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
Tetrahydro-4-pyranol Tetrahydro-4-pyranol 2081-44-9 C5H10O2
4-Hydroxycoumarin 4-Hydroxycoumarin 1076-38-6 C9H6O3
METHYL-(TETRAHYDRO-PYRAN-4-YL)-AMINE HCL METHYL-(TETRAHYDRO-PYRAN-4-YL)-AMINE HCL 220641-87-2 C6H13NO
Tetrahydropyran Tetrahydropyran 142-68-7 C5H10O
4-(2-Tetrahydropyranyloxy)phenylboronic acid 4-(2-Tetrahydropyranyloxy)phenylboronic acid 182281-01-2 C11H15BO4
Methyl tetrahydropyran-4-carboxylate Methyl tetrahydropyran-4-carboxylate 110238-91-0 C7H12O3
6-Bromo-2,3-dihydro-4H-chromen-4-one 6-Bromo-2,3-dihydro-4H-chromen-4-one 49660-57-3 C9H7BrO2
Tetrahydro-4H-pyran-4-one Tetrahydro-4H-pyran-4-one 29943-42-8 C5H8O2
4-Aminotetrahydropyran 4-Aminotetrahydropyran 38041-19-9 C5H11NO
4-Chromanone 4-Chromanone 491-37-2 C9H8O2
Tetrahydro-2H-pyran-4-carboxylic acid Tetrahydro-2H-pyran-4-carboxylic acid 5337-03-1 C6H10O3
3,4-Dihydro-2H-pyran 3,4-Dihydro-2H-pyran 110-87-2 C5H8O
(TETRAHYDRO-2H-PYRAN-4-YL)METHANOL (TETRAHYDRO-2H-PYRAN-4-YL)METHANOL 14774-37-9 C6H12O2
6-CHLORO-9-(TETRAHYDRO-2-PYRANYL)-PURINE 6-CHLORO-9-(TETRAHYDRO-2-PYRANYL)-PURINE 7306-68-5 C10H11ClN4O
2,3,4,6-Tetra-O-benzyl-D-glucopyranose 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 4132-28-9 C34H36O6
Kojic acid Kojic acid 501-30-4 C6H6O4
Tetrahydrothiopyran-4-one Tetrahydrothiopyran-4-one 1072-72-6 C5H8OS
O-(Tetrahydro-2H-pyran-2-yl)hydroxylamine O-(Tetrahydro-2H-pyran-2-yl)hydroxylamine 6723-30-4 C5H11NO2
2H-PYRAN-3(4H)-ONE, DIHYDRO- 2H-PYRAN-3(4H)-ONE, DIHYDRO- 23462-75-1 C5H8O2
8-Amino-4-oxo-2-(tetrazol-5-yl)-4H-1-benzopyran 8-Amino-4-oxo-2-(tetrazol-5-yl)-4H-1-benzopyran 110683-22-2 C10H7N5O2
Tetrahydropyran-4-carbaldehyde Tetrahydropyran-4-carbaldehyde 50675-18-8 C6H10O2
7,8-Dihydroxycoumarin 7,8-Dihydroxycoumarin 486-35-1 C9H6O4
Tetrahydro-2H-pyran-4-carbonyl chloride Tetrahydro-2H-pyran-4-carbonyl chloride 40191-32-0 C6H9ClO2
4-BROMOMETHYLTETRAHYDROPYRAN 4-BROMOMETHYLTETRAHYDROPYRAN 125552-89-8 C6H11BrO
Coumarin 6 Coumarin 6 38215-36-0 C20H18N2O2S
