63314-79-4

Upstream product

• 1352757-62-0 C₇H₁₀Cl₂O 
• 1352757-64-2 (R)-3-methylhept-5-yn-1-ol 
• 1352757-65-3 C₈H₁₂O 
• 1394157-04-0 (R)-3-methylhept-5-ynoic acid 
• 61898-56-4 (S)-4-methyltetrahydro-2H-pyran-2-one 
• 19013-37-7 dimethyl 3-methylglutarate 
• 63473-60-9 (R)-3-methylpentanedioic acid monomethyl ester 
• 69221-99-4 dodec-10-yn-1-ol 
• 86252-60-0 12-bromo-dodec-2-yne 
• 21890-10-8 3-methylcyclopentadecane-1,5-dione 
• 73125-89-0 14-methyl-16-oxabicyclo[10.3.1]hexadec-1⁽¹⁵⁾-ene 
• 101144-62-1 1-(trans-1-propenyl)-trans-cyclotridec-3-en-1-ol 
• 101164-87-8 1-(cis-1-propenyl)-trans-cyclotridec-3-en-1-ol 
• 21890-09-5 2,3,4,5,6,7,8,9,10,11,12,13-dodecahydro-2-methyl-1H-cyclopentacyclododecene 

Relevant academic research and scientific papers

METHOD FOR THE PRODUCTION OF MUSK FRAGRANCE INGREDIENT

A method for making intermediate compounds suitable for making muscenone, the compositions made by said methods, the various uses of said compositions, and enzyme variants useful in said methods.

PROCESS FOR PREPARING KETONES, IN PARTICULAR MACROCYCLIC KETONES

Ketones of the formula II where A is optionally alkyl-substituted C2-C12-alkanediyl, R1 and R2 are each, independently of one another, C1-C6-alkyl, or R1 and R2 together form optionally alkyl-substituted C3-C10-alkanediyl, and R3 is hydrogen or C1-C6-alkyl, are prepared by reacting a cyclic olefin of the formula I with dinitrogen monoxide to form the ketone of the formula II. The ketone of the formula II can be further hydrogenated to form the saturated ketone of the formula III. Macrocyclic ketones of the formula III, e.g. muscone, are sought after as fragrances.

An efficient route to the musk odorant (R,Z)-5-muscenone via base-metal-catalysis

Muscenone is a valuable perfume ingredient consisting of a mixture of the E- and Z-isomers of 1 in racemic form as the major constituents. Among them, it is the (R,Z)-isomer, which exhibits the most favorable musk character and by far the lowest threshold; for these superior olfactory properties, pure (R,Z)-1 has recently been commercialized too. We present an efficient route to this precious compound based on an iron-catalyzed cross coupling reaction, a molybdenum-catalyzed alkyne metathesis for the formation of the macrocyclic ring, and a nickel-catalyzed semi-hydrogenation.

(+)-(R,Z)-5-Muscenone and (-)-(R)-Muscone by enantioselective aldol reaction and grob fragmentation

(+)-(R,Z)-5-Muscenone ((R)-1) was synthesized by an enantioselective aldol reaction, catalyzed by new ephedrine-type Ti reagents (up to 70% enantiomeric excess). Substrate-directed diastereoselective reduction of the aldol product and Grob fragmentation of the tosylate of the resultant 1,3-diol afforded (+)-1. This approach also gave access to (-)-(R,E)-5-muscenone and (-)-(R)-muscone.

Cyclopropanated macrocyclic ketones and lactones

The present invention is directed to novel cyclopropanated macrocyclic ketone and lactone compounds of the general formula wherein X is an atom or a functional group selected from the group consisting of O, N, S, CH, or CH2; wherein Y is a straight or branched hydrocarbon moiety consisting of 1 to 20 carbon atoms; wherein W is a straight or branched hydrocarbon moiety of consisting of 1 to 20 carbon atoms; and wherein O is an oxygen atom; and the use of these novel compounds in creating fragrances, and scents in items such as perfumes, colognes and personal care products.

Cyclopropylcarbinyl radicals as three-carbon insertion units: Easy synthesis of C-15 macrocyclic ketones by three-carbon ring expansion

Thermal isomerization of cyclic 3-cyclopropyl ketones under FVP conditions at 620°C provides a new and convenient route to δ,ε-unsaturated cycloalkanones. The synthetic potential of this novel three-carbon ring expansion has been demonstrated by the synthesis of (±)-muscone from inexpensive C-12 starting material.

An efficient enantioselective synthesis of (+)-(R,Z)-5-muscenone and (-)-(R)-muscone - An example of a kinetic resolution and enantioconvergent transformation

An efficient catalytic kinetic resolution by CBS reduction and an original enantioconvergent transformation involving a PdII-catalyzed position-selective cyclization are the key steps for the synthesis of the exceptional musk odorant (R,Z)-5-muscenone [(R)-1] and (R)-muscone [(R)-3]. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Synthesis of (R)- and (S)- muscone

(R)-(-)-Muscone (3-methylcyclopentadecanone, 1) the key perfumery component isolated from the male musk deer, Moschus moschiferus,* was synthesized from the easily available chiral building block, (R)-3-tert-butoxycarbonyl-2- methylpropanoic acid (2), by employing ring-closing olefin metathesis (RCM). Antipode (+)-1 was also synthesized in a similar manner from tert-butyl (S)-3-methoxycarbonylbutanoate (10). *(a) Walbaum, H. J. J. Prakt. Chem., 73, 488 (1906); (b) Ruzicka, L., Further considerations on the constitution of muscone. Helv. Chim. Acta, 9, 715, 1008-1017 (1926).

Substituent Control of Sigmatropic Periselectivity: Application to the Synthesis of (+/-)-Muscone

The thermal and anionic rearrangements of trans-1-vinylcyclotridec-3-en-1-ol compounds substituted in the α and β vinyl positions have been examined to determine whether the substituents can be used to control the periselectivity.For the anionic rearrangements, trimethylsilyl groups were found to be unsuitable, and terminal vinyl methyl or isopropyl groups did not provide a useful selectivity.Under thermal conditions, either a terminal trimethylsilyl or methyl gave high periselective control favoring the 1,3-shift siloxy Cope ring expansion relative to the 3,3-shift.This was used in a new synthesis of muscone.

Substituent Control of Periselectivity: Application to the Synthesis of (+/-)-Muscone

The thermal, -shift siloxy-Cope, ring expansion is shown to be highly favoured relative to the -shift for the large-ring system required for the synthesis of muscone.