586-68-5

Upstream product

• 177698-19-0 Beta-pinene 
• 80-56-8 Pinene 
• 586-62-9 Terpinolene 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 586-63-0 isoterpinolene 
• 555-10-2 beta-phellandrene 
• 75658-59-2 C₁₆H₂₂N₂O₂S 
• 138-86-3 limonene. 
• 99-85-4 crithmene 
• 89-78-1 menthol 

Downstream Products

• 75600-79-2 (1S,7R,10R)-8-Isopropyl-10-methyl-4-((S)-1-phenyl-ethyl)-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione 
• 75600-79-2 (1R,7S,10S)-8-Isopropyl-10-methyl-4-((S)-1-phenyl-ethyl)-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 110-15-6 succinic acid 
• 99-87-6 4-methylisopropylbenzene 

Relevant academic research and scientific papers

Transition metal triflate catalyzed conversion of alcohols, ethers and esters to olefins

Herein, we report an efficient transition metal triflate catalyzed approach to convert biomass-based compounds, such as monoterpene alcohols, sugar alcohols, octyl acetate and tea tree oil, to their corresponding olefins in high yields. The reaction proceeds through C-O bond cleavage under solvent-free conditions, where the catalytic activity is determined by the oxophilicity and the Lewis acidity of the metal catalyst. In addition, we demonstrate how the oxygen containing functionality affects the formation of the olefins. Furthermore, the robustness of the used metal triflate catalysts, Fe(OTf)3 and Hf(OTf)4, is highlighted by their ability to convert an over 2400-fold excess of 2-octanol to octenes in high isolated yields.

CARBOCATIONIC TRANSFORMATIONS OF p-MENTHADIENES

The dynamics of the mutual carbocationic transformations were studied for the first time for the most important monoterpenoid hydrocarbons of the p-menthane series - β-limonene, limonene, terpinolene, isolimonene, isoterpinolene, α-terpinene, γ-terpinene, α-phellandrene, and β-phellandrene.The order of formation of the primary, secondary, tertiary, and other products of these transformations (with time) was established.On the basis of the obtained results a general scheme was formulated for the carbocationic transformations of p-menthadienes under the influence of acids.The fundamental possibility of using these reactions for the partial synthesis of individual rare hydrocarbons of the p-menthane series was demonstrated.

Thermodynamics of the Isomerisation of the p-Menthadienes and the Additivity of the Properties of Cyclic Hydrocarbons

We have studied the equilibria and obtained the thermodynamic parameters for the isomerisation of nine p-menthadienes in the range 225-350 deg C.An approach has been proposed and shown to be effective for the additive calculation of the properties of aliphatic hydrocarbons: this is based on the introduction of additional effective characteristics for an atom which take into account its participation in the ring system of the molecule.

ISOMERIZATION EQUILIBRIUM OF THE p-MENTHADIENES IN THE VAPOR PHASE

The isomerization equilibrium between nine p-menthadienes has been studied in the vapor phase at 250 deg C and their equilibrium ratios have been determined.A method for the quantitative GLC analysis of mixtures of isomeric p-menthadienes has been developed.

TRANSFORMATIONS OF p-MENTHADIENES UNDER THE ACTION OF POTASSIUM tert-BUTANOLATE IN DIMETHYL SULFOXIDE

The products of the transformation of α- and γ-terpinenes, terpinolene, (+)-trans-isolimonene, and (+)-limonene under the action of potassium tert-butanolate in dimethyl sulfoxide contained - in addition to the α- and γ-terpinenes, isoterpinolene, p-mentha-3,8-diene and p-cymene found previously - terpinolene, α- and β-phellandrenes, p-mentha-2,4-diene (in total amount of 1-3percent), and polymers.Under these conditions, limonene is racemized.The primary products of the isomerization reaction have been identified.A supplementary scheme for the isomerization transformations of p-menthadienes is presented.

Synthesis of Optically Active Triazolinediones and Examination of Their Utility for Inducing Asymmetry in Diels-Alder Cycloaddition Reactions

(S)-(-)-α-Methylbenzylamine, dehydroabietylamine, and endo-bornylamine have been transformed into the optically pure triazolinediones via the respective isocyanates and urazoles.Their ability to discriminate between diastereomeric Diels-Alder transition states was determined in the case of two dienes, 2,4-p-menthadiene and α-phellandrene, which were prepared in racemic and optically active forms of known enantiomeric purity.Exhaustive cycloaddition to these dienes gave the needed pairs of adduct D reference points against which those obtained in the asymmetric induction studies could be compared.By this technique, simple plots of D vs. diastereomeric purity served to delineate not only the level of enantioselection but also the absolute configuration of the adducts.Due in part to their exceptionally high reactivity, the triazolinediones are not sufficiently selective to permit high levels of enantioselection.Rather, their usefulness lies in their ability to achieve nondestructive resolution of various nonobivously resolvable compounds.

Terpene hydroxysulfonic acids and corresponding hydroxysulfonate salts

Optically active terpene hydroxysulfonate salts are made by sulfonating an optically active terpene epoxide of the p-menthane family, with a sulfonating agent selected from a sulfite, a bisulfite, or a thiosulfate.