Pyran compounds

Pyrans refer to hexaheterocyclic compounds containing one oxygen atom, including two isomers- α-pyran and γ-pyran. Pyran without substituents has not been found, but pyran derivatives are widely found in nature. α-pyrone and γ-pyrone mainly exist in plants. Benzopyran (chromene), chromone, coumarin, flavonoid, isoflavone and anthocyanin can be regarded as pyran derivatives.

The electronic structure of pyran is similar to that of benzene. The oxygen atom in the hexaheterocyclic ring has a strong alkalinity. Pyran is stabilized after its salification. Many important natural substances such as pigments, sugars, antibiotics and alkaloids, contain the ring system of pyran or pyrylium salts. E.g. six-member ring hemiacetal structures in the form of pentose or hexose are called pyranose.

Pyrone can be considered as the product of oxidation methine part of pyran into carbonyl group. A-pyrone, as the lactone of 5-hydroxy-2,4-pentadienoic acid, can participate in the hydrolysis reaction under acid-base catalysis, also can be catalytically hydrogenated into 5-hydroxyvalerate lactone, although its carbonyl is not easy to reduced. A-pyrone can also participate in diene synthesis. Γ-pyrone is different, it has a significant aromaticity. Although it is an unsaturated ketone, it cannot form hydrazone with phenylhydrazine. Also its carbonyl is not prone to reduction reaction. Some important medicines such as erythromycin and dihydrostreptomycin contain a tetrahydropyran ring. Many carbohydrates contain tetrahydropyran ring structures.

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Structure Chemical Name CAS MF
2-HYDROXYTETRAHYDROPYRAN 2-HYDROXYTETRAHYDROPYRAN 694-54-2 C5H10O2
7-HYDROXYCOUMARIN-3-CARBOXYLIC ACID 7-HYDROXYCOUMARIN-3-CARBOXYLIC ACID 779-27-1 C10H6O5
Tetrahydro-4H-Pyran-4-one Tetrahydro-4H-Pyran-4-one 143562-54-3
6,7,8-TRIMETHOXYCOUMARIN 6,7,8-TRIMETHOXYCOUMARIN 6035-49-0 C12H12O5
N-(TETRAHYDRO-2H-PYRAN-2-YLOXY)SUCCINIMIDE N-(TETRAHYDRO-2H-PYRAN-2-YLOXY)SUCCINIMIDE 55610-40-7 C9H13NO4
METHYL TETRAHYDRO-4-OXO-2H-THIOPYRAN-3-CARBOXYLATE METHYL TETRAHYDRO-4-OXO-2H-THIOPYRAN-3-CARBOXYLATE 4160-61-6 C7H10O3S
TETRAHYDRO-2H-PYRAN-4-CARBOXAMIDE TETRAHYDRO-2H-PYRAN-4-CARBOXAMIDE 344329-76-6 C6H11NO2
2-(TETRAHYDRO-PYRAN-4-YL)-ETHANOL 2-(TETRAHYDRO-PYRAN-4-YL)-ETHANOL 4677-18-3 C7H14O2
5,6-DIHYDRO-4-HYDROXY-6-METHYL-2H-PYRAN-2-ONE 5,6-DIHYDRO-4-HYDROXY-6-METHYL-2H-PYRAN-2-ONE 33177-29-6 C6H8O3
3,4-DIHYDRO-6-[(TERT-BUTYL)DIMETHYL SILYLOXY]-2H-PYRAN 3,4-DIHYDRO-6-[(TERT-BUTYL)DIMETHYL SILYLOXY]-2H-PYRAN 130650-09-8 C11H22O2Si
4-CHLORO-3-NITROCOUMARIN 4-CHLORO-3-NITROCOUMARIN 38464-20-9 C9H4ClNO4
