alpha-Methyl-gamma-butyrolactone

Base Information

• Chemical Name: alpha-Methyl-gamma-butyrolactone
• CAS No.: 1679-47-6
• Molecular Formula: C5H8 O2
• Molecular Weight: 100.117
• Hs Code.: 2932209090
• European Community (EC) Number: 216-846-0
• NSC Number: 102837
• UNII: 140H0G0P5W
• DSSTox Substance ID: DTXSID401030919
• Nikkaji Number: J141.781I
• Wikidata: Q104253294
• Metabolomics Workbench ID: 46844
• ChEMBL ID: CHEMBL36365
• Mol file: 1679-47-6.mol

Synonyms:3-methyldihydrofuran-2(3H)-one;1679-47-6;alpha-Methyl-gamma-butyrolactone;3-methyloxolan-2-one;Dihydro-3-methyl-2(3H)-furanone;2-Methylbutanolide;2(3H)-Furanone, dihydro-3-methyl-;2-Methyl-4-butanolide;alpha-Methylbutyrolactone;.alpha.-Methylbutyrolactone;.alpha.-Methyl-.gamma.-butyrolactone;4-Hydroxy-2-methylbutyric acid lactone;2-methylbutyrolactone;4-Hydroxy-2-methylbutanoic acid lactone;2-Methyl-.gamma.-butyrolactone;2(3H)-Furanone, dihydromethyl-;3-methyldihydrofuran-2-one;4,5-Dihydro-3-methyl-2(3H)-furanone;3-methyltetrahydrofuran-2-one;3-Methyldihydro-2(3H)-furanone;140H0G0P5W;EINECS 216-846-0;MFCD00005396;NSC-102837;Gama-Valerolactone;methyl-butyrolactone;NSC102837;a-Methyl-g-butyrolactone;a-Methyl-?-butyrolactone;alpha -methylbutyrolactone;2-Methyl-gamma-butyrolactone;2-methyl-gamma-butyro-lactone;CHEMBL36365;SCHEMBL105334;UNII-140H0G0P5W;3-METHYL-2-OXOOXOLANE;3-Methyl-dihydro-furan-2-one;CHEBI:173343;DTXSID401030919;alpha -Methyl- gamma -butyrolactone;(+/-)-2-METHYLBUTYROLACTONE;AKOS015900293;alpha-Methyl-gamma-butyrolactone, 98%;NSC 102837;alpha -methyl-alpha -methylbutyrolactone;2-Methyl-laquo gammaRaquo -butyrolactone;SY051660;alpha -methyl-laquo gammaRaquo -butyrolactone;AM20090007;CS-0152675;FT-0622180;M1100;EN300-94873;D70164;(+/-)-DIHYDRO-3-METHYL-2(3H)-FURANONE;A882205;J-010416;(+/-)-.ALPHA.-METHYL-.GAMMA.-BUTYROLACTONE;alpha-Methyl-gamma-butyrolactone, purum, >=97.0% (GC);METHYL1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCURONATE;BUTYRIC ACID, 4-HYDROXY-2-METHYL-, .GAMMA.-LACTONE;BUTYRIC ACID, .GAMMA.-HYDROXY-.ALPHA.-METHYL-, .GAMMA.-LACTONE

Chemical Property of alpha-Methyl-gamma-butyrolactone

Chemical Property:

• Vapor Pressure: 0.386mmHg at 25°C
• Refractive Index: n20/D 1.432(lit.)
• Boiling Point: 197°Cat760mmHg
• Flash Point: 75°C
• PSA: 26.30000
• Density: 1.04g/cm³
• LogP: 0.56940
• Storage Temp.: 2-8°C
• Solubility.: THF: soluble
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 88.1

Purity/Quality:

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

3-Methyldihydrofuran-2(3H)-one ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Lactones
• Canonical SMILES: CC1CCOC1=O
• Uses: ALPHA-METHYL-GAMMA-BUTYROLACTONE was used as model compound in Bracketing experiments to investigate the thermodynamically favored site of reaction of pilocarpine. α-Methyl-γ-butyrolactone was used as model compound in Bracketing experiments to investigate the thermodynamically favored site of reaction of pilocarpine.

