3-Acetoxy-2,2,6-trimethyl-6-vinyltetrahydropyran

Base Information

• Chemical Name: 3-Acetoxy-2,2,6-trimethyl-6-vinyltetrahydropyran
• CAS No.: 67674-42-4
• Molecular Formula: C₁₂H₂₀O₃
• Molecular Weight: 212.289
• European Community (EC) Number: 266-881-0
• DSSTox Substance ID: DTXSID90886855
• Nikkaji Number: J333.294B
• Wikidata: Q82865796
• Mol file: 67674-42-4.mol

Synonyms:67674-42-4;3-Acetoxy-2,2,6-trimethyl-6-vinyltetrahydropyran;2H-Pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl-, 3-acetate;EINECS 266-881-0;56752-50-2;56779-64-7;Tetrahydro-2,2,6-trimethyl-6-vinyl-2H-pyran-3-yl acetate;2H-Pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl-, acetate;2H-Pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl-, acetate, trans-;2H-Pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl-, acetate, (3R,6R)-rel-;2H-Pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl-, acetate, (3R,6S)-rel-;2H-Pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl-, acetate, cis-;2H-Pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl-, 3-acetate, (3R,6R)-rel-;2H-Pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl-, 3-acetate, (3R,6S)-rel-;SCHEMBL11034667;DTXSID90886855;(6-Ethenyl-2,2,6-trimethyloxan-3-yl)acetate;3-acetoxy-2,2,6-trimethyl-6-vinyl-tetrahydropyran;3-Acetoxytetrahydro-2,2,6-trimethyl-6-vinyl-2H-pyran

Chemical Property of 3-Acetoxy-2,2,6-trimethyl-6-vinyltetrahydropyran

Chemical Property:

• Vapor Pressure: 0.035mmHg at 25°C
• Boiling Point: 241.9°C at 760 mmHg
• Flash Point: 94.4°C
• PSA: 35.53000
• Density: 0.98g/cm³
• LogP: 2.45180
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 212.14124450
• Heavy Atom Count: 15
• Complexity: 270

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCC(OC1(C)C)(C)C=C

Technology Process of 3-Acetoxy-2,2,6-trimethyl-6-vinyltetrahydropyran

There total 5 articles about 3-Acetoxy-2,2,6-trimethyl-6-vinyltetrahydropyran 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: 73.0%

(6R,2E)-6-Acetoxy-7-hydroxy-3,7-dimethyloct-2-en-1-yl N-Phenylcarbamate (136937-07-0) → Acetic acid (R)-2,2,6-trimethyl-6-vinyl-tetrahydro-pyran-3-yl ester (56752-50-2,56779-64-7,67674-42-4,137035-98-4,137035-99-5)

Guidance literature:

With tin(IV) chloride; In dichloromethane; a) 5 deg C, 5min, b) r.t., 18 h;

DOI:10.1055/s-1991-26542

Reference yield: 73.0%

(6S,2E)-6-Acetoxy-7-hydroxy-3,7-dimethyloct-2-en-1-yl N-Phenylcarbamate (136937-06-9) → Acetic acid (S)-2,2,6-trimethyl-6-vinyl-tetrahydro-pyran-3-yl ester (56752-50-2,56779-64-7,67674-42-4,137035-98-4,137035-99-5)

Guidance literature:

With tin(IV) chloride; In dichloromethane; a) 5 deg C, 5 min, b) r.t., 18 h;

DOI:10.1055/s-1991-26542

Reference yield: 53.0%

3-hydroxy-2,2,6-trimethyl-6-vinyltetrahydropyran (14049-11-7) + acetyl chloride (75-36-5) → 3-acetate-6-ethenyltetrahydro-2,2,6-trimethyl-2H-pyran-3-ol (67674-42-4,137035-98-4)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 - 20 ℃;

DOI:10.1007/BF02033674

upstream raw materials:

(6R,2E)-6-Acetoxy-7-hydroxy-3,7-dimethyloct-2-en-1-yl N-Phenylcarbamate

(6R,2E)-6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl phenylcarbamate

(6S,2E)-6-Acetoxy-7-hydroxy-3,7-dimethyloct-2-en-1-yl N-Phenylcarbamate

(6S,2E)-6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl phenylcarbamate

Downstream raw materials:

3-oxo-2,2,6-trimethyl-6-vinyltetrahydropyran

3-hydroxy-2,2,6-trimethyl-6-vinyltetrahydropyran