22115-46-4

Usage

Chemical class

Benzopyranone derivatives

Molecular weight

283.24 g/mol

Core structure

Benzopyranone

Substituent

4-nitrophenyl group

Position of substituent

3

Usage

Building block in the synthesis of pharmaceutical compounds and other organic molecules

Biological activities

Exhibits various biological activities

Potential applications

Medicine and pharmaceutical research

Handling precautions

May pose health risks if not properly managed

Upstream product

• 89-51-0 Homophthalic acid 
• 99-77-4 ethyl 4-nitrobenzoate 
• 122-04-3 4-nitro-benzoyl chloride 
• 1382352-94-4 1-(2-iodophenyl)-3-(4-nitrophenyl)-1,3-propanedione 
• 51050-54-5 3-Chloroisocoumarin 
• 24067-17-2 4-nitrophenylboronic acid 
• 130818-21-2 2-(2-(4-nitrophenyl)ethynyl)benzoic acid methyl ester 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 88-67-5 2-Iodobenzoic acid 
• 214550-39-7 3-(4'-nitrophenyl)isochromane 

Relevant academic research and scientific papers

Synthesis of some 3-substituted isochromen-1-ones

An alternative method for the synthesis of 3-substituted isocoumarins from homophthalic acid and ester is described. Copyright Taylor & Francis Group, LLC.

Lactonization of 2-Alkynylbenzoates for the Assembly of Isochromenones Mediated by BF3·Et2O

A general and efficient lactonization method of readily available 2-alkynylbenzoates affording biologically important isochromenones has been realized via a solely BF3·Et2O-mediated 6-endo-dig cyclization process under mild condition

Silver triflate/: P -TSA co-catalysed synthesis of 3-substituted isocoumarins from 2-alkynylbenzoates

In this paper, we describe the silver triflate/p-toluenesulfonic acid co-catalysed synthesis of seventeen isocoumarins and two thieno[2,3-c]pyran-7-ones starting from 2-alkynylbenzoates and 3-alkynylthiophene-2-carboxylates, respectively. The reaction proceeds with absolute regioselectivity under mild reaction conditions and low catalyst loading, to afford the desired products in good to excellent yields. A conceivable reaction mechanism is proposed and supported by isotope-exchange tests, 1H NMR studies and ad hoc experiments.

A aqueous phase catalytic cascade reaction in the synthesis of isocoumarin derivatives of the method (by machine translation)

The invention provides a method for the aqueous phase catalytic cascade reaction in the synthesis of isocoumarin derivatives of the method, which is based on the concentration in the aqueous phase is 0.1 — 1 mol/L of ortho-halo benzoic acid 1 μM with 0.1 μM — 5 μM terminal alkyne in of 0.001 μM — 1 μM catalyst bivalent copper salt and O-phenanthrene under the catalytic action of, in 0.5 μM — 6 μM inorganic base or organic base in the presence of, in 20o C — 160 o C lower reaction 1h — 50h one pot synthesis isocoumarin derivatives. The invention is an environment-friendly, the operation is simple, cheap and safe, efficient to prepare the isocoumarin compound of the novel method, compared with the prior art, not only can be applied to a large number of functional groups, but also with simple operation, high yield, single product, convenient separation and purification, safe and cheap, small pollution and the like. (by machine translation)

Palladium catalyzed Suzuki Miyaura cross coupling of 3-chloroisochromen-1-one: Synthesis of glomellin and reticulol analogues

A facile protocol has been developed for a series of 3-substituted isochromen-1-ones utilizing Suzuki coupling strategy. The reaction of 3-chloroisochromen-1one, 1 with different boronic acids utilizing PdCl2(PPh3)2-Ruphos catalytic system gave diversified 3-substituted isochromen-1-ones in excellent yields. The methodology has been utilized in the synthesis of glomellin and reticulol analogues.

Synthesis of 3-substituted isocoumarins via a cascade intramolecular Ullmann-type coupling-rearrangement process

A simple and highly efficient strategy for the synthesis of 3-substituted isocoumarins through a copper(I)-catalyzed reaction of 1-(2-halophenyl)-1,3- diones has been developed. The procedure is based on a cascade copper-catalyzed intramolecular Ullmann-type C-arylation and rearrangement process. This methodology is tolerant of a wide range of substrates and applicable to library synthesis.

3-Substituted isocoumarins as thymidine phosphorylase inhibitors

3-Substituted isocoumarins 1-19 were synthesized and evaluated for their thymidine phosphorylase inhibitory activity. Eight (8) compounds exhibited a varying degree of inhibitory activity towards thymidine phosphorylase from E. coli with IC50 values between 61- 402 μM. The activities were compared with the standard 7-deazaxanthine (IC50 = 39.28 ± 0.76 μM).

Oxidation of 3-arylisochromans by dimethyldioxirane. An easy route to substituted 3-arylisocoumarins

The selective oxidation of the two different benzylethereal position of 3-arylisochromans by dimethyldioxirane as a function of different substituents on the aromatic rings was studied. The easy oxidation of these compounds was exploited for a new easy ac