gives 1-tetradecanol (7-ethyl-2-methyl-4-undecanol), avaluable surfactant intermediate (58). 

That the situation is different for photochemical reactions is indicated by a particularly interesting recent study of some dialkylketones (239). In solution, 5-nonanone, 152, reacts photochemically to yield the cyclobutanol 153 and its isomer 154 in comparable amounts. Within the urea clathrate, however, 153 is the dominant product, with only traces of 154 being formed. The cyclobutanols analogous to 153, that is, having methyl and hydroxyl cis, also predominate in the urea-clathrate-mediated photocyclization of 2-hexanone and 2-undecanone. It might be expected that the bulky cyclobutane derivatives, which almost certainly cannot be crystallized in a urea clathrate, would also not be formed in such a clathrate. There are decomposition pathways (cleavage reaction 0 of the diradical intermediate that occur both in the clathrate and in solution. Nevertheless, the ring closure is a major pathway of reaction even in the clathrate. 

A total of 21 compounds present in the surface and cephalic extracts of the queen bumblebee, Bomhus terrestris, evoked responses in male antennae. These included saturated and unsaturated fatty acids, ethyl and methyl esters of the fatty acids, heptacosene, 2-nonanone, and geranyl geraniol. A blend of synthetic versions of these compounds elicited typical male mating behavior. 

Shaking of rac-3,4-dihydro-6-methyl-2-(l-oxopropyl)-2/f-pyran with baker s yeast resulted in initial formation of racemic 6-hydroxy-2,7-nonanedione and then by kinetic resolution/ diastereoselective reduction in the production of (67 ,7S)-6,7-dihydroxy-2-nonanone (2) where both relative and absolute configuration had to be determined (see p 470)134. 

In 1982, it was reported that an aliphatic ketone, on exposure to dimethyl (diazometh-yl)phosphonate, is converted to the corresponding cyclopentene. c.g., the conversion of 2-methyl-5-nonanone to cyclopentencs 1 and 226. 

The main volatile components isolated from bacuri shells using various isolation methods, such as steam distillation and supercritical CO2 extractions were (Z)-linalool oxide, ( )-linalool oxide, 2-pentanone, 2-nonanone, ds-hexenyl acetate, methyl dodecacanoate, and several hydrocarbons, including bisabolene [46]. 

By measuring standard compounds [5-nonanone, linalool, (-)-menthol, lin-alyl acetate, y-decalactone, ( )-a -ionone, 1-octanol, dodecane, methyl decano-... 

Females of the desert spider Agenelopsis aperta emit a volatile pheromone that attracts conspecihc males (Riechert and Singer, 1995). This pheromone was identified as 8-methyl-2-nonanone (1 Fig. 4.1), a previously unknown arthropod semio-chemical. It was found by headspace analysis and abdominal washings of females 2 weeks after their hnal molt, when they become sexually receptive it was absent in females of other age classes. The pheromone attracted males in a three-choice arena system at doses as low as 500 ng (Papke et al., 2001). Another female-specific ketone, 6-methyl-3-heptanone (2), was not attractive. Very low doses of 1 (10-9 mg/ml applied to a hlter paper placed in empty juvenile female webs) also induced courtship behavior in males (Papke et al., 2001). The normal behavioral sequence was followed, except for phases which required input from the female. The ED50 value (mean effective dose) of 1 was 5.5x 10-4 mg/ml hexane. In contrast, ketone 2 only induced a response in some males at unnaturally high concentrations... 

New total syntheses9 of azabicyclo[4.2.1]nonanone (10) have now been elaborated. The first synthesis started with 5-azidocyclo-oct-l-ene (7). Reduction and iV-methylation (via the urethane), followed by treatment of the secondary amine with hypobromous acid and with base, gave a mixture of 9-methyl-9-azabicyclo[4.2.1]nonan-2a-ol (8) and its 2/3-isomer (9), contaminated with some azabicyclo[3.3.1]nonane analogue cf. (18). The second synthesis starts with the monoepoxide from cyclo-octa-1,5-diene (11). Treatment with methylamine and... 

Hexanone, 2-heptanone, 2-octanone, 2-nonanone, 6-methyl-5-hepten-2-one, fenchone, carvone, acetophenone, 2-hydroxy-4,6-dimethoxy-5-methylacetophenone... 

Benzyl Alcohol trans-2-trans-4-Decadienal 2,4-Heptadienal Methyl Ethyl Ketone 2-Nonanone... 

Oxidation of 3-acetoxy-l-nonene (14) at 50 C gave a mixture of the methyl ketone (15) and 1-ace-toxy-3-nonanone (16) in 33% and 17% yields. The latter was formed by regioselective oxidation of 1-acetoxy-2-nonene, itself formed by the allylic rearrangement of (14) promoted by Pd ions (equation 11). 

H3C-CH=CH-CH2-NR2/ K-OR + H9C6-Hal/Li[AlHJ Cyclobntan 1 -Butyl-1 -hydroxy-2-methyl- E21a, 1130 (5-Nonanon/hv)... 

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