Technology Process of alpha-Methyl-gamma-butyrolactone

There total 88 articles about alpha-Methyl-gamma-butyrolactone 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: 87.0%

Dimethyl itakonate (617-52-7) → 3-methyltetrahydrofuran (13423-15-9) + dihydro-4-methyl-2(3H)-furanone (64190-48-3,65284-00-6,70470-05-2,1679-49-8) + 3-methyltetrahydro-2-furanone (1679-47-6)

Guidance literature:

With C₅₇H₆₉P₃Ru; hydrogen; bis(trifluoromethanesulfonyl)amide; at 200 ℃; for 0.0833333h; under 75007.5 Torr; Autoclave;

Reference yield: 30.0%

2-methylenesuccinic acid (97-65-4,25119-64-6) → dihydro-4-methyl-2(3H)-furanone (64190-48-3,65284-00-6,70470-05-2,1679-49-8) + 3-methyltetrahydro-2-furanone (1679-47-6) + 2-methylsuccinic anhydride (4100-80-5)

Guidance literature:

With 5% active carbon-supported ruthenium; hydrogen; at 150 ℃; under 26252.6 Torr;

DOI:10.1039/c0cc05206j

Reference yield: 23.0%

Dimethyl itakonate (617-52-7) → 3-methyltetrahydrofuran (13423-15-9) + dihydro-4-methyl-2(3H)-furanone (64190-48-3,65284-00-6,70470-05-2,1679-49-8) + methyl 2-methylsuccinate (21307-96-0,22644-27-5,63163-08-6,1604-11-1) + 3-methyltetrahydro-2-furanone (1679-47-6)

Guidance literature:

With C₄₅H₄₅P₃Ru; hydrogen; bis(trifluoromethanesulfonyl)amide; at 200 ℃; for 0.0833333h; under 75007.5 Torr; Autoclave;

upstream raw materials:

oxirane

2-acetylpropanoic acid ethyl ester

ethanol

potassium acetate

Downstream raw materials:

4-(2-methoxy-5-methyl-phenyl)-valeric acid

4-o-tolyloxy-valeric acid

4-(4-chloro-phenoxy)-valeric acid

4-(2,4,5-trichloro-phenoxy)-valeric acid

Refernces

• 1、 Gowda, Ravikumar R.,Chen, Eugene Y.-X.. "Regioselective Hydrogenation of Itaconic Acid to Γ-Isovalerolactone by Transition-Metal Nanoparticle Catalysts". . p. 973 - 977. Retrieved 2019.
• 2、 Boehrer, Gerald,Knorr, Rudolf. "TETRAKIS(1-METHYLCYCLOPROPYL)ETHYLENE IN FOUR STEPS FROM α-METHYL-γ-BUTYROLACTONE". . p. 3675 - 3678. Retrieved 1984.
• 3、 García Gutiérrez, José Luis,Jiménez-Cruz, Federico,Espinosa, Noé Rosas. "Synthesis of butyrolactones by nickel-catalyzed reductive cyanation of alkynols in water". . p. 803 - 805. Retrieved 2005.
• 4、 Spanjers, Charles S.,Schneiderman, Deborah K.,Wang, Jay Z.,Wang, Jingyu,Hillmyer, Marc A.,Zhang, Kechun,Dauenhauer, Paul J.. "Branched Diol Monomers from the Sequential Hydrogenation of Renewable Carboxylic Acids". . p. 3031 - 3035. Retrieved 2016.
• 5、 Torii, Sigeru,Inokuchi, Tsutomu,Kondo, Kazumi. "A Facile Procedure for Oxidative Cleavage of Enolic Olefins to the Carbonyl Compounds with Ruthenium Tetraoxide (RuO4)". . p. 4980 - 4982. Retrieved 1985.
• 6、 Sai, Yusuke,Sakakibara, Yoshimichi,Shigetomi, Kengo,Ubukata, Makoto,Uraki, Yasumitsu. "A NEW TEMPLATE of MITSUNOBU ACYLATE CLEAVABLE in NONALKALINE CONDITIONS". . p. 140 - 158. Retrieved 2022/01/08.