165874-36-2

Upstream product

• 17627-49-5 (–)-menthone 
• 10458-14-7 (2R,5S)-menthone 
• 2216-51-5 (-)-menthol 
• 62338-23-2 (2-isopropyl-5-methylcyclohexyloxy)trimethylsilane 
• 72020-06-5 2-(2-isopropyl-5-methylcyclohexyloxy)tetrahydro-2H-pyran 
• 546-88-3 acetylhydroxamic acid 
• 10458-14-7 Menthone 
• 94827-79-9 3-Chlor-3-nitroso-1-methyl-4-isopropyl-cyclohexan 
• 75-24-1 trimethylaluminum 
• 3391-87-5 l-menthone 
• 491-07-6 (+/-)-menthone 

Downstream Products

• 13559-68-7 1-Acetoxy-1-nitroso-2-isopropyl-5-methyl-cyclohexan 
• 16508-42-2 trimethyl-((1R)-neoisomenthyl)-ammonium; iodide 
• 160399-90-6 isomenthylamine 
• 33045-08-8 3-Nitroso-3-benzoyloxy-menthan 
• 33045-11-3 (1R,3R,5S)-3-chloro-3-nitro-menthane 
• 33185-22-7 3-Brom-3-nitroso-isomenthan 
• 33045-10-2 (+)-t-3-Chlor-c-3-nitroso-r-1-p-menthan 
• 133287-32-8 (S)-2-Amino-4-methyl-pentanoic acid ((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide 
• 137465-68-0 (2S,3S)-2-Amino-3-methyl-pentanoic acid ((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide 
• 133287-26-0 (S)-2-Amino-N-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-propionamide 
• 85081-39-6 (2S,trans)-perhydro-2-isopropyl-5-methylazepine 
• 33045-06-6 3-Brom-3-nitroso-menthan 
• 33044-98-3 (-)-c-3-Chlor-t-3-nitroso-r-1-p-menthan 
• 33059-60-8 3-Nitro-3-acetoxy-menthan 

Relevant academic research and scientific papers

Chiral palladium complexes with monoterpenoids oximes

Oximes of cis-caran-4-one, 3α- and 3β-hydroxycaran-4-ones, cis-verbanone, menthone, and 2β-hydroxybornan-3-one have been synthesized. The obtained oximes react with lithium tetrachloropalladate to give new chiral palladium complexes containing mono-or bid

Structural and in Vitro Functional Characterization of a Menthyl TRPM8 Antagonist Indicates Species-Dependent Regulation

TRPM8 antagonists derived from its cognate ligand, (-)-menthol, are underrepresented. We determine the absolute stereochemistry of a well-known TRPM8 antagonist, (-)-menthyl 1, using VCD and 2D NMR. We explore 1 for its antagonist effects of the human TRPM8 (hTRPM8) orthologue to uncover species-dependent inhibition versus rat channels. (-)-Menthyl 1 inhibits menthol- and icilin-evoked Ca2+ responses at hTRPM8 with IC50 values of 805 ± 200 nM and 1.8 ± 0.6 μM, respectively, while more potently inhibiting agonist responses at the rat orthologue (rTRPM8 IC50 (menthol) = 117 ± 18 nM, IC50 (icilin) = 521 ± 20 nM). Whole-cell patch-clamp recordings of hTRPM8 confirm the 1 inhibition of menthol-stimulated currents, with an IC50 of 700 ± 200 nM. We demonstrate that 1 possesses ≥400-fold selectivity for hTRPM8 versus hTRPA1/hTRPV1. (-)-menthyl 1 can be used as a novel chemical tool to study hTRPM8 pharmacology and differences in species commonly used in drug discovery.

Atypical and Asymmetric 1,3-P,N Ligands: Synthesis, Coordination and Catalytic Performance of Cycloiminophosphanes

Novel seven-membered cyclic imine-based 1,3-P,N ligands were obtained by capturing a Beckmann nitrilium ion intermediate generated in situ from cyclohexanone with benzotriazole, and then displacing it by a secondary phosphane under triflic acid promotion. These “cycloiminophosphanes” possess flexible non-isomerizable tetrahydroazepine rings with a high basicity; this sets them apart from previously reported iminophophanes. The donor strength of the ligands was investigated by using their P-κ1- and P,N-κ2-tungsten(0) carbonyl complexes, by determining the IR frequency of the trans-CO ligands. Complexes with [RhCp*Cl2]2 demonstrated the hemilability of the ligands, giving a dynamic equilibrium of κ1 and κ2 species; treatment with AgOTf gives full conversion to the κ2 complex. The potential for catalysis was shown in the RuII-catalyzed, solvent-free hydration of benzonitrile and the RuII- and IrI-catalyzed transfer hydrogenation of cyclohexanone in isopropanol. Finally, to enable access to asymmetric catalysts, chiral cycloiminophosphanes were prepared from l-menthone, as well as their P,N-κ2-RhIII and a P-κ1-RuII complexes.

