2H-Cyclopenta[b]furan-4-carboxaldehyde, hexahydro-2-oxo-, [3aR-(3aalpha,4alpha,6aalpha)]- (9CI)

Base Information

• Chemical Name: 2H-Cyclopenta[b]furan-4-carboxaldehyde, hexahydro-2-oxo-, [3aR-(3aalpha,4alpha,6aalpha)]- (9CI)
• CAS No.: 201421-82-1
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• Mol file: 201421-82-1.mol

Synonyms:2H-Cyclopenta[b]furan-4-carboxaldehyde, hexahydro-2-oxo-, [3aR-(3aalpha,4alpha,6aalpha)]- (9CI)

Chemical Property of 2H-Cyclopenta[b]furan-4-carboxaldehyde, hexahydro-2-oxo-, [3aR-(3aalpha,4alpha,6aalpha)]- (9CI)

Chemical Property:

• PSA: 43.37000
• LogP: 0.52700

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2H-Cyclopenta[b]furan-4-carboxaldehyde, hexahydro-2-oxo-, [3aR-(3aalpha,4alpha,6aalpha)]- (9CI)

There total 20 articles about 2H-Cyclopenta[b]furan-4-carboxaldehyde, hexahydro-2-oxo-, [3aR-(3aalpha,4alpha,6aalpha)]- (9CI) 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: 99.0%

(3aR,4R,6aS)-4-((E)-Styryl)-hexahydro-cyclopenta[b]furan-2-one → <3aα,4α6aα>-hexahydro-2-oxo-2H-cyclopenta furan-4-carboxaldehyde (201421-82-1)

Guidance literature:

(3aR,4R,6aS)-4-((E)-Styryl)-hexahydro-cyclopenta[b]furan-2-one; With ozone; In dichloromethane;

With 2,3-dimercapto-succinic acid; In dichloromethane;

DOI:10.1055/s-2004-835637

Reference yield: 50.0%

(1S,5R,6R)-6-hydroxymethyl-3-oxo-2-oxabicyclo<3.3.0>octane (111056-88-3) → <3aα,4α6aα>-hexahydro-2-oxo-2H-cyclopenta furan-4-carboxaldehyde (201421-82-1)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 ℃; 1.) 15 min; 2.) 0.5 h;

DOI:10.1248/cpb.34.4629

Reference yield:

(1S,4R,5R)-4-hydroxymethyl-8-methylbicyclo<3.3.0>oct-7-en-2-one (110943-02-7) → <3aα,4α6aα>-hexahydro-2-oxo-2H-cyclopenta furan-4-carboxaldehyde (201421-82-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 95 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 2 h / 30 °C

2: 79 percent / NaBH₄ / methanol / 0.5 h / -10 °C

3: 80 percent / pyridine / CH₂Cl₂ / 6 h / Ambient temperature

5: 79 percent / Jones reagent / acetone / 0.5 h / -10 °C

6: 87 percent / 5percent Pd/C / methanol / Ambient temperature

7: 96 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

8: 78 percent / 80percent MCPBA, NaHCO₃ / CH₂Cl₂ / 5 h / Ambient temperature

9: KOH / methanol; H₂O / 2 h / Ambient temperature

10: 1.) triphenylphosphine, DEAD; 2.) TiCl₄ / 1.) benzene, 5-10 deg C, 3 h; 2.) methylene dichloride, 0 deg C, 1 h

11: 50 percent / 1.) DMSO, oxalyl chloride; 2.) triethylamine / CH₂Cl₂ / -60 °C / 1.) 15 min; 2.) 0.5 h

With pyridine; potassium hydroxide; sodium tetrahydroborate; jones reagent; oxalyl dichloride; titanium tetrachloride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In methanol; dichloromethane; water; acetone;

DOI:10.1248/cpb.34.4629

upstream raw materials:

(1S,5S)-3-oxo-2-oxabicyclo<3.3.0>oct-6-en-6-carbaldehyde

(1S,5R,6R)-6-hydroxymethyl-3-oxo-2-oxabicyclo<3.3.0>octane

cyclopent-2-enol

cyclopent-2-enone

Downstream raw materials:

(1S,5R,6S)-6-hydroxymethyl-3-oxo-2-oxabicyclo<3.3.0>octane