(S)-5-methylfuran-2(5H)-one

Base Information

• Chemical Name: (S)-5-methylfuran-2(5H)-one
• CAS No.: 92694-51-4
• Molecular Formula: C5H6O2
• Molecular Weight: 98.09990
• UNII: ZA9THM6FSR
• Metabolomics Workbench ID: 55372
• Nikkaji Number: J432.703I
• Wikidata: Q27116836
• Mol file: 92694-51-4.mol

Synonyms:(S)-5-methylfuran-2(5H)-one;(2S)-2-methyl-2H-furan-5-one;(5S)-5-methylfuran-2(5H)-one;ZA9THM6FSR;92694-51-4;CHEBI:36444;(S)-5-methyl-2(5H)-furanone;BGLUXFNVVSVEET-BYPYZUCNSA-N;(5S)-5-Methyl-2(5H)-furanone;(5S)-5-Methyl-2,5-dihydrofuran-2-one;Q27116836

Chemical Property of (S)-5-methylfuran-2(5H)-one

Chemical Property:

• Boiling Point: 40-42 °C(Press: 1.3 Torr)
• PSA: 26.30000
• Density: 1.095±0.06 g/cm3(Predicted)
• LogP: 0.48790
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 98.036779430
• Heavy Atom Count: 7
• Complexity: 115

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C=CC(=O)O1
• Isomeric SMILES: C[C@H]1C=CC(=O)O1

Technology Process of (S)-5-methylfuran-2(5H)-one

There total 1 articles about (S)-5-methylfuran-2(5H)-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:

5-methyl-5H-furan-2-one (591-11-7) + N-(tert-butoxycabonyl)-N-(4-methoxyphenyl)-3-phenyl-(E)-2-propen-1-amine → (R)-β-angelica lactone (62322-48-9) + (S)-(+)-β-angelica lactone (92694-51-4) + (3S,2'S,3''R)-(4-methoxy-phenyl)-[3-(2'-methyl-5-oxo-tetrahydro-furan-3-yl)-3''-phenyl-poropenyl]-carbamic acid tert-butyl ester + (3R,2'R,3''S)-(4-methoxy-phenyl)-[3-(2'-methyl-5-oxo-tetrahydro-furan-3-yl)-3''-phenyl-propenyl]-carbamic acid tert-butyl ester

Guidance literature:

N-(tert-butoxycabonyl)-N-(4-methoxyphenyl)-3-phenyl-(E)-2-propen-1-amine; With n-butyllithium; (-)-sparteine; In toluene; at -78 ℃; for 0.5h;

5-methyl-5H-furan-2-one; With chloro-trimethyl-silane; In toluene; for 1h;

With tetrabutyl ammonium fluoride; In methanol; toluene; at 20 ℃; for 0.5h; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/ol0263898

Reference yield: 100.0%

(S)-(+)-β-angelica lactone (92694-51-4) → (S)-γ-valerolactone (19041-15-7)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethyl acetate; for 5h;

DOI:10.1134/S1070428008120142

Reference yield:

(S)-(+)-β-angelica lactone (92694-51-4) → (1S,3S,3aS,4R,4aS,8aR,9aS)-1-Methoxy-3-methyl-4-phenylsulfanylmethyl-dodecahydro-naphtho[2,3-c]furan (192133-37-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: lithium perchlorate / diethyl ether / 168 h / 20 °C

2.1: 96 percent / H₂ / 10 percent Pd/C / ethanol / 12 h / 20 °C / 760 Torr

3.1: 92 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C

4.1: 83 percent / DBU / toluene / 5 h / 100 °C

5.1: 96 percent / H₂ / PtO₂ / ethanol / 16 h / 20 °C / 760 Torr

6.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

7.1: 1.50 g / BF₃*Et₂O / CH₂Cl₂ / 12 h / -60 °C

8.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 20 °C

9.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C

9.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C

10.1: BH₃*THF / tetrahydrofuran / 3 h / -78 °C

10.2: 73 percent / aq. NaOH; H₂O₂ / 0.5 h / 0 °C

11.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 0 °C

12.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C

With dmap; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; lithium perchlorate; sodium hexamethyldisilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 1.1: Diels-Alder reaction / 9.2: Wittig reaction;

DOI:10.1016/S0040-4020(02)01358-3

upstream raw materials:

5-methyl-5H-furan-2-one

Downstream raw materials:

(3S,4R,5S)-4-(dimethylphenylsilyl)-3-hexyl-4,5-dihydro-5-methyl-2(3H)-furanone

(3S,4R,5S)-3-butyl-4-(dimethylphenylsilyl)-4,5-dihydro-5-methyl-2(3H)-furanone

(3S,4R,5S)-4-(dimethylphenylsilyl)-4,5-dihydro-5-methyl-3-(5-methylhexyl)-2(3H)-furanone

(+)-epolactaene