1,3,3-Trimethyl-2-oxabicyclo[2.2.2]oct-5-ene

Base Information

• Chemical Name: 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]oct-5-ene
• CAS No.: 92760-25-3
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• DSSTox Substance ID: DTXSID80335140
• Nikkaji Number: J441.994D
• Wikidata: Q67879829
• Metabolomics Workbench ID: 47184
• Mol file: 92760-25-3.mol

Synonyms:2,3-Dehydro-1,8-cineole;Dehydrocineole;1,3,3-Trimethyl-2-oxabicyclo[2.2.2]oct-5-ene;Dehydro-1,8-cineol;Dehydro-1,8-cineole;66113-06-2;1,8-Dehydrocineole;1,8-cineole dehydro;Dehydro-1,8-cyneole;Dehydro-1.8-cineole;2,3-Dehydro-1,8-cineol;1,8-Epoxy-p-menth-2-ene;1,8-Epoxy-p-mentha-2-ene;SCHEMBL23358702;DTXSID80335140;CHEBI:167365;1,3,3-Trimethyl-2-oxabicyclo[2.2.2]oct-5-ene #;Q67879829;92760-25-3

Chemical Property of 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]oct-5-ene

Chemical Property:

• Vapor Pressure: 1.24mmHg at 25°C
• Boiling Point: 180°C at 760 mmHg
• Flash Point: 55.6°C
• PSA: 9.23000
• Density: 0.948g/cm³
• LogP: 2.52010
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 205

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC(O1)(C=C2)C)C

Technology Process of 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]oct-5-ene

There total 2 articles about 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]oct-5-ene 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:

2-endo-hydroxy-1,8-cineole ((1R,6R)-1,3,3-trimethyl-2-oxabicyclo-[2.2.2]octan-6-ol) (18679-48-6,38223-62-0,38223-63-1,54164-88-4,60761-00-4,66965-45-5,92999-78-5,103665-39-0,109009-75-8) → 1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-5-ene (66113-06-2,92760-25-3) + isopinol + pinol (2437-97-0,89576-52-3)

Guidance literature:

With pyridine; potassium tert-butylate; phosphorus tribromide; Yield given. Multistep reaction; 1.) C₆H₆, RT, 60 h, 2.) DMSO, 48 h;

Reference yield:

(E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5,96680-15-8) → 1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-5-ene (66113-06-2,92760-25-3) + 1-methyl-4-isopropenylbenzene (1195-32-0) + p-mentha-1,3,8-triene (18368-95-1) + 4-methylisopropylbenzene (99-87-6) + 1-(1'-hydroxy-1'-methylethyl)-4-methylcyclohexa-1,3-diene (82538-84-9) + limonene. (138-86-3,555-08-8,8022-90-0,9003-73-0,95327-98-3)

Guidance literature:

With hydrogen; In n-heptane; at 70 ℃; for 6h; under 760.051 Torr;

DOI:10.1002/cssc.201000188

Reference yield:

(+/-)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-5-ene (63025-72-9,66113-06-2,88444-55-7,92760-25-3) → eucalyptol (470-82-6)

Guidance literature:

With hydrogen; platinum;

DOI:10.1016/S0040-4039(01)91066-4

upstream raw materials:

2-endo-hydroxy-1,8-cineole ((1R,6R)-1,3,3-trimethyl-2-oxabicyclo-[2.2.2]octan-6-ol)

(E/Z)-3,7-dimethyl-2,6-octadienal

Downstream raw materials:

eucalyptol