43020-12-8

Usage

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C13H11ClO2/c1-8(15)12-7-13(16-9(12)2)10-3-5-11(14)6-4-10/h3-7H,1-2H3

Upstream product

• 89201-19-4 3-acetyl-1-(4'-chlorophenyl)-2-pentene-1,4-dione 
• 208118-80-3 1-(4-chlorophenyl)ethenylacetamide 
• 1956-39-4 4-chloroacetophenone oxime 
• 4251-65-4 (4-chlorophenyl)acetaldehyde 
• 123-54-6 acetylacetone 
• 28321-09-7 1-chloro-4-(2,2-difluorovinyl)benzene 
• 99-91-2 para-chloroacetophenone 
• 18218-20-7 1-(4-chlorophenyl)-1-phenylethene 
• 133216-65-6 4-acetyl-6,6-bis(4-chlorophenyl)-3-methyl-1,2-dioxan-3-ol 

Downstream Products

• 89201-19-4 3-acetyl-1-(4'-chlorophenyl)-2-pentene-1,4-dione 

Relevant academic research and scientific papers

Auto-Tandem Catalysis-Induced Synthesis of Trisubstituted Furans through Domino Acid-Acid-Catalyzed Reaction of Aliphatic Aldehydes and 1,3-Dicarbonyl Compounds by using N-Bromosuccinimide as Oxidant

A simple aluminium(III) chloride-catalyzed synthesis of tri-substituted furans from aliphatic aldehydes and 1,3-dicarbonyl compounds was developed by using N-bromosuccinimide (NBS) as an oxidant. This method was effective for the synthesis of various furan derivatives. Some of the products were not accessible with the previously reported methods. Mechanically, this reaction involved an auto-tandem catalysis based on a newly reported acid-acid-catalyzed tandem reaction to ensure that furans were successfully synthesized. (Figure presented.).

By accompanies two fluorine olefin preparing multi-substituted furan derivatives

The invention relates to a method for preparation of a polysubstituted furan derivative, the method comprises the following main steps: in the presence of a copper salt and an oxyacid salt of an IA element in the element periodic table, gem-difluoroolefin

Copper-catalyzed coupling cyclization of gem -difluoroalkenes with activated methylene carbonyl compounds: Facile domino access to polysubstituted furans

A novel and efficient CuI-catalyzed synthesis of 2,3,5-trisubstituted furans was developed via coupling cyclization of gem-difluoroalkenes with active methylene carbonyl compounds such as 1,3-dicarbonyl compounds, acetoacetonitrile, and phenylsulfonylacet

Direct oxidative coupling of enamides and 1,3-dicarbonyl compounds: A facile and versatile approach to dihydrofurans, furans, pyrroles, and dicarbonyl enamides

An efficient manganese(III)-mediated oxidative coupling reaction between α-aryl enamides and 1,3-dicarbonyl compounds has been developed. A series of dihydrofurans and dicarbonyl enamides were synthesized in moderate to good yields. Moreover, these dihydrofurans could be readily transformed into the corresponding furans and pyrroles via the Paal-Knorr reaction.

