alpha,beta-Thujone

Base Information

• Chemical Name: alpha,beta-Thujone
• CAS No.: 76231-76-0
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• Hs Code.: 2914299000
• European Community (EC) Number: 629-556-8
• DSSTox Substance ID: DTXSID3040774
• Wikipedia: Thujone
• Metabolomics Workbench ID: 130974
• ChEMBL ID: CHEMBL3277899
• Mol file: 76231-76-0.mol

Synonyms:(+)-thujone;(-)-thujone;3-isothujone;3-thujanone;alpha, beta-thujone;alpha-thujone;beta-thujone;beta-thujone, (1alpha,4alpha,5alpha)-isomer;beta-thujone, (1S-(1alpha,4alpha,5alpha))-isomer;beta-thujone, 1S-(1alpha,4beta,5alpha)-isomer;cis-thujone;thujone

Chemical Property of alpha,beta-Thujone

Chemical Property:

• Vapor Pressure: 0.323mmHg at 25°C
• Refractive Index: n20/D 1.455(lit.)
• Boiling Point: 84-86 °C/17 mmHg(lit.)
• Flash Point: 64 °C
• PSA: 17.07000
• Density: 0.925 g/mL at 25 °C(lit.)
• LogP: 2.25760
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly), Methanol (Sl
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 207

Purity/Quality:

98%,99%, ^*data from raw suppliers

α,β-Thujone ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 23/24/25-36/37/38-42/43
• Safety Statements: 23-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CC2(CC1=O)C(C)C
• Isomeric SMILES: CC1[C@H]2C[C@]2(CC1=O)C(C)C
• Uses: α,β-Thujone is a component of the essential oil of Pistacia vera L. It is also used as as a reactant in organic synthesis.

Technology Process of alpha,beta-Thujone

There total 7 articles about alpha,beta-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:

(1R)-2c-Methyl-5c-isopropyl-(1rH)-bicyclo<3.1.0>hexan, (-)-Thujan B, (-)-cis-Thujan

α-Thujaketocarbonsaeuremethylester

α-Thujaoximinocarbonsaeuremethylester

(1R-(1α,2α/β,6α))-2-methyl-6-(1-methylethyl)bicyclo-[4.1.0]heptan-3-one