92854-06-3

Usage

Type of compound

Synthetic organic compound

Uses

Intermediate in the synthesis of pharmaceuticals
Intermediate in the synthesis of agrochemicals
Intermediate in the synthesis of other organic compounds
Production of dyes and pigments

Potential applications

Antiviral and antifungal agent

Environmental and health hazards

Use and handling must be conducted with caution due to potential risks

Chemical structure

Contains a buta-1,3-diene backbone with two 4-chlorophenyl groups attached to the 1,1-positions

Upstream product

• 18925-10-5 allylzinc bromide 
• 90-98-2 4,4'-Dichlorobenzophenone 
• 106-95-6 allyl bromide 
• 106-39-8 bromochlorobenzene 
• 6640-25-1 4-chlorophenyl cyclopropyl ketone 
• 1730-25-2 allylmagnesium bromide 
• 708967-53-7 1,1-bis-(4-chloro-phenyl)-4-dimethylamino-butan-1-ol 
• 214116-83-3 di(4-chlorophenyl)methylenecyclopropane 
• 288611-69-8 4-Dimethylamino-1,1-bis-<4-chlor-phenyl>-buten-(1) 

Downstream Products

• 1556997-75-1 2-[2,2-Bis(4-chlorophenyl)ethenyl]-3,5-dihydro-5-methylfuro[3,2-c]quinolin-4(2H)-one 
• 1556998-02-7 2-[2,2-bis(4-chlorophenyl)ethenyl]-6,6-dimethyl-2,3,6,7-tetrahydrobenzofuran-4(5H)-one 
• 6958-90-3 1,6-diphenylhexane-3,4-dione 

Relevant academic research and scientific papers

Neodymium-Promoted Highly Selective Carbon-Carbon Double Bond Formation of Ketones with Allyl Halides in the Presence of Diethyl Phosphite

The carbon-carbon double bond formation via neodymium-mediated Barbier-type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported for the first time. The reaction is highly α-regioselective and was conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with feasible reaction conditions.

An Example of Ketone Olefination via Praseodymium-Mediated Barbier Reaction in the Presence of Diethyl Phosphite

The first example of carbon double-bond formation via praseodymium-mediated Barbier type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported. The reaction is highly α-regioselective and conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with practical reaction conditions.

Pd(0)-catalyzed cross-coupling of allyl halides with α-diazocarbonyl compounds or N-mesylhydrazones: Synthesis of 1,3-diene compounds

With palladium catalysis, allyl bromides or chlorides react with α-diazocarbonyl compounds or N-mesylhydrazones to afford 1,3-diene derivatives. The reaction represents a novel and efficient method for the synthesis of 1,3-butadiene derivatives. Mechanist

Palladium-catalyzed cross-coupling of cyclopropylmethyl N-tosylhydrazones with aromatic bromides: An easy access to multisubstituted 1,3-butadienes

Direct synthesis of 1,1-disubstitued 1,3-butadienes has been efficiently realized from the cross-coupling of cyclopropylmethyl N-tosylhydrazones with aromatic bromides by means of PdCl2(MeCN)2 as catalyst. 1,1,4-Trisubstitued 1,3-but

A novel ketone olefination via organozinc reagents in the presence of diphenyl phosphite

Carbonyl compounds react with organozinc reagents in the presence of diphenyl phosphite to give the corresponding olefins. A variety of 1,3-dienes and unsaturated esters were obtained in moderate to excellent yields under mild conditions. The Royal Society of Chemistry 2012.

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.

Palladium-catalyzed isomerization of methylenecyclopropanes in acetic acid

PD(PPh3)4-catalyzed isomerization of MCPs 1 in acetic acid proceeds smoothly at 80 °C in toluene to give the corresponding I-substituted or 1,1-disubstituted dienes 2 in good to excellent yields under mild conditions. The plausible mechanism has been disclosed on the basis of a deuterium-labeling experiment.