alpha-Methylene-gamma-valerolactone

Base Information

• Chemical Name: alpha-Methylene-gamma-valerolactone
• CAS No.: 62873-16-9
• Molecular Formula: C6H8O2
• Molecular Weight: 112.128
• Hs Code.: 2932209090
• European Community (EC) Number: 613-095-4
• NSC Number: 272654
• DSSTox Substance ID: DTXSID401291985
• Nikkaji Number: J1.655.762E
• ChEMBL ID: CHEMBL8590
• Mol file: 62873-16-9.mol

Synonyms:62873-16-9;alpha-Methylene-gamma-valerolactone;5-methyl-3-methylideneoxolan-2-one;alpha-Methylene-gamma-valerolactone (stabilized with HQ);5-methyl-3-methylenedihydrofuran-2(3H)-one;5-Methyl-3-methylene-dihydro-furan-2-one;gamma-methyl-alpha-methylene-gamma-butyrolactone;2(3H)-Furanone, dihydro-5-methyl-3-methylene-;4,5-Dihydro-5-methyl-3-methylene-2(3H)-furanone;5-methyl-3-methylidene-oxolan-2-one;5-Methyl-3-methylenedihydro-2(3H)-furanone;NSC272654;CHEMBL8590;SCHEMBL311139;a-methylene-gamma-valerolactone;DTXSID401291985;GEO-04344;MFCD06797118;AKOS015908040;NSC 272654;NSC-272654;Dihydro-3-methylene-5-methyl-2-furanone;FT-0641502;FT-0650613;M1453;5-Methyl-3-methylenedihydro-2(3H)-furanone #;D91504

Chemical Property of alpha-Methylene-gamma-valerolactone

Chemical Property:

• Vapor Pressure: 0.122mmHg at 25°C
• Refractive Index: 1.451
• Boiling Point: 219.015 °C at 760 mmHg
• Flash Point: 81.488 °C
• PSA: 26.30000
• Density: 1.036 g/cm³
• LogP: 0.87800
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 112.052429494
• Heavy Atom Count: 8
• Complexity: 138

Purity/Quality:

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

α-Methylene-γ-valerolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(=C)C(=O)O1

Technology Process of alpha-Methylene-gamma-valerolactone

There total 45 articles about alpha-Methylene-gamma-valerolactone 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: 88.0%

carbon monoxide (201230-82-2) + 4-bromopent-4-en-2-ol (82112-57-0) → 5-methyl-3-(methylidene)dihydrofuran-2(5H)-one (62873-16-9)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In acetonitrile; at 70 ℃; for 48h; under 1654.9 - 1810.02 Torr;

DOI:10.1021/jo00140a007

Reference yield: 87.0%

ethyl 2-methylidenepent-4-enoate (54109-49-8) → 5-methyl-3-(methylidene)dihydrofuran-2(5H)-one (62873-16-9)

Guidance literature:

With sulfuric acid; for 1h; cooling;

DOI:10.1055/s-2005-870025

Reference yield: 82.0%

2-methylidenepent-4-enoic acid (4743-96-8) → 5-methyl-3-(methylidene)dihydrofuran-2(5H)-one (62873-16-9)

Guidance literature:

With calcium(II) bis(trifluoromethanesulfonyl)imide; tert-butylammonium hexafluorophosphate(V); at 80 ℃; for 20h; Sealed tube;

DOI:10.1021/acs.orglett.9b02705

upstream raw materials:

4,5-dihydro-3-(hydroxymethyl)-5-methylfuran-2(3H)-one

formaldehyd

5-methyl-3-(triphenyl-λ⁵-phosphanylidene)-dihydro-furan-2-one

(2-oxo-5-methyltetrahydrofuran-3-yl)-phosphonic acid diethyl ester