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

Base Information

• Chemical Name: 9-methoxy-6β-(3',4'-dimethoxyphenyl)-2β,5α-dimethyltricyclo<5.4.0.0^1,5>undec-9-en-8,11-dione
• CAS No.: 141582-07-2
• Molecular Formula: C₂₂H₂₆O₅
• Molecular Weight: 370.445

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

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

Chemical Property:

Purity/Quality:

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

There total 1 articles about 9-methoxy-6β-(3',4'-dimethoxyphenyl)-2β,5α-dimethyltricyclo<5.4.0.0^1,5>undec-9-en-8,11-dione 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: 66.0%

2-[(Z)-5-(3,4-Dimethoxy-phenyl)-1,4-dimethyl-pent-4-enyl]-4,5-dimethoxy-phenol (137438-68-7) → 9-methoxy-6β-(3',4'-dimethoxyphenyl)-2β,5α-dimethyltricyclo<5.4.0.01,5>undec-9-en-8,11-dione (141582-07-2)

Guidance literature:

With tetrabutylammonium tetrafluoroborate; In acetic anhydride; electrochemical oxidation;

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) → (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 (141582-11-8)

Guidance literature:

Multi-step reaction with 7 steps

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

2: 50 percent / NaBH₄ / dioxane; methanol / 0.83 h / 0 - 20 °C

3: 75 percent / CSA / acetone / 11 h / Ambient temperature

4: 73 percent / PCC-Celite / CH₂Cl₂ / 2 h / 0 °C

5: 97 percent / 2 M aq. HCl / dioxane / 5.5 h / Ambient temperature

6: 85 percent / H₂ / Pd/C / methanol / 13 h / Ambient temperature

7: 77 percent / p-TsOH / toluene / 3 h / Heating

With hydrogenchloride; sodium tetrahydroborate; pyridinium chlorochromate on silica gel; camphor-10-sulfonic acid; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; acetone; toluene;

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) → (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 (141599-30-6)

Guidance literature:

Multi-step reaction with 6 steps

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

2: 50 percent / NaBH₄ / dioxane; methanol / 0.83 h / 0 - 20 °C

3: 75 percent / CSA / acetone / 11 h / Ambient temperature

4: 73 percent / PCC-Celite / CH₂Cl₂ / 2 h / 0 °C

5: 97 percent / 2 M aq. HCl / dioxane / 5.5 h / Ambient temperature

6: 85 percent / H₂ / Pd/C / methanol / 13 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; pyridinium chlorochromate on silica gel; camphor-10-sulfonic acid; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; acetone;

DOI:10.1246/cl.1992.651

upstream raw materials:

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

Downstream raw materials:

(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

(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

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