479-12-9

Basic information

• Product Name: 6H-Benzofuro[3,2-c][1]benzopyran-6-one
• Synonyms: 6H-Benzofuro[3,2-c][1]benzopyran-6-one;Coumestane;coumestan
• CAS NO: 479-12-9
• Molecular Formula: C₁₅H₈O₃
• Molecular Weight: 0
• Mol File: 479-12-9.mol

Chemical Properties

• Boiling Point: 417.2°C at 760 mmHg
• Flash Point: 206.1°C
• Appearance: /
• Density: 1.385g/cm³
• Vapor Pressure: 3.62E-07mmHg at 25°C
• Refractive Index: 1.696
• CAS DataBase Reference: 6H-Benzofuro[3,2-c][1]benzopyran-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6H-Benzofuro[3,2-c][1]benzopyran-6-one(479-12-9)
• EPA Substance Registry System: 6H-Benzofuro[3,2-c][1]benzopyran-6-one(479-12-9)

Safety Data

• Hazardous Substances Data: 479-12-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6H-Benzofuro[3,2-c][1]benzopyran-6-one is used as a pharmaceutical compound for its potential therapeutic properties. 6H-Benzofuro[3,2-c][1]benzopyran-6-one's unique structure allows it to interact with various biological targets, making it a promising candidate for the development of new drugs. Its specific application reasons include its ability to modulate cellular signaling pathways, inhibit tumor growth, and enhance the efficacy of conventional chemotherapeutic drugs.
Used in Drug Delivery Systems:
In the field of drug delivery, 6H-Benzofuro[3,2-c][1]benzopyran-6-one is used as a component in the development of novel drug delivery systems. These systems aim to improve the compound's delivery, bioavailability, and therapeutic outcomes by employing various organic and metallic nanoparticles as carriers. This approach can help overcome limitations associated with the compound's solubility, stability, and targeted delivery to specific cells or tissues.
Used in Chemical Research:
6H-Benzofuro[3,2-c][1]benzopyran-6-one is also used as a research tool in the field of chemistry. Its unique structure and biological activities make it an interesting subject for studying the relationship between chemical structure and biological function. Researchers can use 6H-Benzofuro[3,2-c][1]benzopyran-6-one to explore new synthetic routes, investigate its interactions with various biological targets, and develop a better understanding of its potential applications in drug discovery and development.

InChI:InChI=1/C15H8O3/c16-15-13-9-5-1-3-7-11(9)17-14(13)10-6-2-4-8-12(10)18-15/h1-8H

Upstream product

• 34073-50-2 3-diazo-2,3-dihydro-2-benzofuranone 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 583-55-1 1-Bromo-2-iodobenzene 
• 615-42-9 1,2-Diiodobenzene 
• 615-41-8 2-iodochlorobenzene 
• 938-40-9 4-Bromo-2H-1-benzopyran-2-one 
• 35817-28-8 4-phenoxy-2H-1-benzopyran-2-one 
• 68903-74-2 3-iodo-4-phenoxy-2H-chromen-2-one 
• 108-95-2 phenol 
• 767-91-9 1-ethynyl-2-methoxybenzene 
• 93316-18-8 2,3-bis-(2-methoxy-phenyl)-3-oxo-propionitrile 

Relevant articles and documents

One-pot two-step synthesis of 3-iodo-4-aryloxy coumarins and their Pd/C-catalyzed annulation to coumestans

An efficient protocol for the synthesis of various coumestans from the intramolecular annulation of 3-iodo-4-aryloxy coumarins through C-H activation has been developed. When 3-iodo-4-aryloxy coumarins were treated with 10% Pd/C (0.3 mol% Pd) in the presence of sodium acetate, the corresponding coumestans were produced in good to excellent yield. Reusability of the palladium catalyst was investigated in up to three consecutive cycles and it was found that the yield of the reaction was almost unaltered. Sequential iodination and O-arylation of 4-hydroxy coumarins leading to the 3-iodo-4-aryloxy coumarins were also achieved in a one-pot two-step process starting from aryl iodides in high yield. Pivalic acid was revealed to be the most effective additive for the later method to produce 3-iodo-4-phenoxy coumarins. Different functional groups bearing electron-donating as well as withdrawing groups are also tolerant to the reaction conditions.