2-(CHLOROMETHYL)TETRAHYDROPYRAN 2-(CHLOROMETHYL)TETRAHYDROPYRAN 18420-41-2 C6H11ClO
3,4-Dihydro-2H-pyran-2-methanol 3,4-Dihydro-2H-pyran-2-methanol 3749-36-8 C6H10O2
SCOPARONE SCOPARONE 120-08-1 C11H10O4
4-Aminotetrahydropyran hydrochloride 4-Aminotetrahydropyran hydrochloride 33024-60-1 C5H12ClNO
2-(2-BROMOETHOXY)TETRAHYDRO-2H-PYRAN 2-(2-BROMOETHOXY)TETRAHYDRO-2H-PYRAN 59146-56-4 C7H13BrO2
7-Methoxycoumarin-4-acetic acid 7-Methoxycoumarin-4-acetic acid 62935-72-2 C12H10O5
bk-DMBDB (hydrochloride) bk-DMBDB (hydrochloride) 17763-12-1 C13H18ClNO3
4-(DICYANOMETHYLENE)-2-METHYL-6-(4-DIMETHYLAMINOSTYRYL)-4H-PYRAN 4-(DICYANOMETHYLENE)-2-METHYL-6-(4-DIMETHYLAMINOSTYRYL)-4H-PYRAN 51325-91-8 C19H17N3O
2-(2-BROMOETHOXY)TETRAHYDRO-2H-PYRAN 2-(2-BROMOETHOXY)TETRAHYDRO-2H-PYRAN 17739-45-6 C7H13BrO2
Centchroman Centchroman 31477-60-8 C30H35NO3
TETRAHYDROPYRAN-2-METHANOL TETRAHYDROPYRAN-2-METHANOL 100-72-1 C6H12O2
ISOPIMPINELLIN ISOPIMPINELLIN 482-27-9 C13H10O5
4-Oxo-4H-1-benzopyran-2-carboxylic acid 4-Oxo-4H-1-benzopyran-2-carboxylic acid 4940-39-0 C10H6O4
4-Bromomethyl-7-methoxycoumarin 4-Bromomethyl-7-methoxycoumarin 35231-44-8 C11H9BrO3
4,6-DICHLORO-2H-BENZOPYRAN-3-CARBOXALDEHYDE 4,6-DICHLORO-2H-BENZOPYRAN-3-CARBOXALDEHYDE 175205-58-0 C10H6Cl2O2
2-(3-CHLOROPROPOXY)TETRAHYDRO-2H-PYRAN 2-(3-CHLOROPROPOXY)TETRAHYDRO-2H-PYRAN 42330-88-1 C8H15ClO2
2,2-DIMETHYLTETRAHYDROPYRAN-4-ONE 2,2-DIMETHYLTETRAHYDROPYRAN-4-ONE 1194-16-7 C7H12O2
ALPHA-PYRONE ALPHA-PYRONE 504-31-4 C5H4O2
Bergapten Bergapten 484-20-8 C12H8O4
2-(3-BROMOPHENOXY)TETRAHYDRO-2H-PYRAN 2-(3-BROMOPHENOXY)TETRAHYDRO-2H-PYRAN 57999-49-2 C11H13BrO2
4-Cyanotetrahydro-4H-pyran 4-Cyanotetrahydro-4H-pyran 4295-99-2 C6 H9 N O
3,4-DIHYDRO-2-METHOXY-2H-PYRAN 3,4-DIHYDRO-2-METHOXY-2H-PYRAN 4454-05-1 C6H10O2
2-(3-BUTYNYLOXY)TETRAHYDRO-2 H-PYRAN 2-(3-BUTYNYLOXY)TETRAHYDRO-2 H-PYRAN 40365-61-5 C9H14O2
4-Methoxy-6-methyl-2H-pyran-2-one 4-Methoxy-6-methyl-2H-pyran-2-one 672-89-9 C7H8O3
1,1-Dioxo-tetrahydro-thiopyran-4-one 1,1-Dioxo-tetrahydro-thiopyran-4-one 17396-35-9 C5H8O3S
