16130-53-3

Upstream product

• 583-03-9 1-Phenyl-1-pentanol 
• 1009-14-9 phenyl butyl ketone 
• 100-52-7 benzaldehyde 
• 138042-55-4 2-Chloro-1-phenyl-2-(toluene-4-sulfinyl)-pentan-1-ol 
• 138042-67-8 2-chloro-1-phenyl-2-(p-tolylsulfinyl)-1-pentanone 

Downstream Products

• 119492-87-4 2,5-diphenyl-3-propylfuran 
• 7642-18-4 (Z)-pent-1-en-1-ylbenzene 
• 16002-93-0 (E)-1-phenyl-1-pentene 

Relevant academic research and scientific papers

Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives

The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling.

Solvent-free preparation of α,α-dichloroketones with sulfuryl chloride

An efficient and facile method is reported for the synthesis of a series of α,α-dichloroketones. The direct dichlorination of methyl ketones and 1,3-dicarbonyls using an excess amount of sulfuryl chloride affords the corresponding gem-dichloro compounds in moderate to excellent yields. Moreover, the protocol features high yields, broad substrate scope, and simple reaction conditions without using any catalysts and solvents.

Domino Radical Addition/Oxidation Sequence with Photocatalysis: One-Pot Synthesis of Polysubstituted Furans from α-Chloro-Alkyl Ketones and Styrenes

A new domino reaction has been developed that allows the combination of styrenes and α-alkyl ketone radicals to afford a wide array of polysubstituted furans in good to excellent yields under mild and simple reaction conditions. The key to success of this novel protocol is the use of photocatalyst fac-Ir(ppy)3and oxidant K2S2O8. Mechanistic studies by a radical scavenger and photoluminescence quenching suggest that a radical addition/oxidation pathway is operable.

1-Haloalkyl Aryl Sulfoxides as Useful Agents in Synthesis of α-Halo Ketones: A New Synthesis of α-Halo Ketones, α-Halo α,β-Unsaturated Ketones, and α-Halo Cross Dienones from Aldehydes

α-Halo α-sulfinyl ketones were synthesized in two steps from 1-haloalkyl aryl sulfoxides and aldehydes in high yields.Desulfinylation of the α-halo α-sulfinyl ketones was performed with ethylmagnesium bromide in ether at low temperature to afford α-halo ketones via magnesium enolates in high yields.The magnesium enolate intermediates were trapped with various electrophiles such as deuterium oxide, ethyl chloroformate, and chlorotrimethylsilane.Trapping of the magnesium enolate intermediate with carbonyl compounds afforded a new type of the directed aldol reaction.Desulfi nylation of the sulfinyl group of the α-halo α-sulfinyl ketones under thermal conditions gave α-halo α,β-unsatureted ketones or α-halo cross dienones.

ETHYLMAGNESIUM BROMIDE MEDIATED DESULFINYLATION OF α-HALO-β-KETOSULFOXIDES GIVING α-HALOKETONES, AND TRAPPING OF THE MAGNESIUM ENOLATE INTERMEDIATE

Treatment of α-halo-β-ketosulfoxides with EtMgBr gives α-haloketones in high yields after protonation of the magnesium enolates.Trapping of the magnesium enolates with various electrophiles is also carried out.

One-pot Synthesis of α-chloroketones from Secondary Benzylic Alcohols Using m-Chloroperbenzoic Acid/HCl/DMF System

The one-pot reaction of the oxidation and chlorination of sec-benzylic alcohols by using m-CPBA/HCl/DMF system led to the corresponding α-chloroketones in good yields.

7,8,9,10-Tetrahydrothieno[3,2-e]pyrido[4,3-b]indole compounds and their anti-depressant use

The present invention relates to certain new 7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole compound, to a process for their production and to their use as agents which have an influence on the central nervous system. The ring system according to the invention has not hitherto been described in the literature.