116497-11-1

Basic information

• Product Name: (2E)-1-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-2-en-1-one
• Synonyms: (2E)-1-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-2-en-1-one
• CAS NO: 116497-11-1
• Molecular Weight: 192.301
• Mol File: 116497-11-1.mol

Chemical Properties

• CAS DataBase Reference: (2E)-1-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-2-en-1-one(116497-11-1)
• EPA Substance Registry System: (2E)-1-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-2-en-1-one(116497-11-1)

Safety Data

• Hazardous Substances Data: 116497-11-1(Hazardous Substances Data)

Upstream product

• 61899-98-7 2,6,6-trimethylcyclohex-2-en-1-ylidene ketene 
• 2622-05-1 allylmagnesium bromide 
• 151725-96-1 (S)-2,6,6-Trimethyl-cyclohex-2-enecarbothioic acid S-phenyl ester 
• 28102-24-1 (S)-α-damascol 
• 908297-89-2 (-)-(6S,9S)-7-oxo-α-dihydroionol acetate 
• 174198-90-4 [(S)-2,6,6-trimethylcyclohex-2-enyl]but-3-en-1-one 
• 57523-79-2 (2E,5E)-6,10-dimethyl-undeca-2,5,9-trien-4-one 
• 31089-90-4 1-(2',6',6'-trimethyl-2'-cyclohexenyl)-3-buten-1-one 
• 17522-32-6 (S)-dehydro-α-damascol 
• 134780-16-8 (R)-2,4,4-trimethyl-2-cyclohexen-1-ol 
• 13395-71-6 2,4,4-trimethyl-2-cyclohexenone 
• 815581-80-7 (RS)-1-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-3-en-1-ol 
• 815581-75-0 (1S,5R)-5-(hydroxymethyl)-4,6,6-trimethylcyclohex-3-enol 
• 86561-83-3 (S,E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol 

Downstream Products

• 143605-78-1 2,2-Dimethyl-propionic acid 3-benzyloxy-1-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-butyl ester 
• 143605-80-5 2,2-Dimethyl-propionic acid 3-oxo-1-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-butyl ester 
• 143605-79-2 2,2-Dimethyl-propionic acid 3-hydroxy-1-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-butyl ester 
• 143605-74-7 3-Benzyloxy-1-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-butan-1-ol 
• 14398-36-8 (3E)-4-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-3-en-2-one 
• 878665-16-8 (3RS)-hydroxy-[(1S)-(2,6,6-trimethylcyclohex-2-en-1-yl)]butan-1-one 
• 143605-73-6 3-Benzyloxy-1-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-butan-1-one 

Relevant articles and documents

Synthesis of the enantiomeric forms of α- and γ-damascone starting from commercial racemic α-ionone

A straightforward synthesis of both enantiomers of α- and γ-damascone is described. The title compounds were prepared by a divergent pathway starting from the enantiomeric forms of (6RS,7SR,9RS)-7-hydroxy-7,8-dihydro-α-ionol and of (6RS,7SR,9RS)-7-hydroxy

A simple and efficient highly enantioselective synthesis of α-ionone and α-damascone

An efficient highly enantioselective (ee ≥99%) synthesis of α-ionone and α-damascone is described. Both enantiomers of title compounds were synthesized through two straightforward pathways diverging from enantiopure (R)- or (S)-α-cyclogeraniol. These versatile building blocks were obtained by regioselective ZrCl4-promoted biomimetic cyclization of (6S)- or (6E)-(Z)-6,7-epoxygeraniol, respectively, followed by deoxygenation of the so formed secondary alcohol. The chiral information was encoded by a highly regioselecive Sharpless asymmetric dihydroxylation of inexpensive geranyl acetate.

APPLICATION OF BIOCHEMICAL METHODS IN ENANTIOSELECTIVE SYNTHESIS OF BIOACTIVE NATURAL PRODUCTS

Enzymes as well as yeasts were used in enantioselective syntheses of bioregulators such as hormones and semiochemicals.Lipases and esterases were employed in achieving optical resolution, conversion of meso-compounds to optically active compounds, and macrolactonization.Lactase effected glucosidation of a phenolic hydroxy ketone without any protection of the functional groups.Yeasts provided a variety of optically active hydroxy esters and ketones, which served as versatile non-racemic chiral building blocks.

Efficient Synthesis of Enantiomerically Pure α-Ionone from (R)- and (S)-α-Damascone

(R)- and (S)-α-ionone ((R)- and (S)-1, resp.) were prepared from (R)- and (S)-α-damascone ((R)- and (S)-3, resp.) without racemization in 48percent yield employing a new enone transposition.The described transposition is complementary to existing methods whose application is often prohibited by the structural requirements of the substrate.The now easily accessible α-ionones of desired absolute configuration are useful as chiral building blocks for terpenoid syntheses.

Alkenoyl-cyclohexadienes

New cycloaliphatic unsaturated ketones and their use as perfuming and odour-modifying agents in the manufacture of perfumes and perfumed products, and as flavouring and taste-modifying agents in the preparation of foodstuffs in general and imitation flavours for foodstuffs, beverages, animal feeds, pharmaceutical preparations and tobacco products. Methods for the preparation of said cycloaliphatic unsaturated ketones.