1-[4-diazo-3-oxo-4-(2,4,6-trimethylphenylsulfonyl)butyl]-1-methyl-2,5-cyclohexadiene

Base Information

• Chemical Name: 1-[4-diazo-3-oxo-4-(2,4,6-trimethylphenylsulfonyl)butyl]-1-methyl-2,5-cyclohexadiene
• CAS No.: 510730-42-4
• Molecular Formula: C₂₀H₂₄N₂O₃S
• Molecular Weight: 372.488

Synonyms:1-[4-diazo-3-oxo-4-(2,4,6-trimethylphenylsulfonyl)butyl]-1-methyl-2,5-cyclohexadiene

Chemical Property of 1-[4-diazo-3-oxo-4-(2,4,6-trimethylphenylsulfonyl)butyl]-1-methyl-2,5-cyclohexadiene

Chemical Property:

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Technology Process of 1-[4-diazo-3-oxo-4-(2,4,6-trimethylphenylsulfonyl)butyl]-1-methyl-2,5-cyclohexadiene

There total 4 articles about 1-[4-diazo-3-oxo-4-(2,4,6-trimethylphenylsulfonyl)butyl]-1-methyl-2,5-cyclohexadiene 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%

1-methyl-1-[3-oxo-4-(2,4,6-trimethylphenylsulfonyl)butyl]-2,5-cyclohexadiene (510730-41-3) → 1-[4-diazo-3-oxo-4-(2,4,6-trimethylphenylsulfonyl)butyl]-1-methyl-2,5-cyclohexadiene (510730-42-4)

Guidance literature:

With 4-toluenesulfonyl azide; triethylamine; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1021/ja029534l

Reference yield:

ethyl 3-(1-methyl-2,5-cyclohexadienyl)propanate (510730-37-7) → 1-[4-diazo-3-oxo-4-(2,4,6-trimethylphenylsulfonyl)butyl]-1-methyl-2,5-cyclohexadiene (510730-42-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / nBuLi / tetrahydrofuran / 1 h / 0 °C

2: 85 percent / triethylamine; p-toluenesulfonyl azide / acetonitrile / 3 h / 20 °C

With n-butyllithium; 4-toluenesulfonyl azide; triethylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ja029534l

Reference yield:

ethyl (E)-3-(1-methyl-2,5-cyclohexadienyl)propenoate (510730-36-6) → 1-[4-diazo-3-oxo-4-(2,4,6-trimethylphenylsulfonyl)butyl]-1-methyl-2,5-cyclohexadiene (510730-42-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / NiCl₂*6H₂O; NaBH₄ / methanol / 1.5 h / 0 °C

2: 95 percent / nBuLi / tetrahydrofuran / 1 h / 0 °C

3: 85 percent / triethylamine; p-toluenesulfonyl azide / acetonitrile / 3 h / 20 °C

With sodium tetrahydroborate; n-butyllithium; 4-toluenesulfonyl azide; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/ja029534l

upstream raw materials:

1-methyl-1-[3-oxo-4-(2,4,6-trimethylphenylsulfonyl)butyl]-2,5-cyclohexadiene

ethyl (E)-3-(1-methyl-2,5-cyclohexadienyl)propenoate

ethyl 3-(1-methyl-2,5-cyclohexadienyl)propanate

1-methyl-2,5-cyclohexadiene-1-carboxaldehyde

Downstream raw materials:

(1R,5S,6S,7R)-1-methyl-8-oxo-7-(2,4,6-trimethylphenylsulfonyl)tricyclo[4.4.0.0^5,7]dec-2-ene

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