2(3H)-Furanone,4-dimethyl-

Base Information

• Chemical Name: 2(3H)-Furanone,4-dimethyl-
• CAS No.: 510-18-9
• Molecular Formula: C10H14 O5
• Molecular Weight: 214.218
• Hs Code.: 2932190090
• NSC Number: 350598
• DSSTox Substance ID: DTXSID30965274
• Nikkaji Number: J33.404I
• Wikidata: Q77490658
• Metabolomics Workbench ID: 109715
• Mol file: 510-18-9.mol

Synonyms:NSC350598;NSC-350598;2(3H)-Furanone,4-dimethyl-;SCHEMBL3796861;DTXSID30965274;4-Acetyl-3,4-dimethyl-5-oxooxolan-2-yl acetate

Chemical Property of 2(3H)-Furanone,4-dimethyl-

Chemical Property:

• Vapor Pressure: 0.000114mmHg at 25°C
• Melting Point: 115-116℃ (methanol )
• Boiling Point: 336.2°Cat760mmHg
• Flash Point: 148.9°C
• PSA: 69.67000
• Density: 1.18g/cm³
• LogP: 0.66380
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 214.08412354
• Heavy Atom Count: 15
• Complexity: 322

Purity/Quality:

98%min ^*data from raw suppliers

Acetomycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(OC(=O)C1(C)C(=O)C)OC(=O)C
• Uses: Acetomycin is an anti-biotic, anti-fungal, anti-protozoal, and anti-bacterial agent.

Technology Process of 2(3H)-Furanone,4-dimethyl-

There total 91 articles about 2(3H)-Furanone,4-dimethyl- 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: 90.0%

(2S,3S,4R)-4-acetoxy-4-hydroxy-2-<(1R)-1-hydroxyethyl>-2,3-dimethylbutanoic acid γ-lactone (103560-91-4) → (-)-Acetomycin (510-18-9)

Guidance literature:

With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1021/jo00040a014

Reference yield: 83.0%

Acetic acid (2S,3R,4R)-4-(1-hydroxy-ethyl)-3,4-dimethyl-5-oxo-tetrahydro-furan-2-yl ester (103560-90-3,103560-91-4,129519-20-6,141585-63-9,141585-64-0) → (+/-)-acetomycin (510-18-9,136520-27-9,136520-28-0,138750-96-6,138750-97-7,141660-81-3,141660-82-4,141660-83-5)

Guidance literature:

With jones reagent;

DOI:10.1016/S0040-4039(00)92712-6

Reference yield: 82.0%

Acetic acid (2R,3S,4S)-3,4-dimethyl-4-(2-methyl-[1,3]dioxolan-2-yl)-5-oxo-tetrahydro-furan-2-yl ester → (-)-Acetomycin (510-18-9)

Guidance literature:

With toluene-4-sulfonic acid; In acetone;

DOI:10.1002/ejoc.200300504

upstream raw materials:

(2S,3S,4R)-4-acetoxy-4-hydroxy-2-<(1R)-1-hydroxyethyl>-2,3-dimethylbutanoic acid γ-lactone

(3S,4S,5R)-3,5-Diacetyl-3,4-dimethyl-dihydro-furan-2-one

(3R)(4S)(5R)-5-acetoxy-3-acetyl-3-(1,3-dithianyl)-4-methyl-dihydro-2(3H)-furanone

2-methyl-acetoacetic acid methyl ester

Downstream raw materials:

2,3-dimethylcyclopent-2-enone

Refernces

• 1、 Uenishi, Jun'ichi,Kawatsura, Motoi,Ikeda, Daiji,Muraoka, Nobuhiro. "Construction of Consecutive Chiral Non-Racemic Quaternary and Tertiary Carbon Centers: A Short Synthetic Route to (-)-Acetomycin". . p. 3909 - 3912. Retrieved 2007/10/03.
• 2、 Sprules, Tara J.,Lavallee, Jean-Francois. "Unexpected Contrasteric Alkylation Leading to a Model for Five-Membered Ring Enolate Alkylation: Short Stereoselective Synthesis of (+/-)-Acetomycin". . p. 5041 - 5047. Retrieved 2007/10/02.