(-)-(4aR,4bR,7aS,7bR)-4,4a,4b,5,6,7,7a,7b-octahydro-2-methoxy-7a-(4-methoxyphenyl)-1H-benzo<3,4>-cyclobuta<1,2>cyclopentan-1,4-dione

Base Information

• Chemical Name: (-)-(4aR,4bR,7aS,7bR)-4,4a,4b,5,6,7,7a,7b-octahydro-2-methoxy-7a-(4-methoxyphenyl)-1H-benzo<3,4>-cyclobuta<1,2>cyclopentan-1,4-dione
• CAS No.: 224446-59-7
• Molecular Formula: C₁₉H₂₀O₄
• Molecular Weight: 312.365

Synonyms:(-)-(4aR,4bR,7aS,7bR)-4,4a,4b,5,6,7,7a,7b-octahydro-2-methoxy-7a-(4-methoxyphenyl)-1H-benzo<3,4>-cyclobuta<1,2>cyclopentan-1,4-dione

Chemical Property of (-)-(4aR,4bR,7aS,7bR)-4,4a,4b,5,6,7,7a,7b-octahydro-2-methoxy-7a-(4-methoxyphenyl)-1H-benzo<3,4>-cyclobuta<1,2>cyclopentan-1,4-dione

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Technology Process of (-)-(4aR,4bR,7aS,7bR)-4,4a,4b,5,6,7,7a,7b-octahydro-2-methoxy-7a-(4-methoxyphenyl)-1H-benzo<3,4>-cyclobuta<1,2>cyclopentan-1,4-dione

There total 2 articles about (-)-(4aR,4bR,7aS,7bR)-4,4a,4b,5,6,7,7a,7b-octahydro-2-methoxy-7a-(4-methoxyphenyl)-1H-benzo<3,4>-cyclobuta<1,2>cyclopentan-1,4-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:

1-(p-methoxyphenyl)-1-cyclopentene (709-12-6) + 2-methoxy-1,4-benzoquinone (2880-58-2) → rel-(3aR,8bR)-2,3,3a,8b-tetrahydro-6-methoxy-3a-(4-methoxyphenyl)-1H-cyclopentabenzofuran-7-ol + (-)-(4aR,4bR,7aS,7bR)-4,4a,4b,5,6,7,7a,7b-octahydro-2-methoxy-7a-(4-methoxyphenyl)-1H-benzo<3,4>-cyclobuta<1,2>cyclopentan-1,4-dione (224446-59-7)

Guidance literature:

With titanium(IV) isopropylate; (+)-C₃₆H₃₂O₄; titanium tetrachloride; Yield given; Multistep reaction. Yields of byproduct given; 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 deg C, 20 min;

DOI:10.1021/jo982164s

Reference yield:

1-(p-methoxyphenyl)-1-cyclopentene (709-12-6) + 2-methoxy-1,4-benzoquinone (2880-58-2) → rel-(3aR,8bR)-2,3,3a,8b-tetrahydro-6-methoxy-3a-(4-methoxyphenyl)-1H-cyclopentabenzofuran-7-ol + (+)-(4aS,4bS,7aR,7bS)-4,4a,4b,5,6,7,7a,7b-octahydro-2-methoxy-7a-(4-methoxyphenyl)-1H-benzo<3,4>-cyclobuta<1,2>cyclopentan-1,4-dione + (-)-(4aR,4bR,7aS,7bR)-4,4a,4b,5,6,7,7a,7b-octahydro-2-methoxy-7a-(4-methoxyphenyl)-1H-benzo<3,4>-cyclobuta<1,2>cyclopentan-1,4-dione (224446-59-7)

Guidance literature:

With titanium(IV) isopropylate; (-)-C₃₆H₃₂O₄; titanium tetrachloride; Yield given; Multistep reaction. Yields of byproduct given; 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 deg C, 20 min;

DOI:10.1021/jo982164s

Reference yield: 94.0%

(-)-(4aR,4bR,7aS,7bR)-4,4a,4b,5,6,7,7a,7b-octahydro-2-methoxy-7a-(4-methoxyphenyl)-1H-benzo<3,4>-cyclobuta<1,2>cyclopentan-1,4-dione (224446-59-7) → (+)-(3aR,8bR)-2,3,3a,8b-tetrahydro-6-methoxy-3a-(4-methoxyphenyl)-1H-cyclopentabenzofuran-7-ol (224446-60-0)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 0.0833333h; Ambient temperature;

DOI:10.1021/jo982164s

upstream raw materials:

1-(p-methoxyphenyl)-1-cyclopentene

2-methoxy-1,4-benzoquinone

Downstream raw materials:

(+)-(3aR,8bR)-2,3,3a,8b-tetrahydro-6-methoxy-3a-(4-methoxyphenyl)-1H-cyclopentabenzofuran-7-ol

(3aR,3bR,7S,7aR,7bS)-7-hydroxy-6-methoxy-7b-(4-methoxyphenyl)-1,2,3,3a,3b,7,7a,7b-octahydrocyclopenta<3,4>cyclobuta<1,2>benzen-4-one

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