(1R,3aR,4S,4aR,5R,8R)-4-(3,4-Dimethoxy-phenyl)-5,8-dihydroxy-1,3a-dimethyl-octahydro-cyclopenta[1,4]cyclobuta[1,2]benzen-6-one

Base Information

• Chemical Name: (1R,3aR,4S,4aR,5R,8R)-4-(3,4-Dimethoxy-phenyl)-5,8-dihydroxy-1,3a-dimethyl-octahydro-cyclopenta[1,4]cyclobuta[1,2]benzen-6-one
• CAS No.: 141582-08-3
• Molecular Formula: C₂₁H₂₈O₅
• Molecular Weight: 360.45
• Mol file: 141582-08-3.mol

Synonyms:(1R,3aR,4S,4aR,5R,8R)-4-(3,4-Dimethoxy-phenyl)-5,8-dihydroxy-1,3a-dimethyl-octahydro-cyclopenta[1,4]cyclobuta[1,2]benzen-6-one

Chemical Property of (1R,3aR,4S,4aR,5R,8R)-4-(3,4-Dimethoxy-phenyl)-5,8-dihydroxy-1,3a-dimethyl-octahydro-cyclopenta[1,4]cyclobuta[1,2]benzen-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3aR,4S,4aR,5R,8R)-4-(3,4-Dimethoxy-phenyl)-5,8-dihydroxy-1,3a-dimethyl-octahydro-cyclopenta[1,4]cyclobuta[1,2]benzen-6-one

There total 2 articles about (1R,3aR,4S,4aR,5R,8R)-4-(3,4-Dimethoxy-phenyl)-5,8-dihydroxy-1,3a-dimethyl-octahydro-cyclopenta[1,4]cyclobuta[1,2]benzen-6-one 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:

2-[(Z)-5-(3,4-Dimethoxy-phenyl)-1,4-dimethyl-pent-4-enyl]-4,5-dimethoxy-phenol (137438-68-7) → (1R,3aR,4S,4aR,5R,8R)-4-(3,4-Dimethoxy-phenyl)-5,8-dihydroxy-1,3a-dimethyl-octahydro-cyclopenta[1,4]cyclobuta[1,2]benzen-6-one (141582-08-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / nBu₄NBF₄ / acetic anhydride / electrochemical oxidation

2: 1.) DIBAL-H, 2.) 2 M aq. HCl / 1.) toluene, from -78 deg C to RT, 65 min

With hydrogenchloride; tetrabutylammonium tetrafluoroborate; diisobutylaluminium hydride; In acetic anhydride;

DOI:10.1246/cl.1992.651

Reference yield:

9-methoxy-6β-(3',4'-dimethoxyphenyl)-2β,5α-dimethyltricyclo<5.4.0.01,5>undec-9-en-8,11-dione (141582-07-2) → (1R,3aR,4S,4aR,5R,8R)-4-(3,4-Dimethoxy-phenyl)-5,8-dihydroxy-1,3a-dimethyl-octahydro-cyclopenta[1,4]cyclobuta[1,2]benzen-6-one (141582-08-3)

Guidance literature:

With hydrogenchloride; diisobutylaluminium hydride; Yield given. Multistep reaction; 1.) toluene, from -78 deg C to RT, 65 min;

DOI:10.1246/cl.1992.651

Reference yield: 50.0%

(1R,3aR,4S,4aR,5R,8R)-4-(3,4-Dimethoxy-phenyl)-5,8-dihydroxy-1,3a-dimethyl-octahydro-cyclopenta[1,4]cyclobuta[1,2]benzen-6-one (141582-08-3) → (1R,3aR,4S,4aR,5R,8R)-4-(3,4-Dimethoxy-phenyl)-1,3a-dimethyl-decahydro-cyclopenta[1,4]cyclobuta[1,2]benzene-5,6,8-triol

Guidance literature:

With sodium tetrahydroborate; In 1,4-dioxane; methanol; at 0 - 20 ℃; for 0.833333h;

DOI:10.1246/cl.1992.651

upstream raw materials:

9-methoxy-6β-(3',4'-dimethoxyphenyl)-2β,5α-dimethyltricyclo<5.4.0.0^1,5>undec-9-en-8,11-dione

2-[(Z)-5-(3,4-Dimethoxy-phenyl)-1,4-dimethyl-pent-4-enyl]-4,5-dimethoxy-phenol

Downstream raw materials:

(3aS,5aS,8S,8aS)-5-(3,4-Dimethoxy-phenyl)-5a,8-dimethyl-3,3a,5a,6,7,8-hexahydro-2H-cyclopenta[c]pentalen-1-one

(1S,3aS,4R,4aS,5R,8aS)-4-(3,4-Dimethoxy-phenyl)-5-hydroxy-1,3a-dimethyl-octahydro-cyclopenta[1,4]cyclobuta[1,2]benzen-8-one

C₂₄H₃₄O₅

C₂₄H₃₂O₅