N-(6-hydroxy-tricyclo[6.2.2.0^2,7]dodeca-2⁽⁷⁾,3,5,9-tetraen-3-yl)-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-(6-hydroxy-tricyclo[6.2.2.0^2,7]dodeca-2⁽⁷⁾,3,5,9-tetraen-3-yl)-4-methyl-benzenesulfonamide
• CAS No.: 863582-15-4
• Molecular Formula: C₁₉H₁₉NO₃S
• Molecular Weight: 341.431

Synonyms:N-(6-hydroxy-tricyclo[6.2.2.0^2,7]dodeca-2⁽⁷⁾,3,5,9-tetraen-3-yl)-4-methyl-benzenesulfonamide

Chemical Property of N-(6-hydroxy-tricyclo[6.2.2.0^2,7]dodeca-2⁽⁷⁾,3,5,9-tetraen-3-yl)-4-methyl-benzenesulfonamide

Chemical Property:

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Technology Process of N-(6-hydroxy-tricyclo[6.2.2.0^2,7]dodeca-2⁽⁷⁾,3,5,9-tetraen-3-yl)-4-methyl-benzenesulfonamide

There total 3 articles about N-(6-hydroxy-tricyclo[6.2.2.0^2,7]dodeca-2⁽⁷⁾,3,5,9-tetraen-3-yl)-4-methyl-benzenesulfonamide 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:

4-methyl-N-(6-oxo-tricyclo[6.2.2.02,7]dodeca-2(7),4,9-trien-3-ylidene)-benzenesulfonamide → N-(6-hydroxy-tricyclo[6.2.2.02,7]dodeca-2(7),3,5,9-tetraen-3-yl)-4-methyl-benzenesulfonamide (863582-15-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1021/jo050706h

Reference yield:

4-methyl-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenesulfonamide (37051-70-0) → N-(6-hydroxy-tricyclo[6.2.2.02,7]dodeca-2(7),3,5,9-tetraen-3-yl)-4-methyl-benzenesulfonamide (863582-15-4)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 24 h / 20 °C

2: 1.45 g / DBU / CH₂Cl₂ / 0.17 h / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; 1: Diels-Alder reaction;

DOI:10.1021/jo050706h

Reference yield:

N-(4-hydroxyphenyl)-4-methylbenzenesulfonamide (1146-43-6) → N-(6-hydroxy-tricyclo[6.2.2.02,7]dodeca-2(7),3,5,9-tetraen-3-yl)-4-methyl-benzenesulfonamide (863582-15-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / NaIO₄ on silica gel / CH₂Cl₂ / 2 h / 20 °C

2: CH₂Cl₂ / 24 h / 20 °C

3: 1.45 g / DBU / CH₂Cl₂ / 0.17 h / 20 °C

With sodium periodate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; 2: Diels-Alder reaction;

DOI:10.1021/jo050706h

upstream raw materials:

4-methyl-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenesulfonamide

N-(4-hydroxyphenyl)-4-methylbenzenesulfonamide

Downstream raw materials:

acetic acid 6-(toluene-4-sulfonylamino)-tricyclo[6.2.2.0^2,7]dodeca-2⁽⁷⁾,3,5,9-tetraen-3-yl ester

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