928-68-7

Usage

Uses

Used in Pharmaceutical Industry:
6-METHYL-2-HEPTANONE is used as a synthetic intermediate for the production of antifungal agents, specifically in the synthesis of crassinervic acid analogs. These analogs exhibit potent antifungal properties and are effective against a wide range of fungal infections.
Additionally, 6-METHYL-2-HEPTANONE is utilized in the synthesis of BACE-1 inhibitors, which are compounds designed to treat Alzheimer's disease. BACE-1 inhibitors work by reducing the production of beta-amyloid peptides, a hallmark of Alzheimer's disease, and have shown promise in slowing down the progression of the disease.

Synthesis Reference(s)

Tetrahedron, 49, p. 8169, 1993 DOI: 10.1016/S0040-4020(01)88036-4

InChI:InChI=1/C8H16O/c1-7(2)5-4-6-8(3)9/h7H,4-6H2,1-3H3

Upstream product

• 857824-76-1 2-(4-methylpentyl)oxirane 
• 6874-06-2 3,7-dimethyl-oct-2-ene 
• 5026-76-6 6-methylhept-1-ene 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 2009-74-7 6-methyl-3-hepten-2-one 
• 5699-78-5 5-methylhexanoyl chloride 
• 18815-73-1 methylzinc iodide 
• 104728-05-4 (E)-6-methyl-4-hepten-2-one 
• 10225-31-7 3-(3-methyl-butyl)-pentane-2,4-dione 
• 80113-44-6 4,8-dimethyl-3-nonenoic acid 
• 604-35-3 Cholesteryl acetate 
• 32700-63-3 2,2,6-Trimethyltetrahydropyran 
• 16647-04-4 6-methylhepta-3,5-dien-2-one 
• 506-82-1 dimethylcadmium 

Downstream Products

• 84696-81-1 ethyl (±)-3-hydroxy-3,7-dimethyloctanoate 
• 108478-44-0 6-methylheptane-2-one (2,4-dinitrophenyl)hydrazone 
• 502-59-0 octamylamine 
• 87247-19-6 (S)-6-Methylheptan-2-ol 
• 543-82-8 1,5-dimethylhexylamine 
• 1604-26-8 hydrodehydrolinalool 
• 503-00-4 (1,5-dimethyl-hexyl)-methyl-amine 
• 108241-32-3 2,6,9,13-tetramethyl-tetradec-7-yne-6,9-diol 
• 101440-18-0 bis-(1,5-dimethyl-hexyl)-amine 
• 4730-22-7 6-methyl-2-heptanol 
• 61652-37-7 6-methyl-heptan-2-one semicarbazone 
• 689-66-7 6,10-dimethyl-undec-5-en-2-one 
• 7535-34-4 2-Methyl-6-hydrazinoheptan 
• 61285-51-6 gand) 

Relevant academic research and scientific papers

Tuning nano-nickel selectivity with tin in flow hydrogenation of 6-methyl-5-hepten-2-one by surface organometallic chemistry modification

Chemoselective flow hydrogenation of 6-methyl-5-hepten-2-one was performed over nano-nickel catalysts. The parent catalyst composed solely of nickel nanoparticles grafted on the polymeric resin exhibited high activity and selectivity towards C[dbnd]C bond saturation but its modification with small quantities of tin significantly increased its ability to perform C[dbnd]O bond hydrogenation. The post-synthetic modification of the parent catalyst was achieved by surface organometallic chemistry approach and performed in the same flow micro-reactor, which was used for the catalytic studies, providing a methodology for online modification of parent catalysts.

