2(5H)-Furanone,5-[[(1R,6S,7S,8S)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-dien-7-yl]methylene]-,(5E)-(9CI)

Base Information

• Chemical Name: 2(5H)-Furanone,5-[[(1R,6S,7S,8S)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-dien-7-yl]methylene]-,(5E)-(9CI)
• CAS No.: 819077-13-9
• Molecular Formula: C14H14 O3
• Molecular Weight: 230.263
• Mol file: 819077-13-9.mol

Synonyms:(E)-1893A

Chemical Property of 2(5H)-Furanone,5-[[(1R,6S,7S,8S)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-dien-7-yl]methylene]-,(5E)-(9CI)

Chemical Property:

• PSA: 35.53000
• LogP: 2.12900

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2(5H)-Furanone,5-[[(1R,6S,7S,8S)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-dien-7-yl]methylene]-,(5E)-(9CI)

There total 1 articles about 2(5H)-Furanone,5-[[(1R,6S,7S,8S)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-dien-7-yl]methylene]-,(5E)-(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:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) → 5-[1-((1R,6S,7S,8S)-8-Methyl-9-oxa-bicyclo[4.2.1]nona-2,4-dien-7-yl)-meth-(E)-ylidene]-5H-furan-2-one (819077-13-9)

Guidance literature:

Multi-step reaction with 20 steps

1: LiAlH₄ / tetrahydrofuran / 20 h / 0 °C

2: 2.92 g / pyridine / 17 h / 20 °C

3: lipase PS (Amano); H₂O / tetrahydrofuran / 480 h / 20 °C

4: imidazole / dimethylformamide / 23 h / 0 °C

5: 1.90 g / NaOMe / methanol / 2 h / 20 °C

6: 96 percent / NaH / tetrahydrofuran / 2 h / 0 °C

7: 85 percent / OsO₄; H₂O; Me₃NO*2H₂O / acetone; 2-methyl-propan-2-ol / 20 h / 0 °C

8: 89 percent / n-Bu₃SnH; AIBN / toluene / 1 h / Heating

9: Pb(OAc)4 / benzene / 0.75 h / 20 °C

10: 2.04 g / NaBH₄ / methanol / 1 h / 20 °C

11: 79 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

12: 96 percent / NaI / butan-2-one / 12 h / Heating

13: 89 percent / benzene; tetrahydrofuran / 20 h / 20 °C

14: 86 percent / [1,3-dimesitylimidazolidin-2-yl]Cl₂(PCy₃)Ru=CHPh / benzene / 6 h / Heating

15: 96 percent / Br₂ / diethyl ether / 1 h / -78 °C

16: 53 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 75 °C

17: 100 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 0 °C

18: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

19: 24.5 mg / TESOTf / CH₂Cl₂ / 1 h / -78 °C

20: 13 percent / MsCl; pyridine / 48 h / 80 °C

With pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lead(IV) acetate; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); trimethylamine-N-oxide; Lipase PS (Amano); potassium tert-butylate; tetrabutyl ammonium fluoride; water; bromine; tri-n-butyl-tin hydride; triethylsilyl trifluoromethyl sulfonate; sodium methylate; sodium hydride; Dess-Martin periodane; methanesulfonyl chloride; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; butanone; tert-butyl alcohol; benzene; 18: Dess-Martin oxidation;

DOI:10.1021/jo048566j

upstream raw materials:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride