57685-12-8

Upstream product

• 116499-64-0 (R)-dihydrocarvone 
• 6485-40-1 (R)-Carvone 
• 138-86-3 limonene. 
• 109-99-9 tetrahydrofuran 
• 5989-27-5 D-limonene 
• 3792-53-8 2-methyl-5-(prop-1-en-2-yl)cyclohexanone 
• 38050-36-1 (1R,8Ξ)-2c,9-methoxyboranediyl-(1rH,4tH)-p-menthane 

Downstream Products

• 38339-60-5 2-((1R,4R)-4-Methyl-3-oxo-cyclohexyl)-propionic acid 
• 65648-48-8 (2R,5R)-2-Methyl-5-vinyl-cyclohexanone 
• 83994-32-5 optically inactive 2-oxo-p-menthan-9-oic acid methyl ester 
• 83994-35-8 2-(4-Methyl-5-oxo-cyclohex-3-enyl)-propionic acid methyl ester 
• 83994-33-6 2-(4-Bromo-4-methyl-3-oxo-cyclohexyl)-propionic acid methyl ester 
• 140860-23-7 (1S,2R,5R)-5-((R)-2-Hydroxy-1-methyl-ethyl)-2-methyl-cyclohexanol 
• 140860-25-9 (1S,2R,5R)-5-((S)-2-Hydroxy-1-methyl-ethyl)-2-methyl-cyclohexanol 
• 140860-28-2 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 2-((1R,3S,4R)-3-acetoxy-4-methyl-cyclohexyl)-propyl ester 
• 140860-30-6 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 2-((1R,4R)-4-methyl-3-oxo-cyclohexyl)-propyl ester 
• 140860-29-3 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 2-((1R,3S,4R)-3-hydroxy-4-methyl-cyclohexyl)-propyl ester 
• 140860-27-1 Acetic acid 2-((1R,4R)-4-methyl-3-oxo-cyclohexyl)-propyl ester 
• 140924-70-5 (R)-2-((1R,4R)-4-Methyl-3-oxo-cyclohexyl)-propionaldehyde 
• 140860-17-9 Acetic acid 2-((1R,3S,4R)-3-hydroxy-4-methyl-cyclohexyl)-propyl ester 
• 57685-13-9 9-hydroxycarbotanacetone diacetate 

Relevant academic research and scientific papers

New renewably-sourced polyesters from limonene-derived monomers

The functionalisation of limonene has enabled the synthesis of two renewably-sourced monomers for the formation of terpene-derived polyesters. Three methods for the synthesis of the novel hydroxy-acid 6 are reported and their green-credentials scrutinised through comparison of their sustainability-metrics. Step-growth homo-polymerisation of 6 is demonstrated to yield a low molecular weight (2.6 kDa) novel polyester with 100% of its carbon content originating from the terpene starting material. The corresponding diol 2 is shown to act as a co-monomer with a renewable diacid. The resultant polyesters display impressive Mns of up to 30 kDa with Tgs between -6 and 24 °C. These materials have been shown to depolymerise under basic conditions for reclamation of the diol monomer 2.

Selective hydroboration of alkenes and alkynes in the presence of aldehydes and ketones

The reactions of terminal alkenes in the presence of ketones or aldehydes with a variety of borane reagents have been investigated. It was found that the selective hydroboration of a terminal alkene in the presence of a ketone or an aldehyde is most efficient when dicyclohexylborane is used as the hydroborating agent. The hydroboration of olefinic ketones and olefinic aldehydes with dicyclohexylborane generates the corresponding hydroxyaldehydes and hydroxyketones in good yields after oxidation with sodium perborate. The hydroboration of alkynyl ketones and alkynyl aldehydes with dicyclohexylborane yields the corresponding olefinic carbonyl compounds after protonation, or dicarbonyl compounds after oxidation.

Selective hydroboration of terminal alkenes in the presence of aldehydes and ketones

The hydroboration of olefinic ketones and aldehydes with dicyclohexylborane gives the corresponding hydroxy aldehydes and ketones in good yields after oxidation with sodium perborate.

Stoichiometric Hydroboration-Oxidation Reaction of Monocyclic Monoterpenoids: A Mechanistic Approach

The stoichiometric studies on hydroboration-oxidation reactions of (-)-carvone have been carried out to gain an insight into the mechanism of formation of unusual products 2-oxo-p-menth-9-ols (IVb,c), p-menth-2,9-diols (Xa,b) and p-menth-1-en-9-ol (VII).Based on high resolution PMR spectral data, the stereochemistry of IVb,c and Xa,b has been deduced.Similiar studies have been extended to (+)-dihydrocarvone and (-)-carveol.