3-methylidene-4-octyl-4,6a-dihydro-3aH-furo[3,4-b]furan-2,6-dione

Base Information

• Chemical Name: 3-methylidene-4-octyl-4,6a-dihydro-3aH-furo[3,4-b]furan-2,6-dione
• CAS No.: 26057-70-5
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.337
• NSC Number: 179483
• DSSTox Substance ID: DTXSID70942302
• Nikkaji Number: J3.157.248G
• Mol file: 26057-70-5.mol

Synonyms:avenaciolide

Chemical Property of 3-methylidene-4-octyl-4,6a-dihydro-3aH-furo[3,4-b]furan-2,6-dione

Chemical Property:

• Vapor Pressure: 1.4E-08mmHg at 25°C
• Boiling Point: 458.2°Cat760mmHg
• Flash Point: 235.3°C
• PSA: 52.60000
• Density: 1.1g/cm³
• LogP: 2.76020
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 266.15180918
• Heavy Atom Count: 19
• Complexity: 374

Purity/Quality:

99% ^*data from raw suppliers

Avenaciolide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC1C2C(C(=O)O1)OC(=O)C2=C
• Description: Avenaciolide is a water-insoluble fungal metabolite originally isolated from A. avenaceus. It inhibits glutamate transport in isolated rat liver mitochondria (Ki = 8 μM).

Technology Process of 3-methylidene-4-octyl-4,6a-dihydro-3aH-furo[3,4-b]furan-2,6-dione

There total 55 articles about 3-methylidene-4-octyl-4,6a-dihydro-3aH-furo[3,4-b]furan-2,6-dione 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: 80.0%

(3aR,4S,6aR)-6-Hydroxy-3-methylene-4-octyl-tetrahydro-furo[3,4-b]furan-2-one → (+/-)-isoavenaciolide (16993-42-3,20223-76-1,26057-70-5,33644-09-6,50896-34-9,61474-24-6)

Guidance literature:

With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; In acetonitrile; Ambient temperature;

DOI:10.1016/0040-4020(95)00901-9

Reference yield: 65.0%

(S)-Hydroxy-((2R,3R)-4-methylene-2-octyl-5-oxo-tetrahydro-furan-3-yl)-acetic acid butyl ester → avenociolide (16993-42-3,20223-76-1,26057-70-5,33644-09-6,50896-34-9,61474-24-6) + isoavenociolide (16993-42-3,20223-76-1,26057-70-5,33644-09-6,50896-34-9,61474-24-6)

Guidance literature:

With toluene-4-sulfonic acid; In ⁽²⁾H₈-toluene; at 150 ℃; for 4h;

DOI:10.1021/jo991077c

Reference yield: 65.0%

(S)-Hydroxy-((2R,3R)-4-methylene-2-octyl-5-oxo-tetrahydro-furan-3-yl)-acetic acid butyl ester → avenociolide (16993-42-3,20223-76-1,26057-70-5,33644-09-6,50896-34-9,61474-24-6) + isoavenociolide (16993-42-3,20223-76-1,26057-70-5,33644-09-6,50896-34-9,61474-24-6)

Guidance literature:

With toluene-4-sulfonic acid; In ⁽²⁾H₈-toluene; at 150 ℃; for 4h;

DOI:10.1021/jo991077c

upstream raw materials:

(3aR,4R,6aR)-3-Methyl-4-octyl-3-phenylselanyl-dihydro-furo[3,4-b]furan-2,6-dione

5-octyl-5H-furan-2-one

2-((2R,3S,4S)-4-Iodo-2-octyl-5-oxo-tetrahydro-furan-3-yl)-2-phenylselanyl-propionic acid tert-butyl ester

nonan-1-al