33177-29-6

Usage

Uses

Used in Pharmaceutical Industry:
5,6-Dihydro-4-hydroxy-6-methyl-2H-pyran-2-one is used as a synthetic intermediate for the preparation of spiro-γ/δ-dilactone, which is a mixture of diastereomers. These compounds have potential applications in the development of new pharmaceuticals due to their unique structural features and potential biological activities.
Used in Chemical Synthesis:
In the field of chemical synthesis, 5,6-Dihydro-4-hydroxy-6-methyl-2H-pyran-2-one is used as a building block for the synthesis of spiroheterocycles with fused heterosystems. These complex structures can be further modified and functionalized to create a wide range of compounds with diverse applications, including potential uses in materials science, pharmaceuticals, and agrochemicals.
Used in Agrochemical Industry:
5,6-Dihydro-4-hydroxy-6-methyl-2H-pyran-2-one is also utilized in the preparation of insecticidal heterolignans. These compounds are of interest in the development of new insecticides, as they may offer novel modes of action and selectivity against target pests, potentially reducing the reliance on traditional chemical insecticides.
Used in Organic Chemistry Research:
In the realm of organic chemistry research, 5,6-Dihydro-4-hydroxy-6-methyl-2H-pyran-2-one is employed in the cyclization of aminoanilino lactones on diazotization. This reaction provides a route to novel cyclic compounds with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

Synthesis Reference(s)

Chemistry Letters, 4, p. 161, 1975Journal of Heterocyclic Chemistry, 15, p. 1153, 1978 DOI: 10.1002/jhet.5570150717

InChI:InChI=1/C6H8O3/c1-4-2-5(7)3-6(8)9-4/h3-4,7H,2H2,1H3

Upstream product

• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 79039-99-9 5,6-dihydro-6-methyl-4-(N-phenylamino)-2-pyrone 

Downstream Products

• 79040-06-5 methyl-6 dihydro-5,6 N-parahydroxyphenylamino-4 pyrone-2 
• 133074-68-7 bis (5,6-dihydro-4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl) p-chlorophenylmethane 
• 79040-09-8 methyl-6 dihydro-5,6 N-metamethoxyphenylamino-4 pyrone-2 
• 133074-70-1 bis (5,6-dihydro-4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl) p-nitrophenylmethane 
• 133074-67-6 bis(5,6-dihydro-4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl) phenylmethane 
• 133074-69-8 bis (5,6-dihydro-4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl) p-methoxyphenylmethane 
• 79040-01-0 methyl-6 dihydro-5,6 N-paranitrophenylamino-4 pyrone-2 
• 18781-80-1 dihydrodehydroacetic acid 
• 79039-99-9 5,6-dihydro-6-methyl-4-(N-phenylamino)-2-pyrone 
• 79040-05-4 methyl-6 dihydro-5,6 N-metachlorophenylamino-4 pyrone-2 
• 79062-23-0 methyl-6 dihydro-5,6 N-orthoaminophenylamino-4-pyrone-2 
• 79040-00-9 methyl-6 dihydro-5,6 N-metatolylamino-4 pyrone-2 
• 3791-79-5 4-Methoxy-6-methyl-5,6-dihydro-2-pyranone 
• 79040-07-6 methyl-6 dihydro-5,6 N-metahydroxyphenylamino-4 pyrone-2 

Relevant academic research and scientific papers

PRODUCTION OF 2,4-HEXADIENOIC ACID AND 1,3-PENTADIENE FROM 6-METHYL-5,6-DIHYDRO-2-PYRONE

Described is a method of making sorbic acid, pentadiene, or 3-penten-2-one. The method includes partially hydrogenating 4-hydroxy-6-methyl-2-pyrone (HMP) to yield 5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one (4-DHMMP). Then, if 3-penten-2-one is desired, thermally decomposing the 4-DHMMP to yield 3-penten-2-one. If sorbic acid or pentadiene are desired, the 4-DHMMP is hydrogenated to yield 4-hydroxy-6-methyltetrahydro-2-pyrone (4-HMTHP). The 4-HMTHP is then dehydrated by contacting it with a solid acid catalyst to yield parasorbic acid (PSA). The PSA can then be ring-opened by contacting it with a solid acid catalyst. The reaction conditions of the ring-opening reaction can be controlled to yield sorbic acid and/or pentadiene.

Mechanism of hydrolysis and structure-stability relationship of enaminones as potential prodrugs of model primary amines

The objective of this work was to investigate the chemistry and the structure-stability relationship of enaminones (a class of enamines formed between a primary amine and a 1,3-dicarbonyl compound) and to evaluate their potential usefulness as prodrugs of primary amines. The acid-catalyzed degradation of the enaminones was found to be very sensitive to minor differences in the structure of the 1,3-dicarbonyl compound used to form the enaminone, but relatively insensitive to changes in the amine portion of the enaminones. A correlation was found between the rate of enaminone hydrolysis and the pK(a) of the 1,3-dicarbonyl compound, suggesting that the rate-controlling step in the hydrolysis of the enaminones was the proton addition to the vinyl carbon of the enaminone. Enaminones formed with cyclic 1,3-dicarbonyl compounds were significantly more stable than those formed with structurally similar acyclic compounds. Based on chemical stability considerations alone, enaminones do not appear to be good candidates as prodrugs of primary amines. Evidence is presented, however, that enaminones formed between amines and 1,3-ketoesters or lactones may be subject to enzyme-catalyzed degradation. Further research on the design of enaminones destabilized by a triggering enzymatic event that results in the loss of conjugation (e.g., ester or lactone hydrolysis or an oxidation/reduction event) may prove worth pursuing.

Enaminones as potential prodrugs of primary and secondary amines

Novel enzymatically labile enaminones useful as potential prodrugs of primary and secondary amines are disclosed. Also, disclosed herein are compositions comprising said amines and methods of administering said composition to warm-blooded animals.