Thujone

Base Information

• Chemical Name: Thujone
• CAS No.: 116562-18-6
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• Mol file: 116562-18-6.mol

Synonyms:

Chemical Property of Thujone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thujone

There total 7 articles about Thujone 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: 75.0%

1-isopropylbicyclo[3.1.0]hexan-3-one + methyl iodide (74-88-4) → 4α-H-thujan-3-one (471-15-8,546-80-5,1125-12-8,58501-78-3,59573-80-7,69257-13-2,76231-76-0,78821-49-5,116562-18-6,116562-20-0)

Guidance literature:

1-isopropylbicyclo[3.1.0]hexan-3-one; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

methyl iodide; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; toluene; at -78 ℃; for 2h;

DOI:10.1039/c6cc05376a

Reference yield:

3-isopropylcyclopent-3-en-1-ol → 4α-H-thujan-3-one (471-15-8,546-80-5,1125-12-8,58501-78-3,59573-80-7,69257-13-2,76231-76-0,78821-49-5,116562-18-6,116562-20-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diethylzinc / hexane; dichloromethane / 0.17 h / 0 °C

1.2: 16 h / 0 - 20 °C

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 4 h / 20 °C

3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C

3.2: 2 h / -78 °C

With diethylzinc; potassium hexamethylsilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; toluene; 1.1: |Simmons-Smith Cyclopropanation / 1.2: |Simmons-Smith Cyclopropanation;

DOI:10.1039/c6cc05376a

Reference yield:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → 4α-H-thujan-3-one (471-15-8,546-80-5,1125-12-8,58501-78-3,59573-80-7,69257-13-2,76231-76-0,78821-49-5,116562-18-6,116562-20-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyrrolidine / methanol / 2 h / 0 - 20 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

2.2: 17 h / 0 - 20 °C

2.3: 24 h / 20 °C

3.1: diethylzinc / hexane; dichloromethane / 0.17 h / 0 °C

3.2: 16 h / 0 - 20 °C

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 4 h / 20 °C

5.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C

5.2: 2 h / -78 °C

With pyrrolidine; lithium aluminium tetrahydride; diethylzinc; potassium hexamethylsilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 3.1: |Simmons-Smith Cyclopropanation / 3.2: |Simmons-Smith Cyclopropanation;

DOI:10.1039/c6cc05376a

upstream raw materials:

cyclopenta-1,3-diene

methyl iodide

6,6'-dimethyl fulvene

Downstream raw materials:

Thujone-4β-carboxylic Acid

((1S)-2c-acetyl-1-isopropyl-cycloprop-r-yl)-acetic acid

4β-(Hydroxymethyl)-thujan-3-one

Refernces

• 1、 Rice,Wilson. "(-) 3 Isothujone, a small nonnitrogenous molecule with antinociceptive activity in mice". . p. 1054 - 1057. Retrieved 2007/10/13.