(5aR,9aR)-6,6,9a-trimethyl-4,5,5a,6,7,8,9,9a-octahydronaphtho[1,2-c]furan

Base Information

• Chemical Name: (5aR,9aR)-6,6,9a-trimethyl-4,5,5a,6,7,8,9,9a-octahydronaphtho[1,2-c]furan
• CAS No.: 79895-94-6
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.339
• Mol file: 79895-94-6.mol

Synonyms:Euryfuran;

Chemical Property of (5aR,9aR)-6,6,9a-trimethyl-4,5,5a,6,7,8,9,9a-octahydronaphtho[1,2-c]furan

Chemical Property:

• Vapor Pressure: 0.00746mmHg at 25°C
• Boiling Point: 277.9°C at 760 mmHg
• Flash Point: 114.3°C
• PSA: 13.14000
• Density: 0.973g/cm³
• LogP: 4.30980

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (5aR,9aR)-6,6,9a-trimethyl-4,5,5a,6,7,8,9,9a-octahydronaphtho[1,2-c]furan

There total 49 articles about (5aR,9aR)-6,6,9a-trimethyl-4,5,5a,6,7,8,9,9a-octahydronaphtho[1,2-c]furan 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: 40.0%

Dithiocarbonic acid S-methyl ester O-((5S,5aS,9aS)-6,6,9a-trimethyl-4,5,5a,6,7,8,9,9a-octahydro-naphtho[1,2-c]furan-5-yl) ester (137644-74-7) → (+/-)-euryfuran (50490-43-2,67919-45-3,69780-10-5,78853-99-3,79895-94-6,137695-43-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 90 ℃;

DOI:10.3987/COM-91-5794

Reference yield:

(4,4-Dimethyl-4,5,6,7-tetrahydro-isobenzofuran-1-yl)-methanol (137644-71-4) → (+/-)-euryfuran (50490-43-2,67919-45-3,69780-10-5,78853-99-3,79895-94-6,137695-43-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / benzene / 6 h / Ambient temperature

2: 88 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 83 °C

3: 26 percent / o-xylene / 3 h / 100 °C

4: 79 percent / lithium triethylhydroborate / tetrahydrofuran; hexane / 14 h / Ambient temperature

5: 98 percent / DMSO, triethylamine, sulfur trioxide pyridine complex / CH₂Cl₂ / 2 h / 0 °C

6: 63 percent / tris(triphenylphosphine)rhodium(I) chloride / benzene / 1 h / Heating

7: hydrogen / 10percent palladium on carbon / ethyl acetate / 10 h / Ambient temperature

With sodium hydroxide; Wilkinson's catalyst; potassium tert-butylate; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; sulfur trioxide pyridine complex; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; o-xylene; ethyl acetate; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(01)85635-0

Reference yield:

2-propynyl (4,5,6,7-tetrahydro-4,4-dimethyl-isobenzofuran-1-yl)methyl ether (137644-77-0) → (+/-)-euryfuran (50490-43-2,67919-45-3,69780-10-5,78853-99-3,79895-94-6,137695-43-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 83 °C

2: 26 percent / o-xylene / 3 h / 100 °C

3: 79 percent / lithium triethylhydroborate / tetrahydrofuran; hexane / 14 h / Ambient temperature

4: 98 percent / DMSO, triethylamine, sulfur trioxide pyridine complex / CH₂Cl₂ / 2 h / 0 °C

5: 63 percent / tris(triphenylphosphine)rhodium(I) chloride / benzene / 1 h / Heating

6: hydrogen / 10percent palladium on carbon / ethyl acetate / 10 h / Ambient temperature

With Wilkinson's catalyst; potassium tert-butylate; hydrogen; sulfur trioxide pyridine complex; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; o-xylene; ethyl acetate; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(01)85635-0

upstream raw materials:

(5aR,9aR)-3-Butylsulfanyl-6,6,9a-trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan

4,6,7,8,9,9a-hexahydro-6,6,9a-trimethylnaphtho<1,2-c>-furan

Dithiocarbonic acid S-methyl ester O-((5S,5aS,9aS)-6,6,9a-trimethyl-4,5,5a,6,7,8,9,9a-octahydro-naphtho[1,2-c]furan-5-yl) ester

4,5,6,7-tetrahydroisobenzofuran-5-one

Downstream raw materials:

(+/-)-confertifolin

(5aR,9aR)-1-Hydroxy-6,6,9a-trimethyl-4,5,5a,6,7,8,9,9a-octahydro-1H-naphtho[1,2-c]furan-3-one