3,4-Dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid

Base Information

• Chemical Name: 3,4-Dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid
• CAS No.: 80866-93-9
• Molecular Formula: C8H10 O4
• Molecular Weight: 170.165
• Hs Code.: 2932999099
• European Community (EC) Number: 279-596-1
• DSSTox Substance ID: DTXSID20230761
• Nikkaji Number: J236.501D
• Wikidata: Q83111469
• Mol file: 80866-93-9.mol

Synonyms:80866-93-9;3,4-Dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid;2,2-Dimethyl-4-oxo-3,4-dihydro-2H-pyran-6-carboxylic acid;2,2-dimethyl-4-oxo-3H-pyran-6-carboxylic acid;BRN 0121772;EINECS 279-596-1;2H-Pyran-6-carboxylic acid, 3,4-dihydro-2,2-dimethyl-4-oxo-;4H-Pyran-2-carboxylic acid, 5,6-dihydro-6,6-dimethyl-4-oxo-;5,6-Dihydro-6,6-dimethyl-4-oxo-4H-pyran-2-carboxylic acid;Acide dimethyl-6,6 dihydro-5,6 pyrone-4 carboxylique-2 [French];2-18-00-00320 (Beilstein Handbook Reference);Acide dimethyl-6,6 dihydro-5,6 pyrone-4 carboxylique-2;SCHEMBL2113918;DTXSID20230761;STR05224;STL512790;AKOS015955336;LS-127282;CS-0322414;FT-0641786;A915834;2,2-Dimethyl-4-oxo-3,4-dihydro-2H-pyran-6-carboxylicacid;2,2-Dimethyl-4-oxo-3,4-dihydro-2H-pyran-6-carboxylic acid #;3,4-Dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid, 98%

Chemical Property of 3,4-Dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid

Chemical Property:

• Vapor Pressure: 0.004mmHg at 25°C
• Melting Point: 170 °C (dec.)(lit.)
• Refractive Index: 1.4425 (estimate)
• Boiling Point: 259ºC at 760 mmHg
• Flash Point: 102.4ºC
• PSA: 63.60000
• Density: 1.1456 (rough estimate)
• LogP: 0.72290
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 170.05790880
• Heavy Atom Count: 12
• Complexity: 262

Purity/Quality:

97% ^*data from raw suppliers

3,4-Dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC(=O)C=C(O1)C(=O)O)C
• Uses: 3,4-Dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid was used as photoprotective reagent during photolysis of the Salmonella sialidase.

Technology Process of 3,4-Dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid

There total 5 articles about 3,4-Dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid 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: 80.0%

ethyl 2,2-dimethyl-4-oxo-3,4-dihydro-2H-pyran-6-carboxylate (5464-36-8) → 3,4-dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid (80866-93-9)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; Inert atmosphere;

DOI:10.1021/acs.joc.6b01066

Reference yield: 53.0%

hydroxy-2 oxo-4 methyl-6 heptadiene-2,5 oate de methyle (108097-78-5) → 3,4-dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid (80866-93-9)

Guidance literature:

With hydrogenchloride; In acetic acid; for 1h; Heating;

Reference yield:

4-methyl-pent-3-en-2-one (141-79-7) → 3,4-dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid (80866-93-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ethanol / 0.08 h / 0 °C / Inert atmosphere

1.2: 20.5 h / 0 - 20 °C / Inert atmosphere

2.1: hydrogenchloride / water; tetrahydrofuran / Inert atmosphere

With hydrogenchloride; In tetrahydrofuran; ethanol; water;

DOI:10.1021/acs.joc.6b01066

upstream raw materials:

hydroxy-2 oxo-4 methyl-6 heptadiene-2,5 oate de methyle

hydrogenchloride

4-methyl-pent-3-en-2-one

ethyl 2,2-dimethyl-4-oxo-3,4-dihydro-2H-pyran-6-carboxylate

Downstream raw materials:

2,2-Dimethyl-6-(2-phenyl-oxazolidine-3-carbonyl)-2,3-dihydro-pyran-4-one

6,6-Dimethyl-4-oxo-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl-isopropyl-amide

6,6-Dimethyl-4-oxo-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl-methyl-amide

6,6-Dimethyl-4-oxo-5,6-dihydro-4H-pyran-2-carboxylic acid dibenzylamide