4-Hydroxy-6-methyl-2-pyrone 4-Hydroxy-6-methyl-2-pyrone 675-10-5 C6H6O3
4-CHLOROTETRAHYDROPYRAN 4-CHLOROTETRAHYDROPYRAN 1768-64-5 C5H9ClO
4-CHLORO-6-FLUORO-2H-BENZOPYRAN-3-CARBOXALDEHYDE 4-CHLORO-6-FLUORO-2H-BENZOPYRAN-3-CARBOXALDEHYDE 105799-69-7 C10H6ClFO2
4-(Aminomethyl)tetrahydro-2H-pyran 4-(Aminomethyl)tetrahydro-2H-pyran 130290-79-8 C6H13NO
4-Aminotetrahydro-2H-pyran acetate 4-Aminotetrahydro-2H-pyran acetate 1005498-91-8 C7H15NO3
4-METHYLUMBELLIFERYL PHOSPHATE DISODIUM SALT 4-METHYLUMBELLIFERYL PHOSPHATE DISODIUM SALT 22919-26-2 C10H10NaO6P
4-BROMO-TETRAHYDROPYRAN 4-BROMO-TETRAHYDROPYRAN 25637-16-5 C5H9BrO
4H-PYRAN-4-ONE 4H-PYRAN-4-ONE 108-97-4 C5H4O2
2-(4-BROMOPHENOXY)TETRAHYDRO-2H-PYRAN 2-(4-BROMOPHENOXY)TETRAHYDRO-2H-PYRAN 36603-49-3 C11H13BrO2
2-Formyl-3,4-dihydro-2H-pyran 2-Formyl-3,4-dihydro-2H-pyran 100-73-2 C6H8O2
2-(4-PENTYNYLOXY)TETRAHYDRO-2H-PYRAN  9& 2-(4-PENTYNYLOXY)TETRAHYDRO-2H-PYRAN 9& 62992-46-5 C10H16O2
2-(3-Bromopropoxy)tetrahydro-2H-pyran 2-(3-Bromopropoxy)tetrahydro-2H-pyran 33821-94-2 C8H15BrO2
Coumarin-6-carboxylic acid Coumarin-6-carboxylic acid 7734-80-7 C10H6O4
7-HYDROXY-4-(TRIFLUOROMETHYL)COUMARIN 7-HYDROXY-4-(TRIFLUOROMETHYL)COUMARIN 575-03-1 C10H5F3O3
4-(2-AMINOETHYL)TETRAHYDROPYRAN 4-(2-AMINOETHYL)TETRAHYDROPYRAN 65412-03-5 C7H15NO
5,6-DIHYDRO-2H-PYRAN-2-ONE 5,6-DIHYDRO-2H-PYRAN-2-ONE 3393-45-1 C5H6O2
Tetrahydropyranyl-4-acetic acid Tetrahydropyranyl-4-acetic acid 85064-61-5 C7H12O3
TRIOXSALEN TRIOXSALEN 3902-71-4 C14H12O3
4-METHYLUMBELLIFERYL PHOSPHATE 4-METHYLUMBELLIFERYL PHOSPHATE 3368-04-5 C10H9O6P
6-HYDROXYFLAVANONE 6-HYDROXYFLAVANONE 4250-77-5 C15H12O3
5,7-Dihydroxy-4-methylcoumarin 5,7-Dihydroxy-4-methylcoumarin 2107-76-8 C10H8O4
TETRAHYDRO-2-(2-PROPYNYLOXY)-2H-PYRAN TETRAHYDRO-2-(2-PROPYNYLOXY)-2H-PYRAN 6089-04-9 C8H12O2
2-(TETRAHYDRO-2H-PYRAN-2-YLOXY)ETHANOL 2-(TETRAHYDRO-2H-PYRAN-2-YLOXY)ETHANOL 2162-31-4 C7H14O3
5,7-Dimethoxycoumarin 5,7-Dimethoxycoumarin 487-06-9 C11H10O4
3-CARBOMETHOXY-2-PYRONE 3-CARBOMETHOXY-2-PYRONE 25991-27-9 C7H6O4
