Ethanone, 1-(6-methyl-7-oxabicyclo[4.1.0]hept-3-yl)-, (3S)-[partial]- (9CI)

Base Information

• Chemical Name: Ethanone, 1-(6-methyl-7-oxabicyclo[4.1.0]hept-3-yl)-, (3S)-[partial]- (9CI)
• CAS No.: 203508-62-7
• Molecular Formula: C9H14 O2
• Molecular Weight: 154.209
• Mol file: 203508-62-7.mol

Synonyms:Ethanone, 1-(6-methyl-7-oxabicyclo[4.1.0]hept-3-yl)-, (3S)-[partial]- (9CI)

Chemical Property of Ethanone, 1-(6-methyl-7-oxabicyclo[4.1.0]hept-3-yl)-, (3S)-[partial]- (9CI)

Chemical Property:

• Boiling Point: 80 - 82 °C (1 mmHg)
• PSA: 29.60000
• LogP: 1.53300

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Ethanone, 1-(6-methyl-7-oxabicyclo[4.1.0]hept-3-yl)-, (3S)-[partial]- (9CI)

There total 3 articles about Ethanone, 1-(6-methyl-7-oxabicyclo[4.1.0]hept-3-yl)-, (3S)-[partial]- (9CI) 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: 89.0%

(-)-limonene oxide (203719-53-3) → 1-(3S)-(6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)ethanone (203508-62-7,1932365-85-9)

Guidance literature:

(-)-limonene oxide; With ozone; In methanol; dichloromethane; at -78 ℃;

With dimethylsulfide; In methanol; dichloromethane; Further stages.;

DOI:10.1016/j.tetlet.2004.01.121

Reference yield:

(-)-(S)-limonene (5989-54-8,555-08-8,8022-90-0,9003-73-0,95327-98-3) → 1-(3S)-(6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)ethanone (203508-62-7,1932365-85-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 80 percent / m-CPBA / CH₂Cl₂ / 20 °C

2.1: O₃ / CH₂Cl₂; methanol / -78 °C

2.2: 89 percent / Me₂S / CH₂Cl₂; methanol

With ozone; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;

DOI:10.1016/j.tetlet.2004.01.121

Reference yield:

C8H12O4 + acetic anhydride (108-24-7) → 1-(3S)-(6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)ethanone (203508-62-7,1932365-85-9)

Guidance literature:

C₈H₁₂O₄; With triethylamine; at -33 ℃; for 0.5h;

acetic anhydride; With dmap; at -33 - -5 ℃; for 1.5h;

DOI:10.1002/chem.201705656

upstream raw materials:

(-)-limonene oxide

(-)-(S)-limonene

acetic anhydride

Downstream raw materials:

(1S,2S,4R,6R)-4-Benzyloxy-2-ethynyl-1-methyl-7-oxa-bicyclo[4.1.0]heptane

(3R,4S,6S)-6-Benzyloxy-4-ethynyl-1-oxa-spiro[2.5]octane

(1R,2S,4S)-4-Benzyloxy-2-ethynyl-1-methyl-cyclohexanol

(1R,5R)-5-Benzyloxy-3-ethynyl-2-methyl-cyclohex-2-enol