76576-48-2

Basic information

• Product Name: Thiophene, 2-(1-cyclohexen-1-yl)-
• CAS NO: 76576-48-2
• Molecular Formula: C10H12S
• Molecular Weight: 164.271
• Mol File: 76576-48-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Thiophene, 2-(1-cyclohexen-1-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Thiophene, 2-(1-cyclohexen-1-yl)-(76576-48-2)
• EPA Substance Registry System: Thiophene, 2-(1-cyclohexen-1-yl)-(76576-48-2)

Safety Data

• Hazardous Substances Data: 76576-48-2(Hazardous Substances Data)

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 
• 108-93-0 cyclohexanol 
• 17138-80-6 2-(1-hydroxycyclohexyl)thiophene 

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 
• 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 
• 19163-24-7 5-phenyl-2-thiophenecarboxylic acid 
• 29488-24-2 2-Bromo-5-phenyl-thiophene 

Relevant articles and documents

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 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

New mass Spectra. Mass Spectra of Some 2- and 3-Cycloalkenylfurans and -Cycloalkenylthiophenes and their Oxyderivatives

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