2-isopropyl-5-methyl-5-(5-methylfuran-2-yl)cyclohex-2-ene-1,4-dione

Base Information

• Chemical Name: 2-isopropyl-5-methyl-5-(5-methylfuran-2-yl)cyclohex-2-ene-1,4-dione
• CAS No.: 1262865-08-6
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.306
• Mol file: 1262865-08-6.mol

Synonyms:2-isopropyl-5-methyl-5-(5-methylfuran-2-yl)cyclohex-2-ene-1,4-dione

Chemical Property of 2-isopropyl-5-methyl-5-(5-methylfuran-2-yl)cyclohex-2-ene-1,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-isopropyl-5-methyl-5-(5-methylfuran-2-yl)cyclohex-2-ene-1,4-dione

There total 7 articles about 2-isopropyl-5-methyl-5-(5-methylfuran-2-yl)cyclohex-2-ene-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: 46.0%

2-methylfuran (534-22-5) + (5-isopropyl-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)boronic acid (1262864-87-8) → 2-isopropyl-5-methyl-5-(5-methylfuran-2-yl)cyclohex-2-ene-1,4-dione (1262865-08-6) + 5-isopropyl-2-methyl-3-(5-methylfuran-2-yl)cyclohexa-2,5-diene-1,4-dione (1262865-09-7)

Guidance literature:

With iron(III) chloride hexahydrate; In dichloromethane; at 25 ℃; for 2h; regioselective reaction;

DOI:10.1021/ol1028964

Reference yield:

(3-isopropyl-2,5-dimethoxy-6-methylphenyl)boronic acid (1262865-14-4) → 2-isopropyl-5-methyl-5-(5-methylfuran-2-yl)cyclohex-2-ene-1,4-dione (1262865-08-6) + 5-isopropyl-2-methyl-3-(5-methylfuran-2-yl)cyclohexa-2,5-diene-1,4-dione (1262865-09-7)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium cerium (IV) nitrate; water / acetonitrile / 0.5 h / 0 °C

2: iron(III) chloride hexahydrate / dichloromethane / 2 h / 25 °C

With ammonium cerium (IV) nitrate; iron(III) chloride hexahydrate; water; In dichloromethane; acetonitrile; 2: Friedel Crafts alkylation;

DOI:10.1021/ol1028964

Reference yield:

thymol (89-83-8) → 2-isopropyl-5-methyl-5-(5-methylfuran-2-yl)cyclohex-2-ene-1,4-dione (1262865-08-6) + 5-isopropyl-2-methyl-3-(5-methylfuran-2-yl)cyclohexa-2,5-diene-1,4-dione (1262865-09-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: bromine; acetic acid / 0 °C

2.1: water; periodic acid / acetonitrile / 70 - 80 °C

3.1: sodium dithionite; water / diethyl ether / 0.5 h / 25 °C

4.1: potassium carbonate / acetone / 4 h / Reflux

5.1: n-butyllithium / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

5.2: -78 - 25 °C / Inert atmosphere

5.3: 25 °C

6.1: ammonium cerium (IV) nitrate; water / acetonitrile / 0.5 h / 0 °C

7.1: iron(III) chloride hexahydrate / dichloromethane / 2 h / 25 °C

With n-butyllithium; sodium dithionite; ammonium cerium (IV) nitrate; iron(III) chloride hexahydrate; water; bromine; potassium carbonate; acetic acid; periodic acid; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; acetonitrile; 7.1: Friedel Crafts alkylation;

DOI:10.1021/ol1028964

upstream raw materials:

2-methylfuran

(5-isopropyl-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)boronic acid

(3-isopropyl-2,5-dimethoxy-6-methylphenyl)boronic acid

thymol