20050-72-0

Upstream product

• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 25307-01-1 p-tolylacetic acid sodium salt 
• 531-59-9 7-methoxycoumarin 
• 98-59-9 p-toluenesulfonyl chloride 
• 108-88-3 toluene 
• 766-97-2 4-n-methylphenylacetylene 
• 20050-74-2 7-hydroxy-3-(p-tolyl)-2H-chromen-2-one 
• 74-88-4 methyl iodide 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 622-47-9 4-tolylacetic acid 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 949580-73-8 3-(4-bromomethylphenyl)-7-methoxychromen-2-one 
• 878019-85-3 7-methoxy-3-(4-formylphenyl)coumarin 

Relevant academic research and scientific papers

Rational design of slightly twisted coumarin molecules with remarkable solution and solid dual efficient luminescence

Endowing slightly twisted molecules highly emissive in both solution and solid state is of great importance for understanding the principle of maximizing the luminescent efficiency of luminophores. To this end, a series of slightly twisted coumarin luminophores CMs with different alkoxyl substituents at the 7-positions were synthesized. The effect of the substitutes on the diversity photophysical properties of the four compounds in solution, THF/H2O mixtures and solid state were investigated. Comparing to the referenced compound CM (3-p-tolyl-2H-chromen-2-one) that without a substitute, the introduced electron-rich alkoxyl substitutes not only enhanced the intramolecular charge transfer (ICT) effect, but also significantly modified their molecular packing patterns in the crystals. The combined effect of increasing the radiative and suppressing the nonradiactive pathways boosted the luminescence efficiency of CM1-CM3 in solution and the solid state simultaneously. Eventually, compound CM2 with an ethoxyl substitute exhibited the strongest blue emission with fluorescence quantum yields as high as 73.2% and 96.7% in solution and the solid state, respectively. This work presents an efficient strategy towards dual strong fluorescent luminophores in both solution and the solid state.

Regioselective α-arylation of coumarins and 2-pyridones with phenylhydrazines under transition-metal-free conditions

A facile regioselective metal-free direct α-arylation of coumarins and 2-pyridones is achieved by the reaction of coumarins and 2-pyridones with phenylhydrazine in good yields. The reaction proceeds at room temperature under mild conditions using inexpensive reagents and without the need for step intensive activating groups. The methodology is operationally simple, practically viable and also allows the coupling of similar nitrogen heterocycle aza-coumarins without prerequisite N-protection.

A complete switch of the directional selectivity in the annulation of 2-hydroxybenzaldehydes with alkynes

Controlling reaction selectivity is an eternal pursuit for chemists working in chemical synthesis. As part of this endeavor, our group has been exploring the possibility of constructing different natural product skeletons from the same simple starting mat

Palladium catalyzed dehydrogenative arylation of coumarins: An unexpected switch in regioselectivity

A new regioselective α-arylation of coumarins with unactivated simple arenes via a palladium-catalyzed twofold C-H functionalization is devised. This method offers an attractive new approach to synthesis of a wide variety of 3-arylcoumarins from readily accessible starting materials. This journal is The Royal Society of Chemistry 2013.

Highly regioselective α-arylation of coumarins via palladium-catalyzed C-H activation/desulfitative coupling

A novel regioselective α-arylation of coumarins with readily available arenesulfonyl chlorides and sodium arenesulfinates via palladium-catalyzed direct C-H functionalizations under mild reaction conditions is described. This protocol presents an unexpected and highly regio-controlled arylation of coumarins at C-3 to construct interesting 3-arylcoumarins with fascinating biological and fluorescent properties. The regioselectivity observed is in sharp contrast with that expected for the Heck reactions. Copyright

Through-bond energy transfer cassettes with minimal spectral overlap between the donor emission and acceptor absorption: Coumarin-rhodamine dyads with large pseudo-stokes shifts and emission shifts

Chemical Equation Presented Cassette recording: A new class of coumarin-rhodamine through-bond energy-transfer (TBET) cassettes with minimal spectral overlap between the donor emission and the acceptor absorption (see picture) show large pseudo-Stokes shifts (up to 230 nm) and emission shifts (up to 170 nm). The utility of this TBET platform for TBET-based probe development was demonstrated by a new ratiometric fluorescence pH probe.

Extensive SAR and computational studies of 3-{4-[(benzylmethylamino)methyl] phenyl}-6,7-dimethoxy-2H-2-chromenone (AP2238) derivatives

AP2238 was the first compound published to bind both anionic sites of the human acetylcholinesterase, allowing the simultaneous inhibition of the catalytic and the amyloid-β pro-aggregating activities of AChE. Here we attempted to derive a comprehensive structure-activity relationship picture for this molecule, affording 28 derivatives for which AChE and BChE inhibitory activities were evaluated. Selected compounds were also tested for their ability to prevent the AChE-induced Aβ-aggregation. Moreover, docking simulations and molecular orbital calculations were performed.