33184-20-2

Basic information

• Product Name: 3-phenyl-4H-furo<3,2-c><1>benzopyran-4-one
• Synonyms: 3-phenyl-4H-furo<3,2-c><1>benzopyran-4-one
• CAS NO: 33184-20-2
• Molecular Weight: 262.265
• Mol File: 33184-20-2.mol

Chemical Properties

• CAS DataBase Reference: 3-phenyl-4H-furo<3,2-c><1>benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-4H-furo<3,2-c><1>benzopyran-4-one(33184-20-2)
• EPA Substance Registry System: 3-phenyl-4H-furo<3,2-c><1>benzopyran-4-one(33184-20-2)

Safety Data

• Hazardous Substances Data: 33184-20-2(Hazardous Substances Data)

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 58502-69-5 β-chloro-β-nitrostyrene 
• 133116-26-4 2,3-dihydro-2-nitro-3-phenyl-4H-furo<3,2-c><1>benzopyran-4-one 
• 4438-85-1 3H-chromene-2,4-dione 
• 102-96-5 (2-nitroethenyl)benzene 
• 70-11-1 α-bromoacetophenone 
• 118-93-4 o-hydroxyacetophenone 
• 81263-52-7 4-(2-oxo-2-phenylethoxy)-2H-1-benzopyran-2-one 
• 4636-16-2 iodoacetophenone 
• 98-86-2 acetophenone 
• 613-91-2 acetophenone oxime 
• 19433-17-1 acetophenone O-acetyloxime 
• 7257-94-5 1-phenyl-2-(p-tolylsulfonyloxy)ethanone 
• 108-95-2 phenol 

Downstream Products

• 19492-11-6 3-benzoyl-4-hydroxy-2H-chromen-2-one 

Relevant articles and documents

Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent

Cyclodehydration of α-phenoxy ketones promoted by Eaton’s reagent (phosphorus pentoxide–methanesulfonic acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare naphthofurans, furanocoumarins, benzothiophenes, and benzopyrans.

Iodine-mediated formal [3 + 2] annulation for synthesis of furocoumarin from oxime esters

A novel synthesis of furocoumarins was developed by a reaction between oxime esters and 4-hydroxycoumarins. The reaction was proposed to undergo radical mechanism mediated by iodine, a cheap and common laboratory reagent. Mechanistic studies showed the ke

A new route to substituted furocoumarins via copper-catalyzed cyclization between 4-hydroxycoumarins and ketoximes

A new route to substituted furocoumarins via copper-catalyzed cyclization between 4-hydroxycoumarins and ketoximes was developed. CuBr2 exhibited higher activity than other copper salts, affording the desired furocoumarins in high yields. The transformation proceeded readily in the absence of stoichiometric external oxidants. The significance of this synthetic strategy would be (1) the easily available starting materials; (2) low cost catalyst CuBr2; and (3) being without stoichiometric external oxidants. This protocol is complementary to previous approaches in the synthesis of substituted furocoumarins.

Copper-catalyzed radical/radical cross-coupling of ketoxime carboxylates with 4-hydroxycoumarins: A novel synthesis of furo[3,2-c]-coumarins

A novel and efficient strategy for the synthesis of furo[3,2-c]coumarins has been developed via copper-catalyzed radical/radical cross-coupling of ketoxime carboxylates with 4-hydroxycoumarins. This redox-neutral reaction allows smooth and selective synthesis of 2-substituted, 3-substituted, 2,3-disubstituted and 2,3-fused polycyclic furo[3,2-c]coumarins.

Metal-Free Synthesis of Furocoumarins: An Approach via Iodine-Promoted One-Pot Cyclization between 4-Hydroxycoumarins and Acetophenones

A transition metal-free approach was developed to achieve substituted furocoumarins via an iodine-promoted one-pot cyclization between 4-hydroxycoumarins and acetophenones. High yields of furocoumarins were achieved in the presence of NH4OAc as

Microwave-assisted synthesis and antifungal activity of novel fused Osthole derivatives

Based on the microwave-assisted synthetic protocol developed in our previous work, we have synthesized a series of novel furo[3,2-c]coumarins as fused Osthole derivatives, via the reaction of 4-hydroxycoumarins and β-ketoesters catalyzed by DMAP. All the target compounds were evaluated in?vitro for their antifungal activity against six phytopathogenic fungi, some compounds exhibited potential activity in the primary assays. Especially compounds 6c, 7b, 8b and 8c (shown in Fig.?1) were the most active ones, EC50values of these four compounds against Colletotrichum capsica, Botrytis cinerea and Rhizoctonia solani were further investigated. 6c was identified as the most promising candidate with the EC50value at 0.110?μM against Botrytis cinerea and 0.040?μM against Colletotrichum capsica, respectively, representing better antifungal activity than that of the commonly used fungicide Azoxystrobin.

Microwave-promoted Synthesis of Novel Fused Osthole Analogues

Osthole is a natural coumarin derivative and has a broad scope of biological activities. Two series of novel fused osthole analogues were designed, and synthesized through a highly efficient microwave-promoted synthetic protocol via the reaction of 4-hydroxycoumarins and β-ketoesters. The reaction conditions including solvent, catalyst, microwave power and irradiation time were also optimized. The pyrano[3,2-c]chromene-2,5-diones and furo[3,2-c]coumarins were obtained through two distinct intramolecular cyclization processes, and the proposed mechanism was also discussed.

[Hydroxy(tosyloxy)iodo]benzene in organic synthesis: A facile synthesis of furo[3,2-c]coumarins using-tosyloxyketones

Facile synthesis of furo[3,2-c]coumarins (2a-g) via cyclocondensation of 4-hydroxycoumarin and-tosyloxyketones (1a-g) is described. A plausible mechanism involving C-C bond formation followed by 5-exo-tet cyclization is suggested.

Synthesis and photooxygenation of furo[3,2-c]coumarin derivatives as antibacterial and DNA intercalating agent

Syntheses of 2,3-dimethyl-4H-furo[3,2-c]coumarin and 3-phenyl-4H-furo[3,2- c]coumarin as angular furocoumarins were carried out through Williamson reaction of 4-hydroxycoumarin with α-haloketones followed by cyclization. Photooxygenation of the synthesized furocoumarin derivatives was performed and the photoproducts were isolated and characterized. The affinity of 2,3-dimethyl-4H-furo[3,2-c]coumarin towards DNA and the antibacterial activity were evaluated and compared with 8-methoxypsoralen (8-MOP). Syntheses of 2,3-dimethyl-4H-furo[3,2-c]coumarin and 3-phenyl-4H-furo[3,2-c]coumarin as angular furocoumarins were carried out through Williamson reaction of 4-hydroxycoumarin with α-haloketones followed by cyclization. Photooxygenation of the synthesized furocoumarin derivatives was performed and the photoproducts were isolated and characterized. The affinity of 2,3-dimethyl-4H-furo[3,2-c]coumarin towards DNA and the antibacterial activity were evaluated and compared with 8-methoxypsoralen (8-MOP). Copyright

Regio and diastereoselective synthesis of functionalized 2,3-dihydrofuro[3,2-c]coumarins via a one-pot three-component reaction

An efficient and straightforward synthesis of furo[3,2-c]coumarins via the one-pot three-component condensation of aromatic aldehydes, 4-hydroxycoumarin and α-chloroketones in refluxing n-propanol is described. Pyridine or a mixture of AcOH and AcONH4 was used as a basic catalyst.