6-Pentyl-2H-pyran-2-one

Base Information

• Chemical Name: 6-Pentyl-2H-pyran-2-one
• CAS No.: 27593-23-3
• Molecular Formula: C10H14O2
• Molecular Weight: 166.22
• Hs Code.: 2932999099
• European Community (EC) Number: 248-552-3
• NSC Number: 721361
• UNII: 8JTW8HL4PJ
• DSSTox Substance ID: DTXSID0047589
• Nikkaji Number: J47.697H
• Wikipedia: 6-Amyl-%CE%B1-pyrone
• Wikidata: Q27135350
• Metabolomics Workbench ID: 44679
• ChEMBL ID: CHEMBL503899
• Mol file: 27593-23-3.mol

Synonyms:6-pentyl-2H-pyran-2-one;6-pentylpyrone

Chemical Property of 6-Pentyl-2H-pyran-2-one

Chemical Property:

• Appearance/Colour: dairy aroma liquid
• Vapor Pressure: 0.00246mmHg at 25°C
• Melting Point: >230 °C
• Refractive Index: n20/D 1.505(lit.)
• Boiling Point: 287.6 °C at 760 mmHg
• Flash Point: 116.1 °C
• PSA: 30.21000
• Density: 1.003 g/cm³
• LogP: 2.37250
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 166.099379685
• Heavy Atom Count: 12
• Complexity: 214

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-Pentyl-2-pyrone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC1=CC=CC(=O)O1
• Description: 5-Hydroxy-2,4-decadienoic acid δ-lactone has a mushroom, bleu cheese lactone or dairy odor.
• Uses: 6-Pentyl-2-pyrone is an antifungal compound found in Trichoderma harzianum and may be important for cellular regulatory functions.

Technology Process of 6-Pentyl-2H-pyran-2-one

There total 20 articles about 6-Pentyl-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: 91.0%

6-pent-1-ynyl-pyran-2-one (24203-77-8) → 6-pentyl-2H-pyran-2-one (27593-23-3)

Guidance literature:

With hydrogen; Pd-BaSO₄; In toluene; at 20 ℃; under 760 Torr;

DOI:10.1016/S0040-4039(02)02600-X

Reference yield: 90.0%

2H-6-(trimethylsilyl)-5-butylpyranone → 6-pentyl-2H-pyran-2-one (27593-23-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(99)00182-9

Reference yield: 82.0%

dimethyl 2-butyl-2-(2-oxo-2H-pyran-6-yl)malonate → 6-pentyl-2H-pyran-2-one (27593-23-3)

Guidance literature:

With magnesium chloride hexahydrate; In N,N-dimethyl acetamide; at 140 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2017.01.063

upstream raw materials:

4-Decene-5-olide

(E)-1,1-bis(methylthio)-1,3-decadien-5-one

5-iodo-6-pentyl-2(2H)-pyranone

3-butynoic acid

Refernces

• 1、 Jones, Tappey H.,Fales, Henry M.. "E-6-(1-PENTENYL)-2H-PYRAN-2-ONE FROM CARPENTER ANTS (CAMPONOTUS SPP.)". . p. 5439 - 5440. Retrieved 1983.
• 2、 Wickel, Susanne M.,Citron, Christian A.,Dickschat, Jeroen S.. "2H-pyran-2-ones from trichoderma viride and trichoderma asperellum". . p. 2906 - 2913. Retrieved 2013/06/27.
• 3、 Dombray, Thomas,Blanc, Aurelien,Weibel, Jean-Marc,Pale, Patrick. "Gold(I)-catalyzed cycloisomerization of β-alkynylpropiolactones to substituted α-pyrones". supporting information; experimental part. p. 5362 - 5365. Retrieved 2011/02/27.