Mechanistic studies on the palladium-catalyzed cross-dehydrogenative coupling of 4-phenoxy-2-coumarins: Experimental and computational insights

Delineating the mechanistic features of C-H activation in aryl-heteroaryl coupling is an important step in the design of selective, catalytic processes. Herein we use the intramolecular dehydrogenative coupling of 4-phenoxy-2-coumarins as a model study. Computational results and experimental studies suggest that CMD is operative in the cleavage of both C-H bonds, and that the heteroaryl C-H is cleaved initially.

Cyclization of 4-Phenoxy-2-coumarins and 2-Pyrones via a Double C-H Activation

Aryl-heteroaryl coupling via double C-H activation is a powerful transformation that avoids the installation of activating groups. A double C-H activation of privileged biological scaffolds, 2-coumarins and 2-pyrones, is reported. Despite the rich chemistry of these molecular frameworks, the yields are very good. Excellent regioselectivity was achieved on the pyrones. This methodology was applied to the synthesis of flemichapparin C in three steps. Isotope effect experiments were carried out, and a mechanism is proposed.

A different route to 3-aryl-4-hydroxycoumarins

We herein report the simple and direct arylation of 4-hydroxycoumarins by photoinduced reaction with aryl halides (iodobenzene, iodonaphthalene, 4-iodoanisole, 2-iodoanisole). Good yields of 3,4-disubstituted coumarins were obtained in these reactions (>60%). Extension of the procedure to the reaction with o-dihalobenzenes leads to the synthesis of ring closure products which bear a tetracyclic aromatic-condensed ring system, although in lower overall yields (≈45%).

An efficient synthesis of coumestrol and coumestans by iodocyclization and Pd-catalyzed intramolecular lactonization

The iodocyclization of acetoxy-containing 2-(1-alkynyl)anisoles and subsequent direct palladium-catalyzed carbonylation/lactonization provide an efficient route to naturally occurring coumestan and coumestrol, and their related analogues.

Photoreactions of 3-Diazo-3H-benzofuran-2-one; Dimerization and Hydrolysis of Its Primary Photoproduct, A Quinonoid Cumulenone: A Study by Time-Resolved Optical and Infrared Spectroscopy

Light-induced deazotization of 3-diazo-3H-benzofuran-2-one (1) in solution is accompanied by facile (CO)-O bond cleavage yielding 6-(oxoethenylidene)-2,4-cyclohexadien-1-one (3), which appears with a rise time of 28 ps. The expected Wolff-rearrangement product, 7-oxabicyclo[4.2.0]octa-1,3,5-trien-8-ylidenemethanone (4), is not formed. The efficient light-induced formation of the quinonoid cumulenone 3 opens the way to determine the reactivity of a cumulenone in solution. The reaction kinetics of 3 were monitored by nanosecond flash photolysis with optical (λ max ≈ 460 nm) as well as Raman (1526 cm-1) and IR detection (2050 cm-1). Remarkably, the reactivity of 3 is that expected from its valence isomer, the cyclic carbene 3H-benzofuran-2-one-3-ylidene, 2. In aqueous solution, acid-catalyzed addition of water forms the lactone 3-hydroxy-3H-benzofuran-2-one (5). The reaction is initiated by protonation of the cumulenone on its β-carbon atom. In hexane, cumulenone 3 dimerizes to isoxindigo ((E)-[3,3′ ]bibenzofuranylidene-2,2′-dione, 7), coumestan (6H-benzofuro[3,2-c][1]benzopyran-6-one, 8), and a small amount of dibenzonaphthyrone ([1]benzopyrano[4,3-][1]benzopyran-5,11-dione, 9) at a nearly diffusion-controlled rate. Ab initio calculations (G3) are consistent with the observed data. Carbene 2 is predicted to have a singlet ground state, which undergoes very facile, strongly exothermic (irreversible) ring opening to the cumulenone 3. The calculated barrier to formation of 4 (Wolff-rearrangement) is prohibitive. DFT calculations indicate that protonation of 3 on the β-carbon is accompanied by cyclization to the protonated carbene 2H +, and that dimerization of 3 to 7 and 9 takes place in a single step with negligible activation energy.