61699-01-2

Basic information

• Product Name: 3H-Naphtho[2,1-b]pyran-2-carboxaldehyde
• CAS NO: 61699-01-2
• Molecular Formula: C14H10O2
• Molecular Weight: 210.232
• Mol File: 61699-01-2.mol

Chemical Properties

• Melting Point: 145-146 °C
• Boiling Point: 407.4±44.0 °C(Predicted)
• Density: 1.319±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 3H-Naphtho[2,1-b]pyran-2-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-Naphtho[2,1-b]pyran-2-carboxaldehyde(61699-01-2)
• EPA Substance Registry System: 3H-Naphtho[2,1-b]pyran-2-carboxaldehyde(61699-01-2)

Safety Data

• Hazardous Substances Data: 61699-01-2(Hazardous Substances Data)

Upstream product

• 107-02-8 acrolein 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 

Relevant articles and documents

Design, synthesis, and antidepressant/anticonvulsant activities of 3H-benzo[f]chromen chalcone derivatives

In this study, 19 3H-benzo[f]chromen chalcone derivatives (2a–2s) were obtained from 2-hydroxy-1-naphthaldehyde as the starting material, and their structures were confirmed by IR, 1H NMR, 13C NMR, and ESI-MS analyses. The antidepressant activities of the compounds were evaluated in mice after one 30 mg/kg dose by means of forced swimming tests, and 18 of the compounds (2a–2l, 2n–2s) showed antidepressant activity, of which three (2b, 2d, and 2n) showed strong antidepressant activity. Furthermore, all the compounds showed some anticonvulsant activity, with 11 of the compounds (2a–2g, 2k, 2m, 2n, and 2q) inhibiting convulsions in the maximal electroshock seizure (MES) test after one dose of 100 mg/kg, and the other eight inhibiting convulsions in the MES after one dose of 300 mg/kg. In the tail suspension test, all the compounds did not show neurotoxicity at the same dose. This research provides an experimental theoretical basis for finding new antidepressants with high biological activity and few side effects.

Reversible Ratiometric Fluorescent Probe for Sensing Bisulfate/H2O2 and Its Application in Zebrafish

Herein, a novel near-infrared fluorescent probe for ratiometric detection of bisulfate was designed and developed based on a conjugation of naphthopyran-benzothiazolium system. The sensor showed excellent selectivity, high sensitivity and a rapid response toward bisulfite in aqueous solution. Upon the addition of HSO3-, the sensor displayed 37-fold (I520/I630) fluorescence intensity enhancement, accompanied by an apparent color change from violet to colorless, suggesting that the sensor can be used to detect HSO3- with naked-eye . Notably, the addition product can be applied to the design of regenerative chemodosimeters based on the H2O2 promoted elimination of bisulfite and recovery of probe 1. Further cell and zebrafish imaging experiment demonstrated that the sensor could image the bisulfite/H2O2 redox cycle in biological system with ratiometric manners.

A new colorimetric and ratiometric fluorescent probe for selective recognition of cyanide in aqueous media

A simple naphthopyran derivative (L) has been synthesized as a colorimetric and ratiometric fluorescent probe for cyanide sensing in the aqueous DMSO medium and paper strips. The nucleophilic addition of CN? to this probe blocks the π-conjugation and the intramolecular charge transfer (ICT) transition between naphthopyran and benzoindolium moieties and consequently results in remarkable color and spectral changes. Upon addition of cyanide, L displayed a ratiometric fluorescence response with a blue shift of the peak position and a noticeable color change from fuchsia to colorless within 90 s. The probe exhibits high selectivity and sensitivity toward CN? over other anions and the detection limit was calculated to be 7.56 × 10?7 M, which is well below the WHO cyanide standard in drinking water (1.9 μM). In addition, the excitation and emission of the probe were within the visible wavelength range, which could benefit an application of the probe in an inexpensive portable cyanide sensor. The sensing ability of L has been successfully applied in real water samples. Furthermore, test strips based on L were fabricated, which can act as convenient and efficient test kits for detecting CN?.

