17138-80-6

Upstream product

• 188290-36-0 thiophene 
• 108-94-1 cyclohexanone 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 1003-09-4 2-bromothiophene 
• 108-93-0 cyclohexanol 
• 3437-95-4 2-Iodothiophene 

Downstream Products

• 139401-06-2 1-azido-1-(2-thienyl)cyclohexane 
• 65601-86-7 2-cyclohexylthiophene 
• 1546999-68-1 3,5-dibromo-2-cyclohexylthiophene 
• 1546999-72-7 3-bromo-2-cyclohexyl-5-phenylthiophene 
• 1546999-75-0 1,2-bis(2-cyclohexyl-5-phenyl-3-thienyl)perfluorocyclopentene 
• 1567323-59-4 1-(1,1-dioxo-2-cyclohexyl-5-phenyl-3-thienyl)-2-(2-cyclohexyl-5-phenyl-3-thienyl)perfluorocyclopentene 
• 825-55-8 2-phenylthiophene 
• 58267-91-7 5-(cyclohex-1-en-1-yl)thiophene-2-carbaldehyde 
• 76576-48-2 2-(cyclohex-1-en-1-yl)thiophene 
• 100133-00-4 1-(2-thienyl)cyclohexylamine 

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.

The Barbier-Grignard-Type Arylation of Ketones and Unexpected Cross-Coupling of Phenolic Ketones using Unactivated Aryl Bromides

A novel, highly versatile and efficient method has been developed for the Barbier-Grignard-type arylation of ketones and an unexpected cross-coupling of phenolic ketones was observed using unactivated bromides and magnesium in tetrahydrofuran/toluene at 96°C promoted by multicatalysts of cupric bromide (15 mol%), bismuth chloride (5 mol%) and silver bromide (10 mol%). The substituent and electronic effects on the reaction have been discussed. High yields of arylation and cross-coupling have been attained under mild conditions. A novel reasonable mechanism involving a quinone intermediate is proposed. The high chemical selectivity in the cross-coupling to the hydroxy group of phenolic ketones should help ketones find new applications.

Iodine-Promoted Metal-Free Aromatization: Synthesis of Biaryls, Oligo p-Phenylenes and A-Ring Modified Steroids

We describe efficient procedures based on the use of iodine for the synthesis of biaryls from arylcyclohexenols or arylcyclohexanols using sub-stoichiometric/catalytic iodine and dimethyl sulfoxide (DMSO) as oxidant. Heteroarylcyclohexanols also produced the corresponding biaryl products. It was proven that biphenyl can also be efficiently obtained when the quantity of iodine was reduced to 0.05 equiv. The method is compatible with different functional groups in the aromatic ring (either electron-donating or electron-withdrawing groups). For substrate scope, apart from cyclohexanone and cyclohexenone, some substituted cyclohexanones were also used to synthesize the starting arylcyclohexanols. The process was applied to the synthesis of oligo p-phenylenes and A-ring aromatized steroids, where the combined use of I2/DMSO not only provoked the necessary migration of the methyl group at C-10, but also further extended the conjugation.

Photophysical properties of thiophenes and 2,2′-bithiophenes containing alicyclic moieties

A series of novel 1-hydroxycycloalkyl- and cycloalkenylthiophenes (4a-4c, 4e, 6b, 6d, 6e) and bithiophenes (5a-5e, 7b-7e) were synthesized via Grignard reaction. The conditions control in the Grignard reaction allowed to obtain tertiary alcohols or cycloa

Alkyl substituent effects in photochemical and thermal reactions of photochromic thiophene-S,S-dioxidized diarylethenes

Thiophene-S,S-dioxidized diarylethenes introducing various alkyl groups at the reactive positions were newly synthesized. The diarylethenes showed reversible photochromism, whereas the photocycloreversion reaction was suppressed by thiophene-oxidation. Th

Methods and compositions for treating amyloid-related diseases

Methods, compounds, pharmaceutical compositions and kits are described for treating or preventing amyloid-related disease.

Phencyclidine derivatives, preparation method and pharmaceutical compositions containing same

The invention concerns novel phenylcyclidine derivatives with selective affinity for low affinity receptors, methods for preparing them, pharmaceutical compositions containing them and their use as protective agents for central or peripheral nervous system cells against acute or chronic degeneration, or as an anticonvulsant.

PCP receptor and dopamine uptake sites are discriminated by chiral TCP and BTCP derivatives of opposite configuration

3-Methylpiperidine derivatives of 1-piperidine (TCP) and 1-thiophenyl)cyclohexyl>piperidine (BTCP) were obtained in their racemic and homochiral forms.They have been tested for their affinity for the K receptor label

Synthesis and Anticonvulsant Activity of 1-Phenylcyclohexylamine Analogues

Thirty-eight analogues of 1-phenylcyclohexylamine (PCA), a phencyclidine (PCP) derivative, were examined for their activities in the mouse maximal electroshock (MES) seizure test and in a motor-toxicity assay.In addition, we determined the binding affinities of the compounds for PCP acceptor sites in rat brain membranes labeled with -1-piperidine.Many of the analogues were protective against MES seizures (ED50s of 4-41 mg/kg, ip) and all of these compounds caused motor toxicity.The potencies in the motor toxicity and MES seizure tests showed a moderate correlation with the affinities for PCP sites.Several analogues exhibited a greater separation of potencies in the motor toxicity and MES seizure tests than did the parent compound PCA.These were obtained by (i) 3-methylation of the cyclohexyl ring trans to the phenyl ring, (ii) methoxylation at the ortho position on the phenyl ring, and (iii) contraction of the cyclohexane ring to form the corresponding cyclopentane.

Use of 2-Thienyl, 2-Furyl, 5-Ethyl-2-furyl, and Protonated 4-Acetylphenyl Substituents in Carbon-14 Nuclear Magnetic Resonance Chemical Shift Correlations

The application of the tool of increasing electron demand has been extended by employing increased electron-withdrawing as well as electron-donating substituents.In combination with the electron-withdrawing 4-protonated acetylphenyl substituent and the el