51593-70-5

Usage

InChI:InChI=1/C11H10O2/c1-8(12)10-6-9-4-2-3-5-11(9)13-7-10/h2-6H,7H2,1H3

Upstream product

• 57543-66-5 2H-chromene-3-carbonitrile 
• 75-16-1 methylmagnesium bromide 
• 89-95-2 2-methyl-benzyl alcohol 
• 118-93-4 o-hydroxyacetophenone 
• 78-94-4 methyl vinyl ketone 
• 224317-66-2 2-(but-2-yn-1-yloxy)benzaldehyde 
• 90-02-8 salicylaldehyde 

Downstream Products

• 77479-42-6 C₁₈H₁₈N₂O₃S 

Relevant academic research and scientific papers

Copper-Catalyzed Asymmetric 1,2-Addition of Grignard Reagents to 3-Acyl 2 H -chromenes

Enones in which the carbon-carbon double bond is part of the pharmacologically important 2 H -chromene (2 H -1-benzopyran) nucleus undergo asymmetric copper-catalyzed 1,2-addition of Grignard reagents. High yields and enantiomeric excesses up to 84% are o

Application of baylis-hillman methodology in a chemoselective synthesis of 3-acyl-2h-1-chromenes

The applications of Baylis-Hillman methodology in a chemoselective synthesis of 3-acyl-2H-1-chromenes were discussed. It was found that the reaction of 2-hydroxybenzaldehydes with alkyl vinyl ketones in the presence of 1,4-diazabicyclo[2.2.2]octane proceeded with regioselective cyclisation. The analysis showed that the yield of 2H-1-choromenes was up to 87%.

Catalytical promiscuity of α-amylase: Synthesis of 3-substituted 2H-chromene derivatives via biocatalytic domino oxa-Michael/aldol condensations

An facile and green one-pot route has been developed for the synthesis of chromenes using salicylaldehyde and α,β-unsaturated ketones. α-Amylase from Bacillus subtilis shows excellent catalytic activity and exerts good adaptability to different substrates in the reaction. This promiscuous enzyme-catalyzed domino reaction not only extends the application of α-amylase from B. subtilis for new chemical transformations, but also provided an alternative synthetic method for 2H-chromene derivatives.

3-Phenylalkyl-2H-chromenes and -chromans as novel rhinovirus infection inhibitors

Following our studies on structure-activity relationships of anti-rhinovirus chromene and chroman derivatives, we designed and synthesized new series of 3-phenylalkyl-2H-chromenes and -chromans bearing differently sized, aliphatic linker chains between the two cycles. The cytotoxicity and the antiviral activity of the new compounds on human rhinovirus (HRV) serotype 1B and 14 infection were evaluated in HeLa cell cultures. Most of the tested compounds interfered with HRV1B multiplication in the micromolar or submicromolar concentrations while HRV14 was less susceptible. 3-[3-(4-Chlorophenyl)propyl]chroman (9c) was selected for preliminary mechanism of action studies due to its potent activity against both serotypes (IC50 of 0.48?μM and 1.36?μM towards HRV1B and 14, respectively) coupled with high selectivity (SI?=?206.18 and 73.26, respectively). Results of time of addition/removal studies suggest that 9c, similarly to related derivatives, behaves as a capsid binder interfering with some early events of the HRV1B infectious cycle.

Barluenga's reagent with HBF4 as an efficient catalyst for alkyne-carbonyl metathesis of unactivated alkynes

Barluenga's reagent (IPy2BF4, Py = pyridine) treated with HBF4 efficiently catalyzes the inter- and intramolecular alkyne-carbonyl metathesis of unactivated alkynes with aldehydes or ketones, most of which proceed at room temperature. This work represents the first catalytic application of the Barluenga's reagent.

Iron-catalyzed synthesis of functionalized 2H-chromenes via intramolecular alkyne-carbonyl metathesis

An iron-catalyzed intramolecular alkyne-aldehyde metathesis strategy of the alkynyl ether of salicylaldehyde derivatives has been developed which works under mild reaction conditions to produce the functionalized 2H-chromene derivatives. This protocol is compatible toward a wide range of functional groups, such as methoxy, fluoro, chloro, bromo, and phenyl groups. This method provides an atom-economical and environmentally friendly approach for the synthesis of a series of substituted 2H-chromenes.

Alkynes as synthetic equivalents to stabilized wittig reagents: Intra- and intermolecular carbonyl olefinations catalyzed by Ag(I), BF3, and HBF4

(Chemical Equation Presented) The first use of cationic silver (AgSbF 4) as a catalyst for intra- and intermolecular alkyne - carbonyl coupling to form conjugated enones is described, and a comparison to corresponding Bronsted acid (HBF4/

A convenient general synthesis of 3-substituted 2H-chromene derivatives

Reactions of 2-hydroxybenzaldehydes and 2-hydroxy-1-naphthaldehydes with various activated alkenes under Baylis-Hillman conditions have been shown to proceed with regioselective cyclisation to afford the corresponding 3-substituted chromene derivatives. In some cases competitive dimerisation of the alkene component was observed, and direct dimerisation in the absence of the aldehyde has been explored.

A new approach to the synthesis of chromene derivatives

3-Acetyl-5,6-benzopyran and 3-benzoyl-5,6-benzopyran have been simply prepared by condensation of methylvinyl ketone and phenylvinyl ketone with salicylaldehyde in an aqueous DABCO medium at room temperature.

Efficient syntheses of new heteroarotinoids through functional pyridylzinc reagents and palladium-catalyzed cross-coupling reactions

A convergent synthesis of heteroarotinoids 4, 5a, and 5b, bearing chromene rings in association with pyridyl or ethynylpyridyl moieties, from 6-bromo-2-pyridylzinc chloride (11) is described. This new functional heteroarylzinc reagent, readily accessible