(3aR,6aS)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one

Base Information

• Chemical Name: (3aR,6aS)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one
• CAS No.: 43119-28-4
• Molecular Formula: C₇H₈O₂
• Molecular Weight: 124.139
• European Community (EC) Number: 610-106-4
• DSSTox Substance ID: DTXSID10349174
• Nikkaji Number: J28.180H
• Wikidata: Q72498170
• ChEMBL ID: CHEMBL505551
• Mol file: 43119-28-4.mol

Synonyms:43119-28-4;(3aR,6aS)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one;(3aR,6aS)-3,3a,6,6a-tetrahydrocyclopenta[b]furan-2-one;(1s,5r)-(-)-2-oxabicyclo[3.3.0]oct-6-en-3-one;26054-46-6;(1S,5R)-2-Oxabicyclo[3.3.0]oct-6-en-3-one;2H-cyclopenta[b]furan-2-one, 3,3a,6,6a-tetrahydro-, (3aR,6aS)-;(3aS,6aR)-rel-3,3a,6,6a-Tetrahydro-2H-cyclopenta[b]furan-2-one;(1S,5R)-(-)-cis-2-Oxabicyclo[3.3.0]oct-6-en-3-one;MFCD00010402;(3aS,6aR)-3,3a,6,6a-tetrahydrocyclopenta[b]furan-2-one;(1S,5R)-oxabicyclooctenone;CHEMBL505551;SCHEMBL3676033;DTXSID10349174;AKOS016843661;AC-26538;BS-17069;CS-0045251;F74043;A826161;J-502202;(1S,5R)-2-Oxabicyclo[3.3.0]oct-6-en-3-one, 99%;(R)-3,5,6,6a-Tetrahydro-2H-cyclopenta[b]furan-2-one;(3aR,6aS)-2H,3H,3aH,6H,6aH-cyclopenta[b]furan-2-one;(1S,5R)-2-Oxabicyclo[3.3.0]oct-6-en-3-one, puriss., >=99.0% (sum of enantiomers, GC)

Chemical Property of (3aR,6aS)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one

Chemical Property:

• Vapor Pressure: 0.0105mmHg at 25°C
• Melting Point: 44-46 °C(lit.)
• Refractive Index: 1.4906 (estimate)
• Boiling Point: 263.1oC at 760 mmHg
• Flash Point: 104oC
• PSA: 26.30000
• Density: 1.196g/cm3
• LogP: 0.87800
• Storage Temp.: 0-6°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 124.052429494
• Heavy Atom Count: 9
• Complexity: 172

Purity/Quality:

99% ^*data from raw suppliers

(1S,5R)-2-Oxabicyclo[3.3.0]oct-6-en-3-one 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C=CC2C1OC(=O)C2
• Isomeric SMILES: C1C=C[C@@H]2[C@H]1OC(=O)C2

Technology Process of (3aR,6aS)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one

There total 54 articles about (3aR,6aS)-3,3a,6,6a-tetrahydro-2H-cyclopenta[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: 100.0%

(3aS,6aR)-3,3-dichloro-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (162425-53-8) → (1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one (34638-25-0,38110-77-9,43119-28-4,54483-22-6,26054-46-6)

Guidance literature:

With ammonium chloride; zinc; In methanol; for 2h; Heating;

DOI:10.1016/S0040-4020(01)96154-X

Reference yield: 93.0%

(1S,5R)-(-)-bicyclo[3.2.0]hept-2-en-6-one (71155-04-9) → (1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one (34638-25-0,38110-77-9,43119-28-4,54483-22-6,26054-46-6)

Guidance literature:

With dihydrogen peroxide; acetic acid; at 0 ℃; for 12h;

DOI:10.1016/S0040-4039(00)97481-1

Reference yield: 68.0%

(3aR,5R,6aR)-(+)-5-Methansulfonsaeure-(2-oxo-hexahydro-2H-cyclopentafuran-5-yl)ester (151910-96-2) → (1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one (34638-25-0,38110-77-9,43119-28-4,54483-22-6,26054-46-6)

Guidance literature:

With pyridine; In benzene; at 240 - 250 ℃; for 0.5h;

upstream raw materials:

bicyclo(3.2.0)hept-2-en-6-one

(1S,5R)-(-)-bicyclo[3.2.0]hept-2-en-6-one

(1R,5S)-bicyclo[3.2.0]hept-2-en-6-one

bicyclo[3.2.0]hept-2-en-6-one

Downstream raw materials:

((3R,3aR,6aR)-2-Oxo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-3-yl)-acetic acid methyl ester

((1S,5R)-5-Hydroxy-cyclopent-2-enyl)-acetic acid

(1aS,2aR,5aR,5bR)-hexahydro-4H-oxireno[3,4]cyclopenta[1,2-b]furan-4-one

(3aR,4R,6R,6aR)-4-hydroxy-6-iodohexahydro-2H-cyclopenta[b]furan-2-one

Refernces

• 1、 Bianchi, Dario A.,Carabajal, María Ayelén,Ceccoli, Romina D.,Rial, Daniela V.. "Genome mining reveals new bacterial type I Baeyer-Villiger monooxygenases with (bio)synthetic potential". . . Retrieved 2020/03/19.
• 2、 Romero, Elvira,Castellanos, J. Rubén Gómez,Mattevi, Andrea,Fraaije, Marco W.. "Characterization and Crystal Structure of a Robust Cyclohexanone Monooxygenase". supporting information. p. 15852 - 15855. Retrieved 2016/12/16.