21890-10-8

Upstream product

• 65033-42-3 14-methyl-6,17,18-trioxatricyclo[10.3.2.1^1,12 ]octadecane 
• 21890-09-5 2,3,4,5,6,7,8,9,10,11,12,13-dodecahydro-2-methyl-1H-cyclopentacyclododecene 
• 65033-37-6 cis-u. trans-14-Methyl-c-1,12-epoxybicyclo<10.3.0>pentadec-r-13-yl-(p-toluolsulfonat) 
• 65033-37-6 t-14-Methyl-c-1,12-epoxybicyclo<10.3.0>pentadec-r-13-yl-(p-toluolsulfonat) 

Downstream Products

• 21944-94-5 (Z)-5-muscenone 
• 101151-17-1 (5E)-3-methylcyclopentadec-5-en-1-one 
• 63314-79-4 (3R,5Z)-3-methylcyclopentadec-5-enone 
• 63314-79-4 (3S,5Z)-3-methylcyclopentadec-5-enone 
• 63314-79-4 (-)-(R,E)-3-methyl-5-cyclopentadecen-1-one 
• 63314-79-4 (3S,5E)-3-methylcyclopentadec-5-enone 
• 73125-89-0 14-methyl-16-oxabicyclo[10.3.1]hexadec-1⁽¹⁵⁾-ene 
• 10403-00-6 (R)-3-methyl-1-cyclopentadecanone 
• 85037-96-3 3-methyl-5-hydroxycyclopentadecanone 

Relevant academic research and scientific papers

Enantioselective intramolecular aldol addition/dehydration reaction of a macrocyclic diketone: Synthesis of the musk odorants (R)-muscone and (R,Z)-5-muscenone

(Chemical Equation Presented) One hundred years after the first isolation of natural (R)-muscone [(R)-1], a short and efficient access to the outstanding odorants (R)-1 and (R,Z)-5-muscenone [(R)-2] has become possible thanks to an unprecedented, reversible intramolecular aldol addition/enantioselective dehydration (up to 76% ee; see scheme).

New practical synthesis of the exceptional musk odorants (R)-muscone and (R,Z)-5-muscenone

Herein we describe a short and practical synthesis of the exceptional musk odorants (R)-muscone and (R,Z)-5-muscenone from a readily available achiral macrocyclic diketone. The key step of the synthesis is the first sodium N-methylephedrate mediated enantioselective aldol condensation reaction (up to 76% ee). This new type of reaction proceeds via a dynamic kinetic resolution of an aldol intermediate.

SYNTHESIS OF 14-METHYL-16-OXABICYCLO[10.3.1]HEXADEC-12-ENE

Disclosed is a scalable process for preparation of 14-methyl-16-oxabicyclo[10.3.1]hexadec-12-ene (BCE), a key intermediate for manufacture of fragrance ingredient 3-methylcyclopentadecenone (MUSCENONE) and analogs through reaction of 3-Methyl-1,5-cyclopentadecanedione (MCPD) and analogs with a metal or metalloid alkoxide in high yield and purity.

Method for the preparation of compounds having a 16-oxabicyclo[10.3.1]pentadecene scaffold and the subsequent products thereof

The present invention relates to a method for preparing compounds having a 16-oxabicyclo[10.3.1]pentadecene skeleton, specifically 14-methyl-16-oxabicyclo[10.3.1]pentadecenes, and conversion products thereof.

PROCESS FOR PREPARING 3-METHYLCYCLOPENTADECANE-1,5-DIOL

The present invention relates to a process for preparing 3-methylcyclopentadecane-1,5-diol (I) by hydrogenolysis of 14-methyl-16,17,18-trioxatricyclo[10.3.2.1]octadecane (II). The invention further relates to a process for preparing 3-methylcyclopentadecane-1,5-diol is a macrocyclic diol that can serve as precursor for a macrocyclic odorant, such as muscone and muscenone.

METHOD FOR PRODUCING CYCLIC DIKETONE COMPOUND

Provided is a method for producing a compound represented by general formula (I) by oxidative cleavage of a compound of formula (II), which is a bicyclic tetrasubstituted olefin compound, using hydrogen peroxide. The method for producing a compound represented by general formula (I) includes a step of subjecting a compound represented by general formula (II) to oxidative cleavage using hydrogen peroxide in the presence of an acid catalyst or in the presence of a tungstic acid compound to obtain the compound represented by general formula (I): [In the formulae, formula -A1- (where the front bond denotes a bond that bonds with a carbon atom C1 while the back bond denotes a bond that bonds with a carbon atom C2) is an alkylene group having 2 to 6 carbon atoms that may have been substituted and that may further include an ether bond, an ester bond, a secondary amino group, a thioether group, or these, and formula -A2- (where the front bond denotes a bond that bonds with a carbon atom C1 while the back bond denotes a bond that bonds with a carbon atom C2) is an alkylene group having 4 to 10 carbon atoms that may have been substituted and that may further include an ether bond, an ester bond, a secondary amino group, a thioether group, or these.]

PROCESS FOR PREPARING A MACROCYCLIC DIKETONE

The present invention relates to a process for preparing a macrocyclic diketone compound of the formula (I), which comprises the oxidation of a bicycloolefine compound of the formula (II) with an oxidizing agent, formulae (I) (II) where in formulae (I) and (II) A is (CH2)n with n being an integer from 2 to 12, where two hydrogen atoms may be replaced by C1-C4-alkyl, in particular methyl, or two hydrogen atoms, which are bound to adjacent carbon atoms may be replaced by a fused 5- or 6-membered saturated carbocycle; B is (CH2)m with m being 1 or 2, where 1 or 2 hydrogen atoms may be replaced by C1-C4-alkyl, in particular methyl.

(+)-(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.

SUBSTITUTED CYCLOHEXANONES

The present invention relates to a cyclohexanone derivative of formula (I) in the form of any one of its isomers or mixture thereof. The invention concerns also the preparation and the use of said derivative. The invention's compound is a useful starting