22460-48-6

Usage

InChI:InChI=1/C16H30O/c1-15-12-10-8-6-4-2-3-5-7-9-11-13-16(17)14-15/h15H,2-14H2,1H3

Upstream product

• 101592-14-7 3-methylhexadecanedioic acid 
• 73125-86-7 (4E,8E)-14-Methyl-16-oxa-bicyclo[10.3.1]hexadeca-4,8,13-triene 
• 73125-90-3 14-methyl-16-oxabicyclo[10.3.1]hexadecane 
• 14751-55-4 14-methylbicyclo<10.3.0>pentadec-1(12)-en-13-one 
• 56345-01-8 (2E)-cyclopentadec-2-en-1-one 
• 15681-48-8 lithium dimethylcuprate 
• 21889-95-2 3-methylcyclopentadec-1-yn-5-one 
• 37013-26-6 1-Methylenpentadeca-5,9,13-trien-3-on 
• 36152-11-1 15-Methyl-16-thia-bicyclo[11.2.1]hexadeca-1⁽¹⁵⁾,13-dien-2-one 
• 18650-13-0 hexadecane-2,15-dione 
• 75-24-1 trimethylaluminum 
• 22442-02-0 (Z)-3-methylcyclopentadec-3-en-1-one 
• 41059-07-8 4-Methyl-2-oxocyclopentadecancarbonsaeure-methylester 
• 73453-97-1 8-Methyl-1,5-dithiaspiro<5.14>eicosane 

Downstream Products

• 58259-50-0 methylcyclopentadecane 
• 63975-98-4 (S)-muscone 
• 824402-15-5 (2R,3R,7R)-N,N'-dibenzyl-7-methyl-1,4-dioxa-spiro[4.14]nonadecane-2,3-dicarboxamide 

Relevant academic research and scientific papers

CHEMISTRY OF ORGANOSILICON COMPOUNDS CLXXXVIII. REACTION OF ORGANODISILANES WITH DIENES CATALYZED BY TRANSITION METAL COMPLEXES. PREPARATION OF 1,8-BIS(TRIMETHYLSILYL)OCTA-2,6-DIENE AND ITS USE IN THE SYNTHESIS OF dl-MUSCONE

Organodisilanes, Me3-nXnSiSiXnMe3-n (X = Cl and MeO, n = 0, 1, 2) undergo efficient 1:2 addition reactions with butadiene and isoprene in the presence of a catalytic amount of a suitable palladium complex.One of the products, the title compound, was used as a starting material for a short synthesis of dl-muscone.

Novel synthetic method for muscone

Muscone is a precious fragrant compound scarce in nature. Many attempts to synthesize this unique natural product have been carried out. In this work, a novel synthetic method for the preparation of muscone from 3-methyl-15- hydroxypentadecanoate is provided. Benzimidazolium salt was used as tetrahydrofolate coenzyme model at formic acid oxidation level and Grignard reagent as nucleophile to which a one-carbon unit was transferred. The biomimetic synthesis of muscone was successfully accomplished using the addition-hydrolysis reaction of benzimidazolium salt with the Grignard reagent. Copyright Taylor & Francis, Inc.

A SIMPLE AND FACILE SYNTHESYS OF d,1-MUSCONE

An efficient method for the synthesis of d,1-muscone has been developed.

Purification and Characterization of an Enone Reductase from Sporidiobolus salmonicolor TPU 2001 Reacting with Large Monocyclic Enones

We discovered a novel enone reductase from Sporidiobolus salmonicolor TPU 2001 (SsERD) and expressed the gene in Escherichia coli. The enzyme catalyzed the reduction of (E)-3-methylcyclopentadec-2-en-1-one (E-2), cyclopentadec-2-en-1-one (3), and cyclododec-2-en-1-one (4) to (S)-muscone (S-1), cyclopentadecan-1-one (5), and cyclododecan-1-one (6), respectively. The apparent Km and Vmax values for E-2 were estimated to be 4.9±0.4 μm and 100±1.4 nmol min?1 mg?1, respectively. The enzyme was specific to NADPH, and cysteine residues strongly affected the enzyme activity. The enzyme exhibited the highest activity at pH 8.0 and high stability in the pH range from 4.5 to 11.0. Using 10 mU of the enzyme, S-1 was synthesized from 0.1 mm E-2 with 94.8 % yield and 100 % enantiomeric excess by incubation at pH 7.0 and 30 °C for 60 min. We further successfully constructed an enone reductase with high specific activity by mutation of SsERD. The Y67A variant from SsERD exhibited 4.5 times higher specific activity and 3 times higher catalytic efficiency toward E-2. This is the first report of an enzyme catalyzing the reduction of carbon–carbon double bond of large monocyclic enones.

