7-Hydroxy-5-decanone

According to the above procedure, oxidation of 1,5-decanediol (174 mg, 1 mmol) gave l-hydroxy-5-decanone, after column chromatography over silica gel (18 X 1.5 cm, 8 2 hexanes/ethyl acetate as eluent), 127 mg (isolated yield, 74%) as a colourless liquid analytical TLC on silica gel, 7 3 hexanes/ethyl acetate, / / = 0.17. 

Addition to a-aikoxy carbonyl compounds. n-Butylmagncsium bromide reacts stercosclcctivcly with protected, chiral a-hydroxy ketones. For example, reaction of the Grignard reagent with the MEM ether of 3-hydroxy-2-decanone in THF leads to the f/ireo-product [>95% isolated yield (equation I)]. The stereoselectivity is much lower when n-butyllilhium is used in addition the solvent plays an important role. Stereoselectivity is lower in C5H, 2, CH2CI2, and ether. A number of protective... 

Methyl lavender ketone (1-hydroxy-3-decanone) ECETOC (1995) NC 42.7 172.3... 

Decane is an alarm pheromone of the ant C. obscuripes866 Decanal (A95) is a pheromone component of larvae of C. pomonella (see Section 4.04.5.3.7),382 and is used by the red bug C. lectularius as an aggregation pheromone component.193 Males of a long-horned beetle, the coffee white stem borer Xylotrechus quadripes, a serious coffee pest in India, produce (S)-2-hydroxy-3-decanone (A96) as sex pheromone to attract female beetles.393 9-Oxo- (A97) and 9-hydroxydecanoic acid (A98) are the major sex pheromone components of females of the scoliid wasp Campsoscolia ciliata. Interestingly, the orchid Ophrys speculum also produces these compounds to attract males of Campsoscolia for pollination.394 ( )-4-Decanolide (A99)... 

The oxidation of alkylsilyl alkoxides has been extended to the preparation of a-hydroxy ketones from alkenylsilanes. Thus, 5-decenyltrimethylsilane was treated with meta-chloroperbenzoic acid and the resulting a-silyl epoxide oxidized with hydrogen peroxide in the presence of fluoride ion to give 6-hydroxy-5-decanone in 88% yield145 (equation 149). 

Gingerol. (S)-5-Hydroxy-l-(4-hydroxy-.i-methoxyphenyl)-3-decanone. Cl7H3404 mol wt 294.38. C... 

Gtngerol [6-gingerol, 5-hydroxy-l-(4-hydroxy-3-me-thoxyphenyl)-3-decanone]. 

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