42482-66-6

Upstream product

• 92631-38-4 (3R)-2,2,6-trimethyl-3-phenylthio-6-p-tetrahydropyran 
• 43161-11-1 5-iodo-2-methylpent-2-ene 
• 2270-59-9 1-bromo-4-methylpent-3-ene 
• 84375-03-1 2-Oxo-6-methylhept-5-enoic acid 
• 76729-59-4 6,6-Dimethyl-2-carboxy-5,6-dihydropyran 
• 76729-61-8 ethyl 6-methyl-2-oxohept-5-enoate 
• 630110-57-5 2-(2-hydroxymethyl-6,6-dimethyl-tetrahydro-pyran-2-yl)-5-methyl-phenol 
• 630110-53-1 6,6-dimethyl-5,6-dihydro-4H-pyran-2-carboxylic acid 2-iodo-5-methyl-phenyl ester 
• 833-85-2 5-(4-methylphenyl)-5-oxopentanoic acid 
• 42482-94-0 ethyl 5-(4-methylphenyl)-5-oxopentanoate 
• 1446350-97-5 3,4,5,6-tetrahydro-2,2-dimethyl-6-(4-methylphenyl)-6-[(phenylselanyl)methyl]-2H-pyran 
• 108-88-3 toluene 
• 108-55-4 glutaric anhydride, 
• 75-16-1 methylmagnesium bromide 

Relevant academic research and scientific papers

Reductive Alkylation of Alkenyl Acetates with Alkyl Bromides by Nickel Catalysis

Catalytic alkylation of stable alkenyl C?O electrophiles is synthetically appealing, but studies to date have typically focused on the reactions with alkyl Grignard reagents. We report herein a cross-electrophile reaction of alkenyl acetates with alkyl bromides. This work has enabled a new method for the synthesis of aliphatic alkenes from alkenyl acetates to be established that can be used to add more structural complexity and molecular diversity with enhanced functionality tolerance. The method allows for a gram-scale reaction and modification of biologically active molecules, and it affords access to useful building blocks. Preliminary mechanistic studies reveal that the NiI species plays an essential role for the success of the coupling of these two reactivity-mismatched electrophiles.

Electrochemical phenylselenoetherification as a key step in the synthesis of (±)-curcumene ether

Two variants of a new pathway for the synthesis of (±)-curcumene ether are described. The key steps in these procedures are intramolecular cyclizations of 6-methyl-2-(4-methylphenyl)hept-6-en-2-ol and 2-methyl-6-(4-methylphenyl)hept-6-en-2-ol by means of an electrochemically generated phenylselenyl cation. This synthetic approach provides significantly better yields than the previously reported protocols. Copyright

Synthesis of (+/-)-curcumene ether

A 9 step synthesis of (+/-)-curcumene ether is described starting from 5-bromo-2-methyl-2-pentene and 2-amino-5-methylphenol in 7% overall yield using an intramolecular Heck reaction as the key transformation to generate a stereogenic quaternary center.

Synthetic Studies on Aromatic Sesquiterpenoids: Synthesis of Curcumene Ether by Olefin Cyclisation

The acid-catalysed cyclisation of the olefinic β-hydroxy sulphides (15a) and (15b) gave 3-phenylthiocurcumene ether as a diastereoisomeric mixture together with 5,5-dimethyl-4-phenylthio-1-p-tolylcyclohex-1-ene (16) and 2-methyl-3-(1-methyl-1-phenylthioethyl)-2-p-tolylcyclobutan-1-ol (19).The diastereoisomers (17) and (18) were converted into curcumene ether (24).Treatment of the silyl enol ether (7) with benzenesulphenyl chloride yielded 5-phenylthiomethyl-2-tetrahydrofuran (8) and 5-chloro-1,6-bis(phenylthio)-1-p-tolylhexan-2-one (9). 1-p-Tolylhexane-2,5-dione (10) was also synthesised from (5) employing a palladium-catalysed oxidation, and this result constitutes a formal total synthesis of cuparene (11).