Azulene, 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, (1S,4S,7R)-

Base Information

• Chemical Name: Azulene, 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, (1S,4S,7R)-
• CAS No.: 3691-12-1
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• Nikkaji Number: J20.860D
• Wikidata: Q67879675
• Mol file: 3691-12-1.mol

Synonyms:alpha-Guajene;7-Isopropenyl-1,4-dimethyl-1,2,3,4,5,6,7,8-octahydroazulene;Azulene, 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, (1S,4S,7R)-;ABQ2CB7VAC;a-Guaiene;UNII-ABQ2CB7VAC;ADIDQIZBYUABQK-UHFFFAOYSA-N;7-Isopropenyl-1,4-dimethyl-1,2,3,4,5,6,7,8-octahydroazulene-, [1S-(1.alpha.,4.alpha.,7.alpha.)]-;FT-0699683;Q67879675

Chemical Property of Azulene, 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, (1S,4S,7R)-

Chemical Property:

• Vapor Pressure: 0.0062mmHg at 25°C
• Boiling Point: 281.1°Cat760mmHg
• Flash Point: 111.2°C
• PSA: 0.00000
• Density: 0.89g/cm³
• LogP: 4.72520
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Dioxane (Sparingly, Sonicated), Methanol (Slightly)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 295

Purity/Quality:

99%, ^*data from raw suppliers

α-Guaiene(>85%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(CC2=C1CCC2C)C(=C)C
• Uses: α-Guaiene is a sesquiterpene and an essential oil component, shown to have antimicrobial activity.

Technology Process of Azulene, 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, (1S,4S,7R)-

There total 7 articles about Azulene, 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, (1S,4S,7R)- 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:

guaiol (489-86-1) → (1S,4S,7R)-7-Isopropenyl-1,4-dimethyl-1,2,3,4,5,6,7,8-octahydro-azulene (3691-12-1,53863-54-0)

Guidance literature:

With pyridine; thionyl chloride;

DOI:10.1016/S0040-4020(01)92224-0 DOI:10.1016/S0040-4039(01)99241-X

Reference yield:

2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]-propan-2-yl benzoate (13744-53-1) → (1S,4S,7R)-7-Isopropenyl-1,4-dimethyl-1,2,3,4,5,6,7,8-octahydro-azulene (3691-12-1,53863-54-0)

Guidance literature:

at 230 ℃; under 110 Torr;

DOI:10.1016/0040-4020(67)85074-9

Reference yield:

→ (1S,4S,7R)-7-Isopropenyl-1,4-dimethyl-1,2,3,4,5,6,7,8-octahydro-azulene (3691-12-1,53863-54-0)

Guidance literature:

DOI:10.1021/ja00866a051

upstream raw materials:

guaiol

2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]-propan-2-yl benzoate

2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]-propan-2-yl acetate

2-(3,8-dimethyl-1,2,3,3a,4,5,6,7-octahydro-5-azulenyl)-2-propanol

Downstream raw materials:

(3S,5R,8S)-3,8-dimethyl-5-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-azulen-1-one

(-)-α-Isopropyl-γ-acetobuttersaeure-methylester

caryophyllene oxide

Caryophyllene oxide

Refernces

• 1、 Huang, An-Cheng,Sumby, Christopher J.,Tiekink, Edward R.T.,Taylor, Dennis K.. "Synthesis of guaia-4(5)-en-11-ol, guaia-5(6)-en-11-ol, aciphyllene, 1- epi -melicodenones C and E, and other guaiane-type sesquiterpenoids via the diastereoselective epoxidation of guaiol". . p. 2522 - 2536. Retrieved 2015/01/09.
• 2、 Faraldos, Juan A.,Wu, Shuiqin,Chappell, Joe,Coates, Robert M.. "Doubly deuterium-labeled patchouli alcohol from cyclization of singly labeled [2-2H 1]farnesyl diphosphate catalyzed by recombinant patchoulol synthase". experimental part. p. 2998 - 3008. Retrieved 2010/05/01.