Study on the selective hydrogenation of isophorone

3,3,5-Trimethylcyclohexanone (TMCH) is an important pharmaceutical intermediate and organic solvent, which has important industrial significance. The selective hydrogenation of isophorone was studied over noble metal (Pd/C, Pt/C, Ir/C, Ru/C, Pd/SiO2, Pt/SiO2, Ir/SiO2, Ru/SiO2), and non-noble metal (RANEY Ni, RANEY Co, RANEY Cu, RANEY Fe, Ni/SiO2, Co/SiO2, Cu/SiO2, Fe/SiO2) catalysts and using solvent-free and solvent based synthesis. The results show that the solvent has an important effect on the selectivity of TMCH. The selective hydrogenation of isophorone to TMCH can be influenced by the tetrahydrofuran solvent. The conversion of isophorone is 100%, and the yield of 3,3,5-trimethylcyclohexanone is 98.1% under RANEY Ni and THF. The method was applied to the selective hydrogenation of isopropylidene acetone, benzylidene acetone and 6-methyl-5-ene-2-heptanone. The structures of the hydrogenation product target (4-methylpentan-2-one, 4-benzylbutan-2-one and 6-methyl-heptane-2-one) were characterized using 1H-NMR and 13C-NMR. The yields of 4-methylpentan-2-one, 4-benzylbutan-2-one and 6-methyl-heptane-2-one were 97.2%, 98.5% and 98.2%, respectively. The production cost can be reduced by using RANEY metal instead of noble metal palladium. This method has good application prospects. This journal is

Chemoselective Hydrogenation of Olefins Using a Nanostructured Nickel Catalyst

The selective hydrogenation of functionalized olefins is of great importance in the chemical and pharmaceutical industry. Here, we report on a nanostructured nickel catalyst that enables the selective hydrogenation of purely aliphatic and functionalized olefins under mild conditions. The earth-abundant metal catalyst allows the selective hydrogenation of sterically protected olefins and further tolerates functional groups such as carbonyls, esters, ethers and nitriles. The characterization of our catalyst revealed the formation of surface oxidized metallic nickel nanoparticles stabilized by a N-doped carbon layer on the active carbon support.

Base-free transfer hydrogenation of aryl-ketones, alkyl-ketones and alkenones catalyzed by an IrIIICp* complex bearing a triazenide ligand functionalized with pyrazole

An IrIIICp* complex (2) bearing a triazenide ligand functionalized with pyrazole was synthesized and fully characterized by spectroscopic methods and the structure confirmed by X-ray diffraction studies. The catalytic activity of 2 and the control complex 3, which lacks of pyrazole in its structure, was evaluated in the reduction of aryl-ketones, alkyl-ketones, α,β-unsaturated and γ,δ-unsaturated ketones. The catalytic system, using either 2 or 3, exhibited good to excellent selectivity when tested with ketones and alkenones at 90 °C in 2-propanol as hydrogen source under base-free conditions. Reactivity of 2 in 2-propanol and NaH gave a neutral metal hydride (4) while in the absence of base gave two major cationic hydrides species (5 and 6).

Tuning Nano-Nickel Catalyst Hydrogenation Aptitude by On-the-Fly Zirconium Doping

The effect of nano-Ni catalyst post-synthetic Zr-modification on hydrogenation reaction of 6-methyl-5-hepten-2-one was investigated in a fixed bed continuous-flow micro-reactor to produce fine chemicals. The catalytic performance revealed that Zr-doping achieved by surface organometallic chemistry approach modifies the natural aptitude of nickel to hydrogenate C=C bond, since the addition of small quantities of zirconium significantly increased the amount of unsaturated and saturated alcohols formed in 6-methyl-5-hepten-2-one hydrogenation. Quantum chemical calculations revealed a stronger interaction between Zr←O=C that promotes the formation of C=C semihydrogenation product and enhances the probability of complete hydrogenation. The on-the-fly strategy presented herein enables for rapid optimization and understanding of catalytic processes.