Synthesis of nitrogen-containing monoterpenoids with antibacterial activity

Incorporation of the Beckmann rearrangement into the presented research resulted in the formation of nitrogen-containing terpenoid derivatives originating from naturally occurring compounds. Both starting monoterpenes and obtained derivatives were subjected to estimation of their antibacterial potential. In the presented study, Staphylococcus aureus was the most sensitive to examined compounds. The Minimal Inhibitory Concentration (MIC) experiments performed on S. aureus demonstrated that the (?)-menthone oxime (?)-8 and (+)-pulegone oxime (+)-13 had the best antibacterial activity among the tested derivatives and starting compounds. Their MIC90 value was 100 μg/mL. The obtained derivatives were also evaluated for their inhibitory activity against bacterial urease. Among the tested compounds, three active inhibitors were found–oxime 14 and lactams (?)-15 and 16 limited the activity of Sporosarcina pasteurii urease with Ki values of 174.3 μM, 43.0 μM and 4.6 μM, respectively. To our knowledge, derivative 16 is the most active antiureolytic lactam described to date.

Stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via a Beckmann rearrangement facilitated by diphenyl phosphorazidate

A novel method for the stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via the Beckmann rearrangement was developed using diphenyl phosphorazidate (DPPA) as both the oxime activator and azide source. Various ketoximes were transformed into the corresponding 1,5-disubstituted tetrazoles with exclusive trans-group migration and no E-Z isomerization of the ketoxime. This method enables the preparation of 1,5-disubstituted tetrazoles without using toxic or explosive azidation reagents.

MgFe2O4@SiO2-PrNH2/Pd/bimenthonoxime core-shell magnetic nanoparticles as a recyclable green catalyst for heterogeneous Suzuki cross-coupling in aqueous ethanol

Magnetically recoverable MgFe2O4@SiO2-PrNH2/Pd/bimenthonoxime nanoparticles were prepared and characterized by SEM, EDX, TEM, XRD, XPS, ICP, VSM and FT-IR. The nanocatalyst was used for Suzuki cross-coupling in

Synthesis and structural characterization for novel mixed-donor ligand palladium (II) based on graphene and oxime: its application as a highly stable and efficient recyclable catalyst

In this article, the palladium (II) mixed-ligand complex synthesized with reduced graphene oxides containing tetraethoxysilane and menthone oxime was used as an efficient solid catalyst for the Heck coupling reaction. To maintain stability and catalytic activity in the C–C bond reaction, graphene was considered due to the available surface as the solid support. Then, the structure of new heterogeneous catalyst was investigated by FT-IR, UV–Vis DRS, FE-SEM, EDX, AFM, XRD, ICP-OES, Raman, and TGA. The newly synthesized nanocatalyst have beneficial properties, including product’s easy separation, the shorter time to react, purity products (yield 79–99%), and easier work-up procedure. Furthermore, the catalyst was reused six times without significant degradation in catalytic activity and performance.

Tandem and Selective Conversion of Tetrahydropyranyl and Silyl Ethers to Oximes Catalyzed with Trichloroisocyanuric Acid

Direct and oxidative conversion of tetrahydropyranyl and silyl ethers to oximes is described using trichloroisocyanuric acid (TCCA) as a relatively stable and inexpensive oxidant surprisingly in a catalytic amount and hydroxylamine hydrochloride under solvent-free conditions. Oximes can be synthesized from these protected alcohols in the presence of some other functional groups with excellent chemoselectivity using the present tandem catalytic method.

Europium(III) triflate-catalyzed Trofimov synthesis of polyfunctionalized pyrroles

The synthesis of polyfunctionalized pyrroles by reaction of a ketoxime with dimethyl acetylenedicarboxylate using europium(III) triflate as the catalyst is described. Copyright

Synthesis of C 1-symmetric chiral secondary diamines and their applications in the asymmetric copper(II)-catalyzed Henry (Nitroaldol) reactions

A small library of C1-symmetric chiral diamines (L1-L9) was constructed via condensing exo-(-)-bornylamine or (+)-(1S,2S,5R)-menthylamine with various Cbz-protected amino acids. Among them, ligand L1/CuCl 2?2H2O complex (2.5 mol %) shows outstanding catalytic efficiency for Henry reaction between a variety of aldehydes and nitroalkanes to afford the expected products in high yields (up to 98%) with excellent enantioselectivities (up to 99%) and moderate to good diastereoselectivities (up to 90:10). This process is air-and moisture tolerant and has been applied to the synthesis of (S)-2-amino-1-(3,4-dimethoxyphenyl) ethanol (9), a key intermediate for (S)-epinephrine and (S)-norepinephrine. On the basis of HRMS and X-ray diffraction analysis of the L1/CuCl2 complex, a transition-state model was proposed to explain the origin of asymmetric induction. The low catalyst loading, excellent yields and enantioselectivities, inexpensive copper salt, and mild reaction conditions make our catalytic system to be practically useful.