6-BROMOCOUMARIN-3-CARBOXYLIC ACID 6-BROMOCOUMARIN-3-CARBOXYLIC ACID 2199-87-3 C10H5BrO4
3-BROMOCHROMONE 3-BROMOCHROMONE 49619-82-1 C9H5BrO2
2-(2-NITROETHOXY)TETRAHYDROPYRAN 2-(2-NITROETHOXY)TETRAHYDROPYRAN 75233-61-3 C7H13NO4
3,4-DIHYDRO-6-METHYL-2H-PYRAN-2-ONE 3,4-DIHYDRO-6-METHYL-2H-PYRAN-2-ONE 3740-59-8 C6H8O2
7-ACETOXY-4-BROMOMETHYLCOUMARIN 7-ACETOXY-4-BROMOMETHYLCOUMARIN 2747-04-8 C12H9BrO4
2,4,6-TRIPHENYLPYRYLIUM TETRAFLUOROBORATE 2,4,6-TRIPHENYLPYRYLIUM TETRAFLUOROBORATE 448-61-3 C23H17BF4O
2-(2-CHLOROETHOXY)TETRAHYDRO-2H-PYRAN 2-(2-CHLOROETHOXY)TETRAHYDRO-2H-PYRAN 5631-96-9 C7H13ClO2
6-BROMO-3-FORMYLCHROMONE 6-BROMO-3-FORMYLCHROMONE 52817-12-6 C10H5BrO3
7-ETHOXYCOUMARIN 7-ETHOXYCOUMARIN 31005-02-4 C11H10O3
(TETRAHYDRO-PYRAN-4-YL)-ACETONITRILE (TETRAHYDRO-PYRAN-4-YL)-ACETONITRILE 850429-50-4 C7H11NO
3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN 3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN 6174-86-3 C10H7ClO3
2-(ALLYLOXY)TETRAHYDROPYRAN 2-(ALLYLOXY)TETRAHYDROPYRAN 4203-49-0 C8H14O2
2-BENZYLOXYTETRAHYDROPYRAN 2-BENZYLOXYTETRAHYDROPYRAN 1927-62-4 C12H16O2
3-CHLOROCOUMARIN 3-CHLOROCOUMARIN 92-45-5 C9H5ClO2
Ethyl Tetrahydropyran-4-Carboxylate Ethyl Tetrahydropyran-4-Carboxylate 96835-17-5 C8H14O3
4-BROMOMETHYL-6,7-DIMETHOXYCOUMARIN 4-BROMOMETHYL-6,7-DIMETHOXYCOUMARIN 88404-25-5 C12H11BrO4
3-CYANOCHROMONE 3-CYANOCHROMONE 50743-17-4 C10H5NO2
CHROMONE-3-CARBOXALDEHYDE CHROMONE-3-CARBOXALDEHYDE 17422-74-1 C10H6O3
7,8-DIHYDROXY-6-METHOXYCOUMARIN 7,8-DIHYDROXY-6-METHOXYCOUMARIN 574-84-5 C10H8O5
3,4-DIHYDRO-2,2-DIMETHYL-4-OXO-2H-PYRAN-6-CARBOXYLIC ACID 3,4-DIHYDRO-2,2-DIMETHYL-4-OXO-2H-PYRAN-6-CARBOXYLIC ACID 80866-93-9 C8H10O4
6-BROMOCHROMONE 6-BROMOCHROMONE 51483-92-2 C9H5BrO2
7-Methoxy-4-methylcoumarin 7-Methoxy-4-methylcoumarin 2555-28-4 C11H10O3
XANTHOTOXOL XANTHOTOXOL 2009-24-7 C11H6O4
COUMARIN 152 COUMARIN 152 53518-14-2 C12H10F3NO2
2-(TETRAHYDROFURFURYLOXY)TETRAHYDROPYRAN 2-(TETRAHYDROFURFURYLOXY)TETRAHYDROPYRAN 710-14-5 C10H18O3
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