5729-92-0

Upstream product

• 59121-74-3 (1S,2R,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol 
• 1195-31-9 (+)-p-menth-1-ene 
• 67-56-1 methanol 
• 75-65-0 tert-butyl alcohol 
• 125627-55-6 (1S,2S,4R)-4-isopropyl-1-methyl-2-phenylselenenylcyclohexan-1-ol 
• 61585-35-1 p-menth-1-ene 
• 1195-92-2 Limonene oxide 
• 138-86-3 limonene. 
• 1946-00-5 (1RS,2SR,4RS)-p-menth-8-ene-1,2-diol 
• 93861-30-4 (1S,2R,4R)-p-menthane-1,2,8-triol 

Downstream Products

• 499-70-7 methyl-2 isopropyl-5 cyclohexanone 
• 2102-60-5 (+/-)-3,5-dinitro-benzoic acid-(trans-p-menth-6-en-2-yl ester) 

Relevant academic research and scientific papers

Diastereo and enantioselective synthesis of 1,2-diols promoted by electrophilic selenium reagents

Here we report the first example in which the phenylseleno group is directly substituted by a hydroxy function. The reaction is promoted by the PhSeOSO3H generated "in situ" by oxidation of (PhSe)2 with (NH4)2S2O8 at reflux in a 3:1 mixture of MeCN-H2O. I

Synthesis of (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus, its racemate, (1R,4R)- and (1S,4S)-isomers

(S)-Perillyl alcohol was converted to (R)-cryptone (91.5-93% ee) in six steps, which was then treated with methyllithium to give (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus. The racemic pheromone was also prepared by methylation of (±)-cryptone. Both (1R,4R)- and (1S,4S)-isomers (98% ee) of the pheromone were synthesized from the enantiomers of dihydrolimonene oxide.

Ruthenium Tetroxide Oxidation of Alkenes. A More Complete Picture

The ruthenium tetroxide oxidation of some linear and cyclic alkenes, representatives of five substitution patterns, has been performed in acetone-water (5:1) solution at -70 deg C using stoichiometric ammounts of the oxidant.The main reaction products are 1,2-diols and/or α-ketols depending on the nature of the substrate little amounts of scission products, aldehydes and/or carboxylic acids, are also obtained.Generally 1,2-diols predominate over α-ketols except in the oxidation of (-)-α-pinene that afforded the α-ketol in 51percent yield while no trace of the corresponding 1,2-diol was detected.All reactions prceeded through the formation of unstable brownish precipitates, presumably the intermediate ruthenium (VI) esters, which easily decomposed during the work-up step.Results from oxidation of trans-7-tetradecene and cis and trans-11-tetradecenyl acetate indicated that the reaction was syn stereospecific.In some cases, 1,3-dioxolane products, formed by condensation of the 1,2-diol and the aldehyde materials, were also obtained among the reaction products.Their possible origin is briefly discussed.

Monoterpenediol insect repellents

An insect repellent comprising as an active ingredient a monoterpenediol compound having the formula, STR1 wherein R1, R2 and R3 have either one of the following definitions: (i) all of R1, R2 and R3 are hydrogen, (ii) R1 is hydrogen and R2 and R3, taken together, form a carbon-carbon single bond, or (iii) R2 is hydrogen, R1 and R3, taken together, form a carbon-carbon single bond, and the hydroxyl bonded to the carbon atom marked with an asterisk takes an α-configuration.