(+)-9-hydroxy-4-(4-hydroxyphenyl)-9-methyl-6-(thiophen-2-yl)-11-(propan-2-yl)tricyclo-[5.2.2.0^2,6]undeca-4,10-diene-3,8-dione

Base Information

• Chemical Name: (+)-9-hydroxy-4-(4-hydroxyphenyl)-9-methyl-6-(thiophen-2-yl)-11-(propan-2-yl)tricyclo-[5.2.2.0^2,6]undeca-4,10-diene-3,8-dione
• CAS No.: 1414335-79-7
• Molecular Formula: C₂₅H₂₄O₄S
• Molecular Weight: 420.529

Synonyms:(+)-9-hydroxy-4-(4-hydroxyphenyl)-9-methyl-6-(thiophen-2-yl)-11-(propan-2-yl)tricyclo-[5.2.2.0^2,6]undeca-4,10-diene-3,8-dione

Chemical Property of (+)-9-hydroxy-4-(4-hydroxyphenyl)-9-methyl-6-(thiophen-2-yl)-11-(propan-2-yl)tricyclo-[5.2.2.0^2,6]undeca-4,10-diene-3,8-dione

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Technology Process of (+)-9-hydroxy-4-(4-hydroxyphenyl)-9-methyl-6-(thiophen-2-yl)-11-(propan-2-yl)tricyclo-[5.2.2.0^2,6]undeca-4,10-diene-3,8-dione

There total 4 articles about (+)-9-hydroxy-4-(4-hydroxyphenyl)-9-methyl-6-(thiophen-2-yl)-11-(propan-2-yl)tricyclo-[5.2.2.0^2,6]undeca-4,10-diene-3,8-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: 67.0%

(+)-4-(4-methoxyphenyl)-9-hydroxy-9-methyl-6-(thiophen-2-yl)-11-(propan-2-yl)tricyclo[5.2.2.02,6]undeca-4,10-diene-3,8-dione (1414335-75-3) → (+)-9-hydroxy-4-(4-hydroxyphenyl)-9-methyl-6-(thiophen-2-yl)-11-(propan-2-yl)tricyclo-[5.2.2.02,6]undeca-4,10-diene-3,8-dione (1414335-79-7)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ja3084708

Reference yield:

ethyl p-methoxyphenylacetate (14062-18-1) → (+)-9-hydroxy-4-(4-hydroxyphenyl)-9-methyl-6-(thiophen-2-yl)-11-(propan-2-yl)tricyclo-[5.2.2.02,6]undeca-4,10-diene-3,8-dione (1414335-79-7)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium hexamethyldisilazane / tetrahydrofuran / -10 - 20 °C

2: sodium hydroxide; water / methanol; tetrahydrofuran / 55 °C

3: phosgene; aluminum (III) chloride / dichloromethane / 20 °C

4: palladium diacetate; XPhos; potassium carbonate / toluene; water

5: 10% rhodium on carbon / 1,3,5-trimethyl-benzene / 18 h / 150 °C / Inert atmosphere

6: boron tribromide / dichloromethane / 4 h / -78 - 20 °C / Inert atmosphere

With phosgene; aluminum (III) chloride; 10% rhodium on carbon; water; palladium diacetate; sodium hexamethyldisilazane; boron tribromide; potassium carbonate; sodium hydroxide; XPhos; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1,3,5-trimethyl-benzene; 5: |Diels-Alder Cycloaddition;

DOI:10.1021/ja3084708

Reference yield:

C14H17ClO3 → (+)-9-hydroxy-4-(4-hydroxyphenyl)-9-methyl-6-(thiophen-2-yl)-11-(propan-2-yl)tricyclo-[5.2.2.02,6]undeca-4,10-diene-3,8-dione (1414335-79-7)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydroxide; water / methanol; tetrahydrofuran / 55 °C

2: phosgene; aluminum (III) chloride / dichloromethane / 20 °C

3: palladium diacetate; XPhos; potassium carbonate / toluene; water

4: 10% rhodium on carbon / 1,3,5-trimethyl-benzene / 18 h / 150 °C / Inert atmosphere

5: boron tribromide / dichloromethane / 4 h / -78 - 20 °C / Inert atmosphere

With phosgene; aluminum (III) chloride; 10% rhodium on carbon; water; palladium diacetate; boron tribromide; potassium carbonate; sodium hydroxide; XPhos; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1,3,5-trimethyl-benzene; 4: |Diels-Alder Cycloaddition;

DOI:10.1021/ja3084708

upstream raw materials:

5-(4-methoxyphenyl)-3-(thiophen-2-yl)cyclopent-2-en-1-one

(+)-4-(4-methoxyphenyl)-9-hydroxy-9-methyl-6-(thiophen-2-yl)-11-(propan-2-yl)tricyclo[5.2.2.0^2,6]undeca-4,10-diene-3,8-dione

ethyl p-methoxyphenylacetate

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