135746-22-4

Basic information

• Product Name: (Z)-2-benzylidene-4-methoxybenzofuran-3(2H)-one
• CAS NO: 135746-22-4
• Molecular Weight: 252.269
• Mol File: 135746-22-4.mol

Chemical Properties

• CAS DataBase Reference: (Z)-2-benzylidene-4-methoxybenzofuran-3(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-benzylidene-4-methoxybenzofuran-3(2H)-one(135746-22-4)
• EPA Substance Registry System: (Z)-2-benzylidene-4-methoxybenzofuran-3(2H)-one(135746-22-4)

Safety Data

• Hazardous Substances Data: 135746-22-4(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 67-56-1 methanol 
• 40524-67-2 2'-Hydroxy-6'-methoxychalcone 
• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 1466-76-8 2-6-dimethoxybenzoic acid 
• 536-74-3 phenylacetylene 
• 128216-91-1 1-(2-hydroxy-6-methoxyphenyl)-3-phenylprop-2-yn-1-one 
• 40524-67-2 (E)-1-(2-hydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 135746-09-7 2'-hydroxy-6'-methoxychalcone epoxide 

Relevant articles and documents

An efficient synthesis of aurone derivatives by the tributylphosphine-catalyzed regioselective cyclization of o-alkynoylphenols

An organocatalytic regioselective synthes is of aurones from o-alkynoylphenols was achieved. A catalytic amount of tributylphosphine select ively induced the 5-exo cyclization of o-alkynoylphenols under ambient conditions leading to aurone derivatives in high to excellent yields.

In vitro inhibitory properties of ferrocene-substituted chalcones and aurones on bacterial and human cell cultures

Two series of ten chalcones and ten aurones, where ferrocene replaces the C ring and with diverse substituents on the A ring were synthesized. The compounds were tested against two antibiotic-sensitive bacterial strains, E. coli ATCC 25922 and S. aureus ATCC 25923, and two antibiotic-resistant strains, S. aureus SA-1199B and S. epidermidis IPF896. The unsubstituted compound and those with methoxy substitution showed an inhibitory effect on all bacterial strains at minimum inhibitory concentrations ranging between 2 and 32 mg L -1. For four of these compounds, the effect was bactericidal, as opposed to bacteriostatic. The corresponding organic aurones did not show growth inhibition, underscoring the role of the ferrocene group. The methoxy-substituted aurones and the unsubstituted aurone also showed low micromolar (IC50) activity against MRC-5 non-tumoral lung cells and MDA-MB-231 breast cancer cells, suggesting non-specific toxicity.

Synthesis of Flavonols via Pyrrolidine Catalysis: Origins of the Selectivity for Flavonol versus Aurone

A novel synthetic method for flavonol from 2′-hydroxyl acetophenone and benzaldehyde promoted by pyrrolidine under an aerobic condition in water is established. This protocol was supported by efficient synthesis of 44 common examples and three natural products. The α, β-unsaturated iminium ion (enimine ion E) was proved to be the key intermediate in the reaction. H218O and 18O2 isotope tracking experiments demonstrated that both water and the aerobic atmosphere were necessary to ensure the transformation. The selectivity for flavonol or aurone was originated from solvent-triggered intermediates, which were determined by UV-visible spectra from isolated enimine. The phenol-iminium E-A is dominant in water and the ketoenamine intermediate E-B is prevalent in acetonitrile. In the presence of pyrrolidine and oxygen, E-A leads to flavonol through E-I, a zwitterionic-like phenoloxyl-iminium ion, following the key steps of cyclization and a [2 + 2] oxidation; E-B proceeds through path II, a radical process induced by photolysis of E-B with both pyrrolidine and oxygen, to afford aurone. Preliminary mechanistic studies are reported.

Metal-free methodology for the preparation of sterically hindered alkynoylphenols and its application to the synthesis of flavones and aurones

A metal-free synthesis for the preparation of sterically demanding ortho-demethylated ynones from mixed anhydrides and potassium alkynyltrifluoroborate salts has been developed. The one-pot reaction proceeds rapidly in the presence of a Lewis acid without the exclusion of air and moisture. This method is advantageous in that it is operationally simple, proceeds under mild conditions, and has a broad substrate scope. 2,6-Dimethoxy substituted anhydrides afford the corresponding mono-demethylated ynone products in good yields. In particular, 2-hydroxy substituted ynone products are valuable synthetic intermediates because their conversion to biologically active natural product scaffolds is straightforward. Flavones were obtained via 6-endo cyclization of the o-alkynyoylphenol intermediates under acidic conditions. Cesium carbonate was found to promote rapid 5-exo cyclization to furnish aurone products.

Oxidative rearrangement of 2′-hydroxychalcones having no substituent at the 3′- and 5′-positions with thallium(III) nitrate in methanol

Oxidation of 2′-hydroxychalcones with no substituents at the 3′- and 5′-positions with thallium(III) nitrate (TTN) in methanol has been studied in detail and the following results obtained. (1) 2′-Hydroxy-4,6′-dimethoxychalcones (1b and 2b) have increased

Kinetics and Mechanism of the Cyclisation of Some 2'-Hydroxychalcone Epoxides and Subsequent Elimination Reactions of Aurone Hydrates

Analysis of the pH-rate profile for the cyclisation of the monoanion of 2'-hydroxychalcone epoxide which gives 3-hydroxyflavanone and of some 6'-alkoxy-substituted analogues which give mostly aurone hydrate, gives rate coefficients which quantify the preference for α over β cyclisation when 6'-substituents are present.These are considered in terms of stereoelectronic factors which may be responsible for the preference.Also reported are rate coefficients for the subsequent reaction of aurone hydrates in which aurones and coumaranones are formed.

Cyclisation and subsequent reactions of 2′-hydroxy-6′-methoxychalcone epoxide and related compounds

2′-Hydroxy-6′-methoxychalcone epoxide reacts in neutral aqueous acetonitrile solution to give a 6:1 ratio of the α- and β-cyclisation products, erythro-4-methoxyaurone hydrate [erythro-2-(α-hydroxybenzyl)-4-methoxycoumaran-3-one] and trans-3-hydroxy-5-methoxyflavanone: the dominance of α-cyclisation may be associated with a stereoelectronic preference for a conformation favourable for α- but not β-cyclisation when the carbonyl group is forced by the 6′-substituent to lie out-of-plane with the aromatic ring. In more basic solutions, erythro-threo isomerisation of aurone hydrate occurs, and 4-methoxycoumaran-3-one and 4-methoxyaurone are formed. Other 6′-substituted 2′-hydroxychalcone epoxides show a similar strong preference for α- over β-cyclisation.