α-curcumene

Base Information

• Chemical Name: α-curcumene
• CAS No.: 644-30-4
• Molecular Formula: C15H22
• Molecular Weight: 202.34
• European Community (EC) Number: 866-579-4
• UNII: S24T013WOF
• DSSTox Substance ID: DTXSID90862351
• Nikkaji Number: J12.501F
• Wikidata: Q27132148
• ChEMBL ID: CHEMBL4210821
• Mol file: 644-30-4.mol

Synonyms:2-Heptene,2-methyl-6-p-tolyl- (7CI,8CI); Benzene, 1-(1,5-dimethyl-4-hexenyl)-4-methyl-(9CI); a-Curcumene (6CI); (?à)-a-Curcumene;1-(1,5-Dimethyl-4-hexenyl)-4-methylbenzene; Curcumene; ar-Curcumene

Chemical Property of α-curcumene

Chemical Property:

• Vapor Pressure: 0.00814mmHg at 25°C
• Refractive Index: 1.4989
• Boiling Point: 276.3°C at 760 mmHg
• Flash Point: 117.2°C
• PSA: 0.00000
• Density: 0.873g/cm³
• LogP: 4.84490
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 202.172150702
• Heavy Atom Count: 15
• Complexity: 190

Purity/Quality:

Analysis control,GC≥90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(C)CCC=C(C)C

Technology Process of α-curcumene

There total 187 articles about α-curcumene 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: 97.0%

C15H19F3O3S + methylmagnesium bromide (75-16-1) → (S)-curcumene (3649-81-8,4176-17-4,644-30-4,4176-06-1)

Guidance literature:

With iron(III)-acetylacetonate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; at 0 ℃; for 0.25h;

DOI:10.1021/ja1034842

Reference yield: 90.0%

6-Methyl-hept-5-en-2-on (110-93-0,129085-68-3) + para-bromotoluene (106-38-7) → ar-curcumene (644-30-4)

Guidance literature:

With ammonia; lithium; In diethyl ether;

Reference yield: 89.0%

(S)-5-methyl-2-(6-methylhept-5-en-2-yl)benzoic acid (1580457-76-6) → (S)-curcumene (3649-81-8,4176-17-4,644-30-4,4176-06-1)

Guidance literature:

With quinoline; copper; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c4ob00018h

upstream raw materials:

(-)-β-curcumene

2-(3-Methyl-but-2-enyl)-2-((S)-1-p-tolyl-ethyl)-[1,3]dithiane

diethoxyphosphoryl-acetic acid ethyl ester

isopropyltriphenylphosphonium iodide

Downstream raw materials:

(+/-)-2-methyl-6-(4'-methylphenyl)-1-hepten-3-ol

(+)-(7S,9S)-dihydro-ar-turmerol

(+)-(7S,9R)-dihydro-ar-turmerol

(+)-(S)-dihydro-ar-curcumene

Refernces

• 1、 Skotnitzki, Juri,Kremsmair, Alexander,Keefer, Daniel,Gong, Ye,de Vivie-Riedle, Regina,Knochel, Paul. "Stereoselective Csp3?Csp2 Cross-Couplings of Chiral Secondary Alkylzinc Reagents with Alkenyl and Aryl Halides". . p. 320 - 324. Retrieved 2019/11/26.
• 2、 -. "A asymmetric catalytic synthesis (S)- aryl curcumene method". Paragraph 0011; 0043; 0044; 0045. . Retrieved 2017/08/25.