The chemistry of thiophene-based bis-(p-quinodimethanes): An approach to macrocycles

Bis-2,5-dimethylene-2,5-dihydrothiophenes have been generated in the gas-phase by flash vacuum pyrolysis (FVP) of diester precursors. These thiophene-based bis-(p-quinodimethanes) are shown to undergo reactions leading to macrocycles. The conversions are consistent with a mechanism involving cyclic diradical intermediates followed by disproportionation of the radical centers.

A New Synthesis of Muscone and Exaltone. The Enamine Approach of Ring-Enlargement Reaction

Key reaction in the synthesis of the title compounds in the treatment of the aldehydes 6 and 7 (obtained from 1) with a primary amine, e.g. pentylamine, in EtOH at room temperature.After stirring overnight, the products 8 and 9, respectively, are obtained in good yields.Both are enlarged by three ring members and can be transformed to Exalton (12) and (+/-)-muscone, (13), respectively.

METHOD FOR PRODUCING 3-METHYLCYCLOALKENONE COMPOUND

The present invention relates to a method for producing a 3-methylcycloalkenone compound and a method for producing muscone. In the presence of a zirconium oxide catalyst, a diketone represented by the following general formula (1): wherein in formula (1), n represents 8, 9, 10, 11 or 12, is subjected to a vapor-phase intramolecular condensation reaction, whereby a 3-methylcycloalkenone compound can be produced with high reaction efficiency. When a 3-methylcyclopentadecenone compound produced by this method is hydrogenated in a known manner, muscone can be produced efficiently.

Method for preparing chiral musk ketone

A method for preparing chiral muscone is provided. 3-methyl-cyclopentadecane-1,5-dione is adopted as an initial raw material, chiral rhodium and a Br nsted acid are adopted as catalysts, hydrogen is adopted as a reductant, and a chiral muscone product is synthesized in a one-pot manner through asymmetric hydrogenation, hydrogenolysis and other reactions. The method is short and simple in route, high in total yield, low in generation of three types of waste and suitable for industrial production of the chiral muscone.

Method for preparing L-muscone

The invention discloses a method for preparing L-muscone. The method comprises the following steps: (1) L-muscone in racemic muscone and a chiral hydroxybenzene compound generate L-enantiomer salt under laser irradiation; and (2) crystallization separation and hydrolysis are performed on the L-enantiomer salt to obtain a L-muscone product, wherein the step (1) is carried out in the presence of a Bronsted acid catalyst. Preferably, after hydrolysis in the step (2), separation, purification and other steps are carried out to obtain the L-muscone product. The raw material used in the method is the racemic muscone with a mature production process; batch production can be realized, diastereomer salifying resolution is carried out by adopting laser irradiation, the product selectivity is greatlyimproved, the method is green, pollution-free, and less in production of three wastes, the chiral hydroxybenzene compound is convenient to recover and reusable, the atom economy is high, the productselectivity is high, and the method is suitable for being used in the fields of biology, medical treatment, medicines, spices, cosmetics and the like.

Preparation method of musk ketone

The invention relates to a preparation method of muscone, which includes the steps of: 1) adding 1,2-diol supported on polystyrene resin, 3-methyl dienone, methylbenzene and pyridinium p-toluenesulfonate, stirring and heating the materials, cooling the materials to room temperature, and filtering the materials to produce a first ketal compound; 2) adding a first solvent and a catalyst, performingheating reflux until the reaction is finished, cooling a reaction product to room temperature and filtering the reaction product to produce a second ketal compound; 3) adding a first solvent and an acid solution, stirring the mixture until the reaction is finished, cooling a reaction product to room temperature, washing the reaction product to separate a first organic layer, and performing normalpressure recovery to the solvent in the first organic layer to collect a first ketene compound; 4) adding an alcohol solution and a metal catalyst into a reaction bottle, repeatedly replacing gas in the reaction bottle with N2 and H2, and performing a reaction at normal temperature and under normal pressure, and when the reaction is finished, performing filtration and pressure reduced rectification to obtain the muscone. The preparation method is simple in technical process and low in cost, and allows industrial large-scale production.