108235-80-9

Upstream product

• 16052-40-7 (-)-(1R,3R,4S)-4-isopropyl-1-methylcyclohexane-3-carboxylic acid 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 16052-42-9 (1R,2S,5R)-menthyl chloride 
• 63474-24-8 (1R,2S,5R)-(-)menthylmagnesium chloride 
• 2216-51-5 (-)-menthol 
• 663218-94-8 menthylformic acid 

Downstream Products

• 947258-18-6 C₁₈H₂₆N₂O₄ 
• 1160173-10-3 (1R,2S,5R)-2-isopropyl-5-methyl-N-(3-(o-tolyloxy)propyl)cyclohexane-carboxamide 
• 27373-99-5 (1R)-2t-isopropyl-5c-methyl-cyclohexane-r-carboxylic acid amide 
• 1221279-85-1 menthyl vinyl ketone 
• 108340-97-2 meso-α,α,α,α-tetrakis<2-<(p-menth-3-ylcarbonyl)amino>phenyl>-porphyrin 
• 68489-14-5 WS-5 

Relevant academic research and scientific papers

Method for preparing menthane carboxamide by taking L-menthol as raw material

The invention relates to a method for preparing menthane carboxamide by taking L-menthol as a raw material. The menthane carboxamide is prepared through the processes of chlorination, a Grignard reaction, acidification, acylating chlorination, amidation, distillation, recrystallization and the like in sequence. The process route is mature, has the advantages of operation management simplicity andsecurity risk reduction, during a chlorination process, lower-layer waste acid water is collected and reduced pressure distillation is carried out; H2O and HCl in the acid water are removed; recoveryof ZnCl2 is realized, reduced pressure distillation completion is realized, and a reagent, namely concentrated HCl, is added into the recovered ZnCl2; a ZnCl2/HCl saturated solution is prepared again,the L-menthol is added for chlorination reaction again, the steps are repeated, the waste acid water in the chlorination reaction can be repeatedly used, the production cost is saved, the wastewatertreatment cost is reduced, and the economic benefit is improved.

Ester ammonolysis reaction catalyst composition and preparation method of L-menthane carboxamide

The invention discloses an ester ammonolysis reaction catalyst composition and a preparation method of L-menthane carboxamide. The ester ammonolysis reaction catalyst comprises a catalyst and a ligand, wherein the catalyst is cuprous salt CuX, the ligand is a (R)-N, N, N, N-tetraalkyl binaphthylamine compound shown as the specification, wherein R1, R2, R3 and R4 are independently selected from thegroups shown as the specification. Menthyl chloride is used as the starting raw material in the method to react with metal magnesium to prepare menthyl magnesium chloride, then reaction with chloroformate with different substituent groups is carried out to obtain menthyl formate, and then ammonolysis under the catalysis of an ester ammonolysis catalyst composition is conducted to obtain the L-menthane carboxamide. The yield is improved, the production cost is reduced, the optical purity is high, and environmental protection and no wastewater discharge are realized.

SYNTHESIS OF ARYL CYCLOHEXANE CARBOXAMIDE DERIVATIVES USEFUL AS SENSATES IN CONSUMER PRODUCTS

Synthesis methods to produce a series of carboxamides built off of an (S)-2-amino acid backbone or an (R)-2-amino acid backbone, depending upon the desired diastereomer of the end product.

Process for making neo-enriched p-menthane compounds

A process for making neo-enriched p-menthane intermediates is disclosed. Lewis acid-catalyzed rearrangement of an oxaspiro compound provides an aldehyde mixture comprising normal (II) and neo (III) p-menthane-3-aldehydes: with the neo aldehyde (III) as the major product. The aldehyde mixture is readily oxidized to provide the corresponding carboxylic acids, and the acids are easily converted to a host of neo-enriched p-menthane esters or amides. The esters and amides are valuable as physiological coolants.

PROCESS FOR MAKING NEO-ENRICHED p-MENTHANE COMPOUNDS

A process for making neo-enriched p-menthane intermediates is disclosed. Lewis acid-catalyzed rearrangement of an oxaspiro compound provides an aldehyde mixture comprising normal (II) and neo (III) p-menthane-3-aldehydes: with the neo aldehyde (III) as the major product. The aldehyde mixture is readily oxidized to provide the corresponding carboxylic acids, and the acids are easily converted to a host of neo-enriched p-menthane esters or amides. The esters and amides are valuable as physiological coolants.

A novel type of optically active helical polymers: Synthesis and characterization of poly(α,β-unsaturated ketone)

New αβ-unsaturated ketone monomers, menthyl vinyl ketone (MVK), and 1-menthylbut-3-en-2-one (MBEK) were synthesized. The monomers were polymerized using butyllithium as an initiator. The polymer derived from MVK (poly-MVK) had a tremendous specific optical rotation α] 38525, which was as 32 times large as that of its monomer MVK. Poly-MVK was confirmed to keep a prevailing helicity of backbone in solution by means of comparing the specific optical rotation and the CD spectra with that of MVK and the model compound such as ethyl menthyl ketone (EMK) and n-hexyl menthyl ketone (n-HMK). This conclusion was also confirmed by the fact that the specific optical rotation and the CD signal intensity of poly-MBEK were not enough large dueto backbone flexibility caused by the effective isolation of the main chain from the bulky menthyl. The excess value of onehanded helicity of poly-MVK decreased with the increase of polymerization temperature.

Compositions and methods for the treatment of disease associated with Trp-p8 expression

Provided are small-molecule Trp-p8 modulators, including Trp-p8 agonists and Trp-p8 antagonists, and compositions comprising small-molecule Trp-p8 agonists as well as methods for identifying and characterizing novel small-molecule Trp-p8 modulators and methods for decreasing viability and/or inhibiting growth of Trp-p8 expressing cells, methods for activating Trp-p8-mediated cation influx, methods for stimulating apoptosis and/or necrosis, and related methods for the treatment of diseases, including cancers such as lung, breast, colon, and/or prostate cancers as well as other diseases, such as benign prostatic hyperplasia, that are associated with Trp-p8 expression.

N-arylsalkyl-carboxamide compositions and methods

N-(Substituted-aryl-alkyl)-cycloalkyl carboxamide compositions are disclosed that target molecular elements on sensory nerves and on secretory epithelia. Modulation of ion fluxes in neurons and epithelia inhibits the perception of itch, pain, discomfort from the skin. By acting on these targets, preferred embodiment compositions are useful for skin and sensory disorders, and, in the case of secretory epithelia, to retard cellular proliferation. These compounds are formulated as a topical or oral preparation with prolonged duration of action.

p-menthane-3-carboxaldehyde: A useful chiral auxiliary for the synthesis of chiral quaternary carbons of high enantiomeric purity

(+)- or (-)-p-Menthane-S-carboxaldehyde is made in two easy steps from (+)- or (-)-menthone, respectively. This auxiliary allows for the synthesis of carbonyl compounds bearing a α-chiral quaternary carbon. The flexibility, efficiency, and ease of use of

A stereodivergent approach to chiral nonracemic N-protected α,α-dialkylated amino acids

Menthyl carboxaldehyde is used as a chiral auxiliary to make quaternary amino acids of either configuration via a stereodivergent approach that includes an SN2′ displacement by a cuprate reagent and a Curtius rearrangement as key steps. Copyright