6-BROMOFLAVONE 6-BROMOFLAVONE 1218-80-0 C15H9BrO2
4-BROMOMETHYL-6,7-DIMETHOXYCOUMARIN 4-BROMOMETHYL-6,7-DIMETHOXYCOUMARIN 88404-25-5 C12H11BrO4
Ethyl Tetrahydropyran-4-Carboxylate Ethyl Tetrahydropyran-4-Carboxylate 96835-17-5 C8H14O3
3-CHLOROCOUMARIN 3-CHLOROCOUMARIN 92-45-5 C9H5ClO2
3-CYANOCHROMONE 3-CYANOCHROMONE 50743-17-4 C10H5NO2
2-AMINO-3-FORMYLCHROMONE 2-AMINO-3-FORMYLCHROMONE 61424-76-8 C10H7NO3
7-AMINO-4-(METHOXYMETHYL)COUMARIN 7-AMINO-4-(METHOXYMETHYL)COUMARIN 175205-10-4 C11H11NO3
2-(BROMOMETHYL)TETRAHYDRO-2 H-PYRAN 2-(BROMOMETHYL)TETRAHYDRO-2 H-PYRAN 34723-82-5 C6H11BrO
6-BROMO-3-BUTYRYL-2H-CHROMEN-2-ONE 6-BROMO-3-BUTYRYL-2H-CHROMEN-2-ONE 2199-83-9 C13H11BrO3
3-CARBETHOXYUMBELIFERONE 3-CARBETHOXYUMBELIFERONE 6093-71-6 C12H10O5
3-Cyano-7-hydroxycoumarin 3-Cyano-7-hydroxycoumarin 19088-73-4 C10H5NO3
2-(6-CHLOROHEXYLOXY)TETRAHYDRO-2H-PYRAN& 2-(6-CHLOROHEXYLOXY)TETRAHYDRO-2H-PYRAN& 2009-84-9 C11H21ClO2
TETRAHYDRO-2H-PYRAN-4-YLACETYL CHLORIDE TETRAHYDRO-2H-PYRAN-4-YLACETYL CHLORIDE 40500-05-8 C7H11ClO2
4-AMINO-4-CARBOXYTETRAHYDROTHIOPYRAN HYDROCHLORIDE 4-AMINO-4-CARBOXYTETRAHYDROTHIOPYRAN HYDROCHLORIDE 67639-41-2 C6H12ClNO2S
7-DIETHYLAMINO-3-THENOYLCOUMARIN 7-DIETHYLAMINO-3-THENOYLCOUMARIN 77820-11-2 C18H17NO3S
2-(2-BROMOETHOXY)TETRAHYDRO-2H-PYRAN 2-(2-BROMOETHOXY)TETRAHYDRO-2H-PYRAN 172797-67-0 C7H13BrO2
6-ETHYL-3-FORMYLCHROMONE 6-ETHYL-3-FORMYLCHROMONE 42059-78-9 C12H10O3
3-CYANO-7-ETHOXYCOUMARIN 3-CYANO-7-ETHOXYCOUMARIN 117620-77-6 C12H9NO3
3-PHENYLUMBELLIFERONE 3-PHENYLUMBELLIFERONE 6468-96-8 C15H10O3
5,6-DIHYDRO-4-METHOXY-2H-PYRAN 5,6-DIHYDRO-4-METHOXY-2H-PYRAN 17327-22-9 C6H10O2
Coumarin 314T Coumarin 314T 113869-06-0 C22H27NO4
3-ACETAMIDOCOUMARIN 3-ACETAMIDOCOUMARIN 779-30-6 C11H9NO3
6-BROMO-3-CYANO-4-METHYLCOUMARIN 6-BROMO-3-CYANO-4-METHYLCOUMARIN 56394-22-0 C11H6BrNO2
1',3',3'-TRIMETHYL-6-HYDROXYSPIRO(2H-1-BENZOPYRAN-2,2'-INDOLINE) 1',3',3'-TRIMETHYL-6-HYDROXYSPIRO(2H-1-BENZOPYRAN-2,2'-INDOLINE) 23001-29-8 C19H19NO2
4-Cyanotetrahydropyran 4-Cyanotetrahydropyran 1836-77-7 C12H6Cl3NO3
6,8-DICHLORO-3-CYANOCHROMONE 6,8-DICHLORO-3-CYANOCHROMONE 72798-32-4 C10H3Cl2NO2
2-(2-OXO-2H-CHROMEN-7-YLOXY)-PROPIONIC ACID 2-(2-OXO-2H-CHROMEN-7-YLOXY)-PROPIONIC ACID 304889-93-8 C12H10O5
2-(6-BROMOHEXYLOXY)TETRAHYDRO-2H-PYRAN 2-(6-BROMOHEXYLOXY)TETRAHYDRO-2H-PYRAN 53963-10-3 C11H21BrO2
6-CHLORO-3-CYANOCHROMONE 6-CHLORO-3-CYANOCHROMONE 50743-20-9 C10H4ClNO2
2-OCTYLOXYTETRAHYDRO-2H-PYRAN 2-OCTYLOXYTETRAHYDRO-2H-PYRAN 70690-19-6 C13H26O2
1',3',3'-TRIMETHYLSPIRO-8-NITRO(2H-1-BENZOPYRAN)-2',2'-INDOLINE 1',3',3'-TRIMETHYLSPIRO-8-NITRO(2H-1-BENZOPYRAN)-2',2'-INDOLINE 5150-50-5 C19H18N2O3