Synthesis of polyfunctionalized furans from 3-acetyl-1-aryl-2-pentene-1,4-diones

The BF3-catalyzed cyclization of 3-acetyl-1-aryl-2-pentene-1,4-diones 1a-e in the presence of water in boiling tetrahydrofuran gave bis(3-acetyl-5-aryl-2-furyl)methanes 2a-e in 26-79% yields along with a small amount of 3-acetyl-5-aryl-2-methylfurans 3a-e. The exact structure of 2a was determined by X-ray crystallography. The use of a half volume of the solvent for the reaction of 1a resulted in the formation of 2,4-bis(3-acetyl-5-phenyl-2-furfuryl)-3-acetyl-5-phenylfuran (4) together with 2a and 3a. A similar reaction of 1a was carried out in the presence of 3-acetyl-5-(4-methylphenyl)-2-methylfuran (3d) to afford 4-(3-acetyl-5-phenyl-2-furfuryl)-3-acetyl-5-(4-methylphenyl)-2-methylfuran (5) in 49% yield. The BF3-catalyzed reaction of 1a with 2,4-pentanedione in dry tetrahydrofuran at 23°C gave 3-(3-acetyl-5-phenyl-2-furfuryl)-4-hydroxy-3-penten-2-one (6a) and 3-(3-acetyl-2-methyl-4-phenyl-5-furyl)-4-hydroxy-3-penten-2-one (7a) in 66 and 24% yields, respectively. The product distribution depended on the reaction temperature. A similar reaction of 1b-e also yielded the corresponding trisubstituted furans 6b-e and tetrasubstituted furans 7b-e in good yields. These results suggested the presence of the furfuryl carbocation intermediate A during the reaction. The one-pot synthesis of 6a and 7a was also achieved by a similar reaction using phenylglyoxal. The deoxygenation of 1a with triphenylphosphine gave 3a in 88% yield, while 1a was treated with concentrated hydrochloric acid to yield 3-acetyl-2-chloromethyl-5-phenylfuran (8) which was quantitatively transformed in ethanol into 3-acetyl-2-ethoxymethyl-5-phenylfuran (9) and in water into 3-acetyl-5-phenylfurfuryl alcohol (10), respectively. In addition, the Diels-Alder reaction of cyclopantadiene with 1a gave the corresponding [4+2] cycloaddition products 11 and 12.

Synthesis of 2,3,5-Trisubstituted Furans by the Acid-Catalyzed Decomposition of 1,2-Dioxan-3-ols

Thirteen new 2,3,5-trisubstituted furans were prepared by the acid-catalyzed decomposition of 6,6-disubstituted 1,2-dioxan-3-ols in 57-93percent yields.The reaction could be accounted for as the consequence of an oxygen-oxygen bond cleavage by acid and the migration of a phenyl group at the C-6 position followed by cyclization and elimination of a phenol.The migratory aptitude was in the order of 4-MeOC6H4- greater than 4-MeO6H4- greater than Ph- = 4-FC6H4- greater than 4-ClC6H4- = 4-BrC6H4- that was found from the competitive phenyl migration in the reaction of 1,2-dioxan-3-ols bearing two different substituents at the C-6 position.

Manganese(II and III)-Mediated Synthesis of Cyclic Peroxides from Alkenes, Active Methylene Compounds, and Molecular Oxygen

The reaction of 1,1-diphenylethene, 1,1-bis(4-chlorophenyl)ethene, 1,1-bis(4-methylphenyl)ethene, 1,1-bis(4-methoxyphenyl)ethene, and 1,1-bis(4-fluorophenyl)ethene with 2-methyl-1,3-cyclohexanedione, 2-methyl-1,3-cyclopentanedione, 2-acetylcyclohexanone, ethyl 2-acetyl-3-oxobutanoate, 3-methyl-2,4-pentanedione, 1,3-cyclohexanedione, and 2,4-pentanedione in the presence of Mn(OAc)2 and molecular oxygen yielded the corresponding cyclic peroxides in moderate-to-good yields.Similar reaction of 1,1-disubstituted alkenes with 1,3-cyclopentanedione in the presence of Mn(OAc)3 and molecular oxygen gave 2,2,9,9-tetraphenyloctahydro-3,4,7,8-tetraoxabenzindene-4a,6a-diols.Acid-catalyzed decomposition of 4-acetyl-6,6-diaryl-3-methyl-1,2-dioxan-3-ols yielded 3-acetyl-5-aryl-2-methylfurans in moderate yields.Treatment of the 4-acetyl-6,6-diaryl-3-methyl-1,2-dioxan-3-ols with alkali gave 6,6-diaryl-3-methyl-1,2-dioxan-3-ols which gave 1-aryl-1,4-pentanediones upon treatment with hydrochloric acid in acetic acid.The synthetic utility and mechanism of the reactions are discussed.