Rh(III)Cp? and Ir(III)Cp? Complexes of 1-[(4-Methyl)phenyl]-3-[(2-methyl-4′-R)imidazol-1-yl]triazenide (R = t-Bu or H): Synthesis, Structure, and Catalytic Activity

A series of iridium and rhodium complexes have been synthesized using as ligand a triazenide monofunctionalized with an imidazole substituent. Steric hindrance at the imidazole moiety induced differences in the coordination modes as well in the catalytic behavior of complexes 4-7. Complexes 4-7 were tested in the transfer hydrogenation of acetophenone and 5-alken-2-ones. The hydrogenation of either the double bond or the carbonyl group in 5-alken-2-ones, showed to be selective in the presence of 6, 7, and 10 and has a dependence on the presence or absence of base. Control experiments point out that the imidazole moiety in the structure of complexes 4-7 speeds-up the catalysis.

Method for selectively hydrogenating alpha, beta-unsaturated carbonyl compound by cobalt complex

The invention provides a method for selectively hydrogenating an alpha, beta-unsaturated carbonyl compound. The method for selectively hydrogenating the alpha, beta-unsaturated carbonyl compound comprises the steps that first, a cobalt metal precursor and a carbene ligand are coordinated in a solution to obtain a cobalt complex, and the cobalt complex selectively enables the alpha, beta-unsaturated carbonyl compound to be reduced into a corresponding saturated carbonyl compound in a hydrogen atmosphere under the activation of an activator. The method for selectively hydrogenating the alpha, beta-unsaturated carbonyl compound has the main advantages that cobalt is used as a catalyst, and metal cobalt is cheap and easy to obtain relative to noble metal such as palladium, ruthenium, osmium, iridium and platinum, and the catalyst cost is greatly reduced; secondly, the carbene ligand used in the method has the advantages of simple structure, low price, strong coordination ability with cobalt atoms compared with a commonly used phosphine ligand; and finally, the addition of the activator can further significantly increase the activity of the cobalt catalyst. The hydrogenation reaction condition is mild, the reaction rate is high, substantially no carbonyl hydrogenation side reaction occurs, and the carbonyl compound can be obtained in a high yield.

Phosphonate-Mediated Immobilization of Rhodium/Bipyridine Hydrogenation Catalysts

RhL2 complexes of phosphonate-derivatized 2,2′-bipyridine (bpy) ligands L were immobilized on titanium oxide particles generated in situ. Depending on the structure of the bipy ligand—number of tethers (1 or 2) to which the phosphonate end groups are attached and their location on the 2,2′-bipyridine backbone (4,4′-, 5,5′-, or 6,6′-positions)—the resulting supported catalysts showed comparable chemoselectivity but different kinetics for the hydrogenation of 6-methyl-5-hepten-2-one under hydrogen pressure. Characterization of the six supported catalysts suggested that the intrinsic geometry of each of the phosphonate-derivatized 2,2′-bipyridines leads to supported catalysts with different microstructures and different arrangements of the RhL2 species at the surface of the solid, which thereby affect their reactivity.

STABILIZATION OF ACTIVE METAL CATALYSTS AT METAL-ORGANIC FRAMEWORK NODES FOR HIGHLY EFFICIENT ORGANIC TRANSFORMATIONS

Metal-organic framework (MOFs) compositions based on post?synthetic metalation of secondary building unit (SBU) terminal or bridging OH or OH2 groups with metal precursors or other post-synthetic manipulations are described. The MOFs provide a versatile family of recyclable and reusable single-site solid catalysts for catalyzing a variety of asymmetric organic transformations, including the regioselective boryiation and siiylation of benzyiic C—H bonds, the hydrogenation of aikenes, imines, carbonyls, nitroarenes, and heterocycles, hydroboration, hydrophosphination, and cyclization reactions. The solid catalysts can also be integrated into a flow reactor or a supercritical fluid reactor.

The Synthesis of Certain Phomentrioloxin A Analogues and Their Evaluation as Herbicidal Agents

A series of 28 analogues of the phytotoxic geranylcyclohexentriol (-)-phomentrioloxin A (1) has been synthesized through cross-couplings of various enantiomerically pure haloconduritols or certain deoxygenated derivatives with either terminal alkynes or borylated alkenes. Some of these analogues display modest herbicidal activities, and physiological profiling studies suggest that analogue 4 inhibits photosystem II in isolated thylakoids in vitro.