Chalcone derivatives bearing chromen or benzo[f]chromen moieties: Design, synthesis, and evaluations of anti-inflammatory, analgesic, selective COX-2 inhibitory activities

Thirty-eight chalcone derivatives bearing a chromen or benzo[f]chromen moiety were synthesized and evaluated for their anti-inflammatory and analgesic activities. Using an ear edema model, anti-inflammatory activities were observed for compounds 3a-3s (ear inflammation: 1.75–3.71 mg) and 4a-4s (ear inflammation: 1.71–4.94 mg). All compounds also displayed analgesic effects with inhibition values of 66.7–100% (3a-3s) and 96.2–100% (4a-4s). The 12 compounds that displayed excellent anti-inflammatory and analgesic effects were tested for their inhibitory activity against ovine COX-1 and COX-2. Six compounds bearing a chromen moiety were weak inhibitors of the COX-1 isozyme but showed moderate COX-2 isozyme inhibitory effects (IC50s from 0.37 μM to 0.83 μM) and COX-2 selectivity indexes (SI: 22.49–9.34). Those bearing a benzo[f]chromen moiety were more selective toward COX-2 than those bearing a chromen moiety with IC50s from 0.25 μM to 0.43 μM and COX-2 selectivity indexes from SI: 31.08 to 20.67.

Design, one-pot synthesis, molecular docking study, and antibacterial evaluation of novel 2H-chromene based imidazo[1,2-a]pyridine derivatives as potent peptide deformylase inhibitors

An efficient, environmentally friendly, one-pot three-component synthesis of a series of 2H-chromene-based imidazo[1,2-a]pyridines had been designed and were synthesized. This protocol was developed by the reaction of substituted 2H-chromene aldehydes and

Naphthopyran aldehyde derivative as well as preparation method and application thereof

The invention belongs to the technical field of analytical chemistry, and relates to a naphthopyran aldehyde derivative as well as a preparation method and application thereof. The naphtho-pyranal derivative fluorescent probe prepared by the preparation method disclosed by the invention shows relatively high selective recognition performance on bisulfite in various common anions. When bisulfite isadded into a probe solution, green fluorescence is remarkably weakened, and naked eye discrimination and detection can be realized. In the using process of the probe, only a trace amount of DMSO (0.5%) is needed for hydrotropy, a fluorescence output signal is efficient and stable aggregation-induced emission, the concentration change of bisulfite in living cells can be monitored, and the probe has wide potential application value.

Reagent for detecting hydrosulfite and synthetic method and application thereof

The invention provides a reagent for detecting hydrosulfite and a synthetic method and an application thereof. The reagent is a hemicyanine dye derivative: (E)-2-(2-(3H-benzo[f]chromen-2-yl)vinyl)-2-methylbenzo[d]thiazol-3-ium idodie, and the Chinese name is (E)-2-(2-(3H-benzo[f]chromen-2-yl)vinyl)-2-methylbenzo[d]thiazol-3-ium idodie. The detection method comprises the step of quantifying the content of HSO3 through a fluorospectro photometer in a PBS-DMSO(9:1, v/v) buffer solution, the pH of which is 7.4. The detection process is simple, sensitive and fast, and the detection result is accurate.

Copper-catalyzed enantioselective henry reaction of enals and subsequent iodocyclization: Stereoselective construction of chiral azatricyclic frameworks

In the frame: A cascade sequence combining an asymmetric Henry reaction and a stereoselective intramolecular iodocyclization provides direct access to an enantioenriched tricyclic hexahydrochromeno[4,3-b]pyrrole framework (see scheme). The Henry reaction is catalyzed by copper in the presence of L1. Copyright

Thieme Chemistry Journal Awardees - Where are they now? Microwave-assisted rhodium-catalyzed decarbonylation of functionalized 3-formyl-2H-chromenes: A sequence for functionalized chromenes like deoxycordiachromene

3-Formyl-2H-chromenes which are readily accessible through an oxa-Michael reaction of salicylaldehydes and α,β-unsaturated aldehydes undergo a smooth decarbonylation reaction upon treatment with rhodium catalysts. With our method, a great variety of funct

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.