2-Methylene-3(2H)-furanone

Base Information

• Chemical Name: 2-Methylene-3(2H)-furanone
• CAS No.: 92544-22-4
• Molecular Formula: C5H4 O2
• Molecular Weight: 96.0856
• DSSTox Substance ID: DTXSID80239038
• Nikkaji Number: J2.387.037A
• Wikidata: Q83121381
• Mol file: 92544-22-4.mol

Synonyms:2-MEFUE;2-methylene-3(2H)-furanone

Chemical Property of 2-Methylene-3(2H)-furanone

Chemical Property:

• Vapor Pressure: 0.0861mmHg at 25°C
• Boiling Point: 225.5°Cat760mmHg
• Flash Point: 112.5°C
• Density: 1.14g/cm³
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 96.021129366
• Heavy Atom Count: 7
• Complexity: 144

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C1C(=O)C=CO1

Technology Process of 2-Methylene-3(2H)-furanone

There total 9 articles about 2-Methylene-3(2H)-furanone 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:

2'-deoxy-2'-chloroguanosine-5'-triphosphate (1428903-51-8) → 2-amino-1,9-dihydro-6H-purin-6-one (73-40-5) + 2-methylene-3(2H)-furanone (92544-22-4)

Guidance literature:

With sodium dithionite; radical S-adenosylmethionine (AdoMet) enzyme; AdoMet; In water; for 5h; Enzymatic reaction;

DOI:10.1021/ja502663k

Reference yield:

9-<3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-trifluoromethanesulfonyl-β-D-arabino-furanosyl>guanine (221092-58-6) → 2-amino-1,9-dihydro-6H-purin-6-one (73-40-5) + 2-methylene-3(2H)-furanone (92544-22-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium chloride / N,N-dimethyl-formamide / 20 - 50 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C

3.1: trimethyl phosphite / 0.25 h / 50 °C

3.2: 1.5 h / 0 °C

4.1: NDP kinase; guanylate kinase; ATP / water / Enzymatic reaction

5.1: radical S-adenosylmethionine (AdoMet) enzyme; AdoMet; sodium dithionite / water / 5 h / Enzymatic reaction

With trimethyl phosphite; sodium dithionite; guanylate kinase; radical S-adenosylmethionine (AdoMet) enzyme; NDP kinase; AdoMet; tetrabutyl ammonium fluoride; ATP; lithium chloride; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/ja502663k

Reference yield:

3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-chloro-2'-deoxy-β-D-guanosine → 2-amino-1,9-dihydro-6H-purin-6-one (73-40-5) + 2-methylene-3(2H)-furanone (92544-22-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C

2.1: trimethyl phosphite / 0.25 h / 50 °C

2.2: 1.5 h / 0 °C

3.1: NDP kinase; guanylate kinase; ATP / water / Enzymatic reaction

4.1: radical S-adenosylmethionine (AdoMet) enzyme; AdoMet; sodium dithionite / water / 5 h / Enzymatic reaction

With trimethyl phosphite; sodium dithionite; guanylate kinase; radical S-adenosylmethionine (AdoMet) enzyme; NDP kinase; AdoMet; tetrabutyl ammonium fluoride; ATP; In tetrahydrofuran; water;

DOI:10.1021/ja502663k

upstream raw materials:

2'-deoxy-2'-chloroguanosine-5'-triphosphate

9-<3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-trifluoromethanesulfonyl-β-D-arabino-furanosyl>guanine

2'-chloro-2'-deoxyguanosine

2'-chloro-2'-deoxyguanosine-5'-monophosphate

Refernces