76576-48-2

Upstream product

• 108-94-1 cyclohexanone 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 188290-36-0 thiophene 
• 1003-09-4 2-bromothiophene 
• 7790-86-5 cerium(III) chloride 
• 17138-80-6 2-(1-hydroxycyclohexyl)thiophene 
• 108-93-0 cyclohexanol 

Downstream Products

• 825-55-8 2-phenylthiophene 
• 56721-43-8 5-Thenoylpentanoic acid 
• 58267-91-7 5-(cyclohex-1-en-1-yl)thiophene-2-carbaldehyde 
• 29488-24-2 2-Bromo-5-phenyl-thiophene 
• 19163-24-7 5-phenyl-2-thiophenecarboxylic acid 
• 1378021-42-1 [3a,4,5,6,7,7a-hexahydro-2-methyl-7a-(2-thienyl)benzofuran-3-yl]phenylmethanone 
• 1378021-43-2 1-[3a,4,5,6,7,7a-hexahydro-2-phenyl-7a-(2-thienyl)benzofuran-3-yl]ethanone 

Relevant academic research and scientific papers

Diels-Alder/Ene Reactivities of 2-(1′-Cycloalkenyl)thiophenes and 2-(1′-Cycloalkenyl)benzo[ b]thiophenes with N-Phenylmaleimides: Role of Cycloalkene Ring Size on Benzothiophene and Dibenzothiophene Product Distributions

Scaffolds of thiophene and benzothiophene are the important class of bioactive compounds found abundant in nature. The Diels-Alder reactions of 2-(1′-cycloalkenyl)thiophenes and 2-(1′-cycloalkenyl)benzo[b]thiophenes having the alkene groups present in five-, six-, seven-, eight-, and twelve-membered rings with substituted N-phenylmaleimides are characterized. The size of the cycloalkene rings plays a critical role in dictating the product distributions of expected and isomerized Diels-Alder adducts. 2D NMR studies indicate that the isolated isomers for 2-(1′-cycloalkenyl)thiophenes having five-, six-, and seven-membered rings are aromatized benzothiophene products, whereas eight- and twelve-membered rings are un-rearranged adducts. In addition, the product of subsequent ene-reaction with the N-phenylmaleimide is isolated for the five- and six-membered ring cases. Interestingly, in the 2-(1′-cycloalkenyl)benzo[b]thiophene having five-, six-, seven-, eight-, and twelve-membered rings, the un-rearranged dibenzothiophene Diels-Alder adduct is isolated in every instance. Molecular mechanics and density functional theory (M06-2X and PBE0-D3) calculations are performed to understand the differential reactivity of the various dienes for both the initial Diels-Alder reaction and a possible, subsequent ene reaction.

A novel and efficient method for the olefination of carbonyl compounds with Grignard reagents in the presence of diethyl phosphite

The widely available carbonyl compounds react with Grignard reagents in the presence of diethyl phosphite to give the corresponding olefins in good to excellent yields: A range of conjugated dienes, terminal olefins, multisubstituted-alkenes and conjugated enynes could be readily obtained by the method in mild conditions.

A one-pot preparation of aryl- and heteroarylcycloalkenes: Application to the total synthesis of (±)-laurokamurene B

A general one-pot method has been developed for the preparation of various aryl- and heteroarylcycloalkenes. After lithiation of aryl and heteroaryl bromides followed by transmetalation with CeCl3, the organocerium addition to cycloalkanones proceeds clea

Arylation and vinylation of alkenes based on unusual sequential semipinacol rearrangement/Grob fragmentation of allylic alcohols

(Chemical Equation Presented) Alkenes can be stereoselectively arylated and vinylated without transition-metal catalyst under mild conditions through an interesting NBS-promoted semipinacol rearrangement and a subsequent unusual NaOH-mediated Grob fragmentation.