2-N-Boc-Amino-3-(4-tetrahydropyranyl)propionic acid 2-N-Boc-Amino-3-(4-tetrahydropyranyl)propionic acid 182287-51-0 C13H23NO5
8-ACETYL-7-HYDROXYCOUMARIN 8-ACETYL-7-HYDROXYCOUMARIN 6748-68-1 C11H8O4
4-CHLORO-2-OXO-2H-CHROMENE-3-CARBALDEHYDE 4-CHLORO-2-OXO-2H-CHROMENE-3-CARBALDEHYDE 50329-91-4 C10H5ClO3
6-BROMO-3-CYANOCHROMONE 6-BROMO-3-CYANOCHROMONE 52817-13-7 C10H4BrNO2
3-ACETYL-7-HYDROXY-2H-CHROMEN-2-ONE 3-ACETYL-7-HYDROXY-2H-CHROMEN-2-ONE 10441-27-7 C11H8O4
7,8-DIHYDROXY-4-METHYLCOUMARIN 7,8-DIHYDROXY-4-METHYLCOUMARIN 2107-77-9 C10H8O4
3-acetyl-6-bromo-2H-chromen-2-one 3-acetyl-6-bromo-2H-chromen-2-one 2199-93-1 C11H7BrO3
2-(2-tert-Butyl-6-methylpyran-4-ylidene)malononitrile 2-(2-tert-Butyl-6-methylpyran-4-ylidene)malononitrile 225378-53-0 C13H14N2O
4-Chloromethyl-6-methyl-chromen-2-one ,97% 4-Chloromethyl-6-methyl-chromen-2-one ,97% 41295-65-2 C11H9ClO2
2H-PYRAN-4-CARBOXYLIC ACID TETRAHYDRO ETHYL ESTER 2H-PYRAN-4-CARBOXYLIC ACID TETRAHYDRO ETHYL ESTER C8H10O3
7-(CARBOXYMETHOXY)-4-METHYLCOUMARIN 7-(CARBOXYMETHOXY)-4-METHYLCOUMARIN 64700-15-8 C12H10O5
Coumarin 30 Coumarin 30 41044-12-6 C21H21N3O2
[(2-OXO-2H-CHROMEN-7-YL)OXY]ACETIC ACID [(2-OXO-2H-CHROMEN-7-YL)OXY]ACETIC ACID 126424-85-9 C11H8O5
6-HYDROXY-7-METHOXY-4-PHENYLCOUMARIN 6-HYDROXY-7-METHOXY-4-PHENYLCOUMARIN 482-83-7 C16H12O4
ETHYL 7-HYDROXY-4-OXO-4H-CHROMENE-2-CARBOXYLATE ETHYL 7-HYDROXY-4-OXO-4H-CHROMENE-2-CARBOXYLATE 23866-72-0 C12H10O5
7-HYDROXY-4-METHYL-3-COUMARINYLACETIC ACID 7-HYDROXY-4-METHYL-3-COUMARINYLACETIC ACID 5852-10-8 C12H10O5
7-Propoxy-chromen-2-one ,97% 7-Propoxy-chromen-2-one ,97% 6093-73-8 C12H12O3
8-HYDROXY-7-METHOXYCOUMARIN 8-HYDROXY-7-METHOXYCOUMARIN 19492-03-6 C10H8O4
4-Butylamino-chromen-2-one ,97% 4-Butylamino-chromen-2-one ,97% 21315-46-8 C13H15NO2
2-AMINO-6-CHLORO-3-FORMYLCHROMONE 2-AMINO-6-CHLORO-3-FORMYLCHROMONE 68301-77-9 C10H6ClNO3
3-CYANO-6,7-DIMETHYLCHROMONE 3-CYANO-6,7-DIMETHYLCHROMONE 94978-86-6 C12H9NO2
6-TERT-BUTYL-4-METHYLCOUMARIN 6-TERT-BUTYL-4-METHYLCOUMARIN 17874-32-7 C14H16O2
3,4-DIMETHYLUMBELLIFERONE 3,4-DIMETHYLUMBELLIFERONE 2107-78-0 C11H10O3
7-HYDROXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID METHYL ESTER 7-HYDROXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID METHYL ESTER 86788-49-0 C11H8O5
8-ACETYL-7-METHOXYCOUMARIN 8-ACETYL-7-METHOXYCOUMARIN 89019-07-8 C12H10O4
4-METHYLUMBELLIFERYL HEPTANOATE 4-METHYLUMBELLIFERYL HEPTANOATE 18319-92-1 C17H20O4
6-CHLORO-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID 6-CHLORO-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID 883-92-1 C10H5ClO4
6-METHYLCHROMONE 6-METHYLCHROMONE 38445-23-7 C10H8O2
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