62452-63-5

Basic information

• Product Name: Naphtho[2,3-b]furan-4,9-dione, 2-phenyl-
• CAS NO: 62452-63-5
• Molecular Formula: C18H10O3
• Molecular Weight: 274.276
• Mol File: 62452-63-5.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: Naphtho[2,3-b]furan-4,9-dione, 2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Naphtho[2,3-b]furan-4,9-dione, 2-phenyl-(62452-63-5)
• EPA Substance Registry System: Naphtho[2,3-b]furan-4,9-dione, 2-phenyl-(62452-63-5)

Safety Data

• Hazardous Substances Data: 62452-63-5(Hazardous Substances Data)

Upstream product

• 75204-51-2 2-phenylnaphtho[1,2-b]furan-4,5-dione 
• 75204-49-8 ethyl 4,5-dioxo-3-phenyl-4,5-dihydronaphtho[1,2-b]furan-2-carboxylate 
• 127636-05-9 2-ethylthio-3-phenacyl-1,4-naphthoquinone 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 536-74-3 phenylacetylene 
• 35135-38-7 2-hydroxy-3-iodonaphthalene-1,4-dione 
• 139386-48-4 2,3-dihydro-2-phenylnaphtho<2,3-b>furan-4,9-dione 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 122-78-1 phenylacetaldehyde 
• 100-42-5 styrene 
• 105438-12-8 (E)-2-hydroxy-3-styrylnaphthalene-1,4-dione 
• 858019-89-3 2-(α,β-dibromo-phenethyl)-3-hydroxy-[1,4]naphthoquinone 
• 105438-12-8 2-hydroxy-3-styryl-[1,4]naphthoquinone 
• 16883-69-5 N-phenacylpyridinium bromide 

Downstream Products

• 59382-19-3 2-hydroxy-3-(2-phenyl-2-oxo)ethyl-1,4-naphthoquinone 
• 75204-51-2 2-phenylnaphtho[1,2-b]furan-4,5-dione 

Relevant articles and documents

Transition-Metal-Free One-Pot Synthesis of Naphthoquinonefuran Derivatives through Sequential Nucleophilic Substitution-Nucleophilic Addition Reaction

A transition-metal-free route for tandem one-pot synthesis of naphthoquinonefuran derivatives from 2-hydroxynaphthoquinones has been developed. The sequentially accomplished process comprises an intermolecular alkynylation of sp2-carbon at the 3 position of 2-hydroxynaphthoquinones with arylethynyl bromides, followed by a base-promoted intramolecular nucleophilic annulation reaction. A broad range of functional groups is compatible with this reaction, and diverse naphtho[2,3-b]furan-4,9-diones can be obtained with good yields and excellent regioselectivity.

Synthesis, anti-proliferative activity evaluation and 3D-QSAR study of naphthoquinone derivatives as potential anti-colorectal cancer agents

Colorectal cancer (CRC) is a disease with high incidence and mortality, constituting the fourth most common cause of death from cancer worldwide. Naphthoquinones are attractive compounds due to their biological and structural properties. In this work, 36 naphthoquinone derivatives were synthesized and their activity evaluated against HT-29 cells. Overall, high to moderate anti-proliferative activity was observed in most members of the series, with 15 compounds classified as active (1.73 50 2 = 0.99 and q2 = 0.625). This model allowed proposing five new compounds with two-fold higher theoretical anti-proliferative activity, which would be worthwhile to synthesize and evaluate. Further investigations will be needed to determine the mechanism involved in the effect of most active compounds which are potential candidates for new anticancer agents.

Synthesis of Stilbene-Quinone Hybrids through Heck Reactions in PEG-400

Styrenes were coupled with 3-iodolawsone in PEG-400 at 90 °C, leading stereoselectively to (E)-stilbene-quinone hybrids through Heck reactions. The best reaction conditions were found to be the use of NaOH (3 equiv) and 10 mol% of palladium acetate at 90 °C for 15 minutes. The chemical yields of the Heck reactions using styrenes with electron-withdrawing groups (65-98%) were greater than styrenes bearing electron-donating groups (7-32%) on the aromatic ring. In particular, the chemical yields of Heck reactions involving nitrostyrenes were the best ones observed.