(3Z)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylidene]-4,8b-dihydro-3aH-indeno[1,2-b]furan-2-one

Base Information

• Chemical Name: (3Z)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylidene]-4,8b-dihydro-3aH-indeno[1,2-b]furan-2-one
• CAS No.: 80286-95-9
• Molecular Formula: C₁₇H₁₄O₅
• Molecular Weight: 298.295
• NSC Number: 289946
• DSSTox Substance ID: DTXSID10418531
• Nikkaji Number: J822.039E,J3.592.209A
• Mol file: 80286-95-9.mol

Synonyms:NSC289946;80286-95-9;SCHEMBL3479679;DTXSID10418531;GR-24;NSC-289946;J3.592.209A;(3E)-3-[[[(4-Methyl-5-oxo-2,5-dihydrofuran)-2-yl]oxy]methylene]-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one

Chemical Property of (3Z)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylidene]-4,8b-dihydro-3aH-indeno[1,2-b]furan-2-one

Chemical Property:

• Vapor Pressure: 6.66E-13mmHg at 25°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 298.08412354
• Heavy Atom Count: 22
• Complexity: 576

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(OC1=O)OC=C2C3CC4=CC=CC=C4C3OC2=O
• Isomeric SMILES: CC1=CC(OC1=O)O/C=C\2/C3CC4=CC=CC=C4C3OC2=O

Technology Process of (3Z)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylidene]-4,8b-dihydro-3aH-indeno[1,2-b]furan-2-one

There total 2 articles about (3Z)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylidene]-4,8b-dihydro-3aH-indeno[1,2-b]furan-2-one 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-bromo-4-methyl-2H-furan-5-one (59488-94-7) + C12H10O3 → rac-(3aR,8bS,E)-3-(((S)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl)oxymethylene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one + contalactone + rac. (3aR,8bS,5'R)-3-<<(2,5-dihydro-3-methyl-2-oxo-5-furanyl)oxo>methylene>-3,3a,4,8b-tetrahydroindeno<1,2-b>furan-2-one (76974-79-3,78647-00-4,80286-95-9)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1016/j.phytochem.2019.112112

Reference yield:

2-bromo-4-methyl-2H-furan-5-one (59488-94-7) + Methyl formate (107-31-3) + cis-3,3a,4,8b-tetrahydro-2H-indeno<1,2-b>furan-2-one (4471-33-4,70667-72-0,78646-74-9) → rac-(3aR,8bS,E)-3-(((S)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl)oxymethylene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one + rac. (3aR,8bS,5'R)-3-<<(2,5-dihydro-3-methyl-2-oxo-5-furanyl)oxo>methylene>-3,3a,4,8b-tetrahydroindeno<1,2-b>furan-2-one (76974-79-3,78647-00-4,80286-95-9)

Guidance literature:

Methyl formate; cis-3,3a,4,8b-tetrahydro-2H-indeno<1,2-b>furan-2-one; With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

2-bromo-4-methyl-2H-furan-5-one; In 1,2-dimethoxyethane; Inert atmosphere;

DOI:10.1016/j.tet.2010.06.072

upstream raw materials:

2-bromo-4-methyl-2H-furan-5-one

Methyl formate

cis-3,3a,4,8b-tetrahydro-2H-indeno<1,2-b>furan-2-one