3,4-Dihydro-2H-pyran-2-one

Base Information

• Chemical Name: 3,4-Dihydro-2H-pyran-2-one
• CAS No.: 26638-97-1
• Molecular Formula: C5H6 O2
• Molecular Weight: 98.1014
• DSSTox Substance ID: DTXSID30181179
• Nikkaji Number: J1.535.379A
• Wikidata: Q83051788
• Mol file: 26638-97-1.mol

Synonyms:3,4-Dihydro-2H-pyran-2-one;2H-Pyran-2-one, 3,4-dihydro-;3,4-dihydropyran-2-one;26638-97-1;5-Hydroxy-4-pentenoic acid d-lactone;4,5-Dehydrovalerolactone;3,4-Dihydro-2H-pyron;DTXSID30181179;CHEBI:195197

Chemical Property of 3,4-Dihydro-2H-pyran-2-one

Chemical Property:

• Vapor Pressure: 0.398mmHg at 25°C
• Boiling Point: 196.4°C at 760 mmHg
• Flash Point: 69.6°C
• PSA: 26.30000
• Density: 1.123g/cm³
• LogP: 0.83710
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 98.036779430
• Heavy Atom Count: 7
• Complexity: 105

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)OC=C1

Technology Process of 3,4-Dihydro-2H-pyran-2-one

There total 5 articles about 3,4-Dihydro-2H-pyran-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4-pentynoic acid (6089-09-4) → 5,6-dihydro-2H-pyran-2-one (26638-97-1)

Guidance literature:

(hydridotris(pyrazolyl)borate)Ru(H)(triphenylphospine)2; In toluene; for 6h; Heating;

DOI:10.1039/b106647c

Reference yield: 64.0%

cyclopent-2-enone (930-30-3) → 5,6-dihydro-2H-pyran-2-one (26638-97-1)

Guidance literature:

With Baeyer–Villiger monooxygenase from Parvibaculum lavamentivorans DSM 13023; In ethanol; at 23 ℃; Enzymatic reaction;

DOI:10.1039/c4cc02541e

Reference yield:

4-pentynoic acid (6089-09-4) → 5-methylenedihydrofuran-2-one (10008-73-8) + 5,6-dihydro-2H-pyran-2-one (26638-97-1)

Guidance literature:

With [(1,3,4-triphenyl-4,5-dihydro-1H-triazol-5-ylidene)RuCl₂(CHPh)(tricyclohexylphosphine)]; In toluene; at 110 ℃; for 2.5h; regioselective reaction;

DOI:10.1016/S0022-328X(03)00074-3

upstream raw materials:

4-pentynoic acid

5-hydroxymethyl-4,5-dihydrofuranone

cyclopent-2-enone

Downstream raw materials:

5,6-dihydro-2-(4-methoxyphenyl)-2H-pyran

4-(tetrahydropyran-2-yloxy)benzaldehyde

3-(tetrahydro-2H-2-pyranyloxy)benzaldehyde

Refernces

Diastereoselective dihydroxylation and regioselective deoxygenation of dihydropyranones: A novel protocol for the stereoselective synthesis of C ₁-C₈ and C₁₅-C₂₁ subunits of (+)-discodermolide

10.1021/jo0492416

The study presents a novel protocol for the stereoselective synthesis of C1-C8 and C15-C21 subunits of (+)-discodermolide, a potent anti-cancer agent, through diastereoselective dihydroxylation and regioselective deoxygenation of dihydropyranones. Key chemicals used include R-pinene-based chiral "allyl"-borane reagents for introducing initial chirality, Grubbs's second-generation ruthenium catalyst for ring-closing metathesis reactions, OsO4/NMO for dihydroxylation, phenylchlorothionoformate and tributyltin hydride for regioselective deoxygenation, and various protecting groups and reagents for functional group transformations. These chemicals served the purpose of constructing the complex molecular structures of the subunits with high stereochemical control, which is crucial for their potential application in cancer treatment therapies.