(1S,4aR,8aR)-(+)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene

Base Information

• Chemical Name: (1S,4aR,8aR)-(+)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene
• CAS No.: 108944-90-7
• Molecular Formula: C₂₂H₃₂O₃
• Molecular Weight: 344.494
• Mol file: 108944-90-7.mol

Synonyms:(1S,4aR,8aR)-(+)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene

Chemical Property of (1S,4aR,8aR)-(+)-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 (1S,4aR,8aR)-(+)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene

There total 25 articles about (1S,4aR,8aR)-(+)-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: 95.0%

(-)-(4aR,8aR)-1-(2,5-dimethoxyphenyl)methyl-2-acetoxy-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene (211053-83-7) → (1S,4aR,8aR)-(+)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene (108944-90-7)

Guidance literature:

With potassium hydroxide; In methanol; for 6h; Ambient temperature;

DOI:10.1016/S0957-4166(98)00172-4

Reference yield:

rac-12-nor-drimane-8α,11-diol (59633-91-9,65754-93-0,108944-87-2,108944-88-3,136982-34-8,146611-16-7,807360-95-8) → (1S,4aR,8aR)-(+)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene (108944-90-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 99 percent / conc. H₂SO₄ / dimethylsulfoxide / 1 h / Ambient temperature

2: 99 percent / p-dimethylaminopyridine, pyridine / 1 h / Ambient temperature

3: acylase I (Aspergillus melleus) / diisopropyl ether; H₂O / 48 h / 33 °C

4: 92 percent / H₂ / 20percent Pd(OH)2-C / methanol / Ambient temperature

5: conc. H₂SO₄ / dimethylsulfoxide / 0.5 h / Ambient temperature

6: LiAlH₄, AlCl₃ / diethyl ether / 0.5 h / -20 °C

7: CBr₄, Ph₃P / tetrahydrofuran / 0.25 h / Ambient temperature

8: H₂ / 20percent Pd(OH)2-C / ethyl acetate / Ambient temperature

9: 97 percent / CrO₃, H₂SO₄ / acetone / 0 °C

10: 86 percent / 1,8-diazabicyclo<5,4>undec-7-ene / benzene / 0.5 h / Ambient temperature

11: 1.) CuI / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 1 h

12: tetrahydrofuran / 0.33 h / Ambient temperature

13: 95 percent / KOH / methanol / 6 h / Ambient temperature

With pyridine; chromium(VI) oxide; dmap; potassium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; aluminium trichloride; carbon tetrabromide; acylase I (Aspergillus melleus); sulfuric acid; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; di-isopropyl ether; water; dimethyl sulfoxide; ethyl acetate; acetone; benzene;

DOI:10.1016/S0957-4166(98)00172-4

Reference yield:

(1R,2S,4aR,8aR)-2-hydroxy-decahydro-5,5,8a-trimethyl-1-naphthylmethanol (190451-39-9,807360-95-8) → (1S,4aR,8aR)-(+)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene (108944-90-7)

Guidance literature:

Multi-step reaction with 9 steps

1: conc. H₂SO₄ / dimethylsulfoxide / 0.5 h / Ambient temperature

2: LiAlH₄, AlCl₃ / diethyl ether / 0.5 h / -20 °C

3: CBr₄, Ph₃P / tetrahydrofuran / 0.25 h / Ambient temperature

4: H₂ / 20percent Pd(OH)2-C / ethyl acetate / Ambient temperature

5: 97 percent / CrO₃, H₂SO₄ / acetone / 0 °C

6: 86 percent / 1,8-diazabicyclo<5,4>undec-7-ene / benzene / 0.5 h / Ambient temperature

7: 1.) CuI / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 1 h

8: tetrahydrofuran / 0.33 h / Ambient temperature

9: 95 percent / KOH / methanol / 6 h / Ambient temperature

With chromium(VI) oxide; potassium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; aluminium trichloride; carbon tetrabromide; sulfuric acid; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; dimethyl sulfoxide; ethyl acetate; acetone; benzene;

DOI:10.1016/S0957-4166(98)00172-4

upstream raw materials:

(4aR,8aR)-(+)-1-methylene-2-oxo-5,5,8a-trimethyldecahydronaphthalene

1-bromo-2,5-dimethoxybenzene

(-)-(4aR,8aR)-1-(2,5-dimethoxyphenyl)methyl-2-acetoxy-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene

rac-12-nor-drimane-8α,11-diol

Downstream raw materials:

(+)-zonarone

(+)-zonarol

(+)-zonarol dimethyl ether