499-94-5

Upstream product

• 5989-54-8 (-)-(S)-limonene 
• 1124-24-9 1-methylene-4-isopropylcyclohexane 
• 5432-85-9 4-isopropyl-cyclohexanone 
• 5989-27-5 D-limonene 
• 151-50-8 potassium cyanide 
• 5055-99-2 (+)-(1S,2S,5S)-carvomenthyl tosylate 

Downstream Products

• 18406-91-2 7-(Trimethylsilyl)-Δ^1,2-p-menthene 
• 131246-72-5 10-amino-1-p-menthene 
• 90582-69-7 N-[trans-5-isopropyl-2-methylcyclohex-2-enyl]amine 
• 131246-71-4 4-methyl-N-(1-p-menthen-10-yl)benzenesulfonamide 
• 131321-62-5 N-trans-[5-isopropyl-2-methylcyclohex-2-enyl]toluenosulfonamide 
• 99-82-1 Menthane 
• 99-87-6 4-methylisopropylbenzene 
• 112068-29-8 (1R,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol 
• 53399-74-9 (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol 
• 1678-82-6 trans-1,4-menthane 
• 6069-98-3 cis-1-isopropyl-4-methyl-cyclohexane 
• 1217498-98-0 (S)-4-Isopropyl-1-methyl-cyclohexane-1,2-diol 
• 159846-98-7 (E)-(S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-methyl-hept-3-en-2-one 
• 159846-97-6 (S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-methyl-heptan-2-one 

Relevant academic research and scientific papers

Method for synthesizing bark beetle pheromone

The bark beetle pheromone is (1S, 4R) -4 - isopropyl -1 - methyl -2 -cyclohexene -1 - alcohol, and the synthetic method comprises the following steps: forming a clathrate compound with (S)- (-) - limonene and carrying out catalytic hydrogenation reaction

Cobalt-Catalyzed Desymmetric Isomerization of Exocyclic Olefins

Chiral cyclic olefins, 1-methylcyclohexenes, are versatile building blocks for the synthesis of pharmaceuticals and natural products. Despite the prevalence of these structural motifs, the development of efficient synthetic methods remains an unmet challenge. Herein we report a novel desymmetric isomerization of exocyclic olefins using a series of newly designed chiral cobalt catalysts, which enables a straightforward construction of chiral 1-methylcyclohexenes with diversified functionalities. The synthetic utility of this methodology is highlighted by a concise and enantioselective synthesis of a natural product, β-bisabolene. The versatility of the reaction products is further demonstrated by multifarious derivatizations.

Scalable Total Synthesis of (-)-Vinigrol

Vinigrol is a structurally and stereochemically complex natural product that displays various potent pharmacological activities, including the capability to modulate TNF-α. A new and efficient synthetic route toward this natural product has been developed to complete the asymmetric synthesis of (-)-vinigrol and provide over 600 mg of material, manifesting the power of macrocyclic stereocontrol and transannular Diels-Alder reaction.

Identification of an Asexual Reproduction Inducer of Phytopathogenic and Toxigenic Fusarium

Asexual and sexual reproduction are the most important biological events in the life cycle of phytopathogenic and toxigenic Fusarium and are responsible for disease epidemics. However, the signaling molecules which induce the asexual reproduction of Fusarium are unknown. Herein we describe the structure elucidation, including the absolute configuration, of Fusarium asexual reproduction inducer (FARI), a new sesquiterpene derivative, by spectroscopic analysis, total synthesis, and conidium-inducing assays of synthetic isomers. We have also uncovered the universality of FARI among Fusarium species. Moreover, a mechanism-of-action study suggested that the Gpmk1 and LaeA signaling pathways are required for conidium formation induced by FARI; conversely, the Mgv1 of mitogen-activated protein kinase is not involved in conidium formation. FARI exhibited conidium-inducing activity at an extremely low dose and high stereoselectivity, which may suggest the presence of a stereospecific target.

Microwave assisted bi-functional activation of β-bromo-tert-alcohols

Microwave-assisted dehydration-oxidation of β-bromo-tert-alcohols to afford 2,3-unsaturated ketones in good yield is reported. The reaction of substrates with DMSO in 1:1 ratio (w/v) is promoted by ZnS in a solvent-free condition. A concurrent bi-functional activation of trans-vicinal bromo- and hydroxyl groups with ZnS is elucidated. This is a new observation under microwave and applies to β-bromo-tert-alcohols derived from 1,4-disubstitued-1-cyclohexenes. It is very useful in the synthesis of 2,3-unsaturated ketones derived from monoterpenes which are valuable flavour compounds. [Figure not available: see fulltext.]

Selective carvone hydrogenation to dihydrocarvone over titania supported gold catalyst

Selective hydrogenation of natural carvone to industrially valuable dihydrocarvone was carried out at 100°C under hydrogen pressure over a 1.9wt.% Au/TiO2 catalyst. The gold catalyst has demonstrated high activity as well as stereo- and chemoselectivity in conjugated C=C double bond hydrogenation with predominant formation of trans-dihydrocarvone. The catalytic activity and trans-to cis-isomers ratio were shown to strongly depend on the solvent. In a range of C1 - C3 alcohol solvents both catalytic activity and trans-to cis-dihydrocarvone ratio increased following the order: 2-propanol a nearly complete carvone conversion (90%) after 13h in the case of methanol, with the trans-to cis-dihydrocarvone ratio being about 1.8. Based on the transition state theory a quantitative description of trans-to cis-dihydrocarvone ratio variations in different solvents was made.

Eco-friendly kinetic separation of trans-limonene and carvomenthene oxides

Kinetic separation of trans-limonene oxide and trans-carvomenthene oxide was achieved in high yield by selective ring opening of their cis-epoxides in the presence of InCl3 catalyst in water. Catalytic activity of InCl3 was conserved

Selective reduction of dienes/polyenes using sodium borohydride/catalytic ruthenium(III) in various liquid amide aqueous mixtures

An efficient method to effect selective reduction of several structurally diverse dienes and an unsymmetrical triene is reported. The reduction is facile at 0 °C in a liquid amide aqueous solution containing sodium borohydride in the presence of 15 mol % ruthenium(III) chloride. The chemoselectivity of the reaction is controlled by proper choice of the liquid amide solvent.

FRAGRANCES WITH NOTE OF LILY OF THE VALLEY

A compound of formula (I) is described and use thereof as fragrance, especially as lily-of-the-valley fragrance and/or as an agent for increasing the substantivity and/or the retention of a fragrance preparation and/or as a fixative.

Reduction of carbon-carbon double bonds using organocatalytically generated diimide

(Chemical Equation Presented) An efficient method has been developed for the reduction of carbon-carbon double bonds with diimide, catalytically generated in situ from hydrazine hydrate. The employed catalyst is prepared in one step from riboflavin (vitamin B2). Reactions are carried out in air and are a valuable alternative when metal-catalyzed hydrogenations are problematic.