(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

Base Information

Chemical Name:(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
CAS No.:141599-30-6
Molecular Formula:C₂₁H₂₈O₄
Molecular Weight:344.451
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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: 85.0%

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

: 141599-30-6
(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

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; for 13h; Ambient temperature;
DOI:10.1246/cl.1992.651

Reference yield:

: 137438-68-7
2-[(Z)-5-(3,4-Dimethoxy-phenyl)-1,4-dimethyl-pent-4-enyl]-4,5-dimethoxy-phenol

: 141599-30-6
(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

Guidance literature:: Multi-step reaction with 7 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

3: 50 percent / NaBH₄ / dioxane; methanol / 0.83 h / 0 - 20 °C

4: 75 percent / CSA / acetone / 11 h / Ambient temperature

5: 73 percent / PCC-Celite / CH₂Cl₂ / 2 h / 0 °C

6: 97 percent / 2 M aq. HCl / dioxane / 5.5 h / Ambient temperature

7: 85 percent / H₂ / Pd/C / methanol / 13 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; pyridinium chlorochromate on silica gel; camphor-10-sulfonic acid; tetrabutylammonium tetrafluoroborate; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; acetic anhydride; acetone;
DOI:10.1246/cl.1992.651

Reference yield:

: 141582-08-3
(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

: 141599-30-6
(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

Guidance literature:: Multi-step reaction with 5 steps

1: 50 percent / NaBH₄ / dioxane; methanol / 0.83 h / 0 - 20 °C

2: 75 percent / CSA / acetone / 11 h / Ambient temperature

3: 73 percent / PCC-Celite / CH₂Cl₂ / 2 h / 0 °C

4: 97 percent / 2 M aq. HCl / dioxane / 5.5 h / Ambient temperature

5: 85 percent / H₂ / Pd/C / methanol / 13 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; pyridinium chlorochromate on silica gel; camphor-10-sulfonic acid; hydrogen; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; acetone;
DOI:10.1246/cl.1992.651