Methanone, 2-furanyl[(1R,6S,7R,8S)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-dien-7-yl]- (9CI)

Base Information

Chemical Name:Methanone, 2-furanyl[(1R,6S,7R,8S)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-dien-7-yl]- (9CI)
CAS No.:817201-27-7
Molecular Formula:C14H14 O3
Molecular Weight:230.263
Hs Code.:
Mol file:817201-27-7.mol

Synonyms:Methanone, 2-furanyl[(1R,6S,7R,8S)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-dien-7-yl]- (9CI)

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Methanone, 2-furanyl[(1R,6S,7R,8S)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-dien-7-yl]- (9CI)

Chemical Property:

PSA：39.44000
LogP:2.60800

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of Methanone, 2-furanyl[(1R,6S,7R,8S)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-dien-7-yl]- (9CI)

There total 29 articles about Methanone, 2-furanyl[(1R,6S,7R,8S)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-dien-7-yl]- (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: 72.0%

: (1R,6S,7S,8S)-7-[1-(2-furyl)-1-hydroxymethyl]-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene

: 817201-27-7
(1R,6S,7R,8S)-7-(furan-2-carbonyl)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene

Guidance literature:: With manganese(IV) oxide; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/jo048566j

Reference yield:

: 6118-51-0
exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

: 817201-27-7
(1R,6S,7R,8S)-7-(furan-2-carbonyl)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene

Guidance literature:: Multi-step reaction with 21 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: NaClO₂; NH₂SO₃H; Na₂HPO₄ / H₂O; 2-methyl-propan-2-ol / 0.5 h / 20 °C

20: Et₃N; DMAP; 1-hydroxybenzotriazol / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 16 h / 20 °C

21: 12.8 mg / tetrahydrofuran / 0.67 h / 0 °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; dmap; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); trimethylamine-N-oxide; Lipase PS (Amano); aminosulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; bromine; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; benzotriazol-1-ol; Dess-Martin periodane; triethylamine; sodium iodide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; butanone; tert-butyl alcohol; benzene; 18: Dess-Martin oxidation;
DOI:10.1021/jo048566j

Reference yield:

: 106137-27-3,817201-06-2
exo-2,3-bis(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-ene

: 817201-27-7
(1R,6S,7R,8S)-7-(furan-2-carbonyl)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene

Guidance literature:: Multi-step reaction with 20 steps

1: 2.92 g / pyridine / 17 h / 20 °C

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

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

4: 1.90 g / NaOMe / methanol / 2 h / 20 °C

5: 96 percent / NaH / tetrahydrofuran / 2 h / 0 °C

6: 85 percent / OsO₄; H₂O; Me₃NO*2H₂O / acetone; 2-methyl-propan-2-ol / 20 h / 0 °C

7: 89 percent / n-Bu₃SnH; AIBN / toluene / 1 h / Heating

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

9: 2.04 g / NaBH₄ / methanol / 1 h / 20 °C

10: 79 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

11: 96 percent / NaI / butan-2-one / 12 h / Heating

12: 89 percent / benzene; tetrahydrofuran / 20 h / 20 °C

13: 86 percent / [1,3-dimesitylimidazolidin-2-yl]Cl₂(PCy₃)Ru=CHPh / benzene / 6 h / Heating

14: 96 percent / Br₂ / diethyl ether / 1 h / -78 °C

15: 53 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 75 °C

16: 100 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 0 °C

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

18: NaClO₂; NH₂SO₃H; Na₂HPO₄ / H₂O; 2-methyl-propan-2-ol / 0.5 h / 20 °C

19: Et₃N; DMAP; 1-hydroxybenzotriazol / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 16 h / 20 °C

20: 12.8 mg / tetrahydrofuran / 0.67 h / 0 °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; dmap; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; osmium(VIII) oxide; n-butyllithium; 2,2'-azobis(isobutyronitrile); trimethylamine-N-oxide; Lipase PS (Amano); aminosulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; bromine; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; benzotriazol-1-ol; Dess-Martin periodane; triethylamine; sodium iodide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; butanone; tert-butyl alcohol; benzene; 17: Dess-Martin oxidation;
DOI:10.1021/jo048566j