(1R,4aS,8aS)-(-)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene

Base Information

• Chemical Name: (1R,4aS,8aS)-(-)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene
• CAS No.: 108944-91-8
• Molecular Formula: C₂₂H₃₂O₃
• Molecular Weight: 344.494
• Mol file: 108944-91-8.mol

Synonyms:(1R,4aS,8aS)-(-)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene

Chemical Property of (1R,4aS,8aS)-(-)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4aS,8aS)-(-)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene

There total 10 articles about (1R,4aS,8aS)-(-)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene 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:

trans geranyl acetone (3796-70-1) → (1R,4aS,8aS)-(-)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene (108944-91-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 88 percent / NaH / diethyl ether / 8 h / Heating

2: 32.1 percent / SnCl₄, H₂O / CH₂Cl₂ / Ambient temperature

3: 96.1 percent / NaBH₄ / methanol / 5.5 h / -60 - -40 °C

4: 43.2 percent / 20 h / 80 - 90 °C

5: 60.3 percent / Et₃N, HSiCl₃ / benzene / 7 h / Heating

6: 87.4 percent / LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

7: 79.3 percent / pyridine / 18 h / 0 °C

8: 91.4 percent / CrO₃ / acetone / 0 degC, 10 min; r.t., 30 min

9: 96.8 percent / DBU / benzene / 12 h / Ambient temperature

With chromium(VI) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; trichlorosilane; water; tin(IV) chloride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; acetone; benzene;

DOI:10.1002/bscb.19860950906

Reference yield:

methyl 3-oxo-7,11-dimethyl-dodeca-6,10-dienoate (56523-17-2) → (1R,4aS,8aS)-(-)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene (108944-91-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 32.1 percent / SnCl₄, H₂O / CH₂Cl₂ / Ambient temperature

2: 96.1 percent / NaBH₄ / methanol / 5.5 h / -60 - -40 °C

3: 43.2 percent / 20 h / 80 - 90 °C

4: 60.3 percent / Et₃N, HSiCl₃ / benzene / 7 h / Heating

5: 87.4 percent / LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

6: 79.3 percent / pyridine / 18 h / 0 °C

7: 91.4 percent / CrO₃ / acetone / 0 degC, 10 min; r.t., 30 min

8: 96.8 percent / DBU / benzene / 12 h / Ambient temperature

With chromium(VI) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; trichlorosilane; water; tin(IV) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetone; benzene;

DOI:10.1002/bscb.19860950906

Reference yield:

(+/-)-8-oxo-12-nordriman-11-acid methyl ester (59684-77-4,65794-68-5,115304-46-6,131831-72-6,133102-26-8,49749-46-4,141317-75-1) → (1R,4aS,8aS)-(-)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene (108944-91-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 96.1 percent / NaBH₄ / methanol / 5.5 h / -60 - -40 °C

2: 43.2 percent / 20 h / 80 - 90 °C

3: 60.3 percent / Et₃N, HSiCl₃ / benzene / 7 h / Heating

4: 87.4 percent / LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

5: 79.3 percent / pyridine / 18 h / 0 °C

6: 91.4 percent / CrO₃ / acetone / 0 degC, 10 min; r.t., 30 min

7: 96.8 percent / DBU / benzene / 12 h / Ambient temperature

With chromium(VI) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; trichlorosilane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; pyridine; methanol; acetone; benzene;

DOI:10.1002/bscb.19860950906

upstream raw materials:

1-bromo-2,5-dimethoxybenzene

(4aS,8aS)-3,4,4aα,5,6,7,8,8aβ-octahydro-5,5,8aβ-trimethyl-1-methylidene-2(1H)-naphthalenone

trans geranyl acetone

methyl 3-oxo-7,11-dimethyl-dodeca-6,10-dienoate

Downstream raw materials:

(+)-zonarone

(-)-ent-zonarol

(-)-zonarol dimethyl ether