Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-acetyl-, (1S,2R,3S,4R)- (9CI)

Base Information

• Chemical Name: Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-acetyl-, (1S,2R,3S,4R)- (9CI)
• CAS No.: 587875-56-7
• Molecular Formula: C10H12O2
• Molecular Weight: 164.20108
• Mol file: 587875-56-7.mol

Synonyms:Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-acetyl-, (1S,2R,3S,4R)- (9CI)

Chemical Property of Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-acetyl-, (1S,2R,3S,4R)- (9CI)

Chemical Property:

• PSA: 0.00000
• LogP: 0.00000

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-acetyl-, (1S,2R,3S,4R)- (9CI)

There total 8 articles about Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-acetyl-, (1S,2R,3S,4R)- (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: 82.0%

1-oxo-2(Z)-penten-4-one (34218-22-9) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1R,2S,3R,4S)-3-Acetyl-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (85806-33-3,129568-34-9,129568-35-0,220191-57-1,220191-58-2,587875-56-7)

Guidance literature:

In dichloromethane; at 25 ℃; for 2h;

DOI:10.1021/jo952284p

Reference yield:

2-methylfuran (534-22-5) → (1R,2S,3R,4S)-3-Acetyl-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (85806-33-3,129568-34-9,129568-35-0,220191-57-1,220191-58-2,587875-56-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C

2: 82 percent / CH₂Cl₂ / 2 h / 25 °C

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jo952284p

Reference yield:

2-methylfuran (534-22-5) → (1R,2S,3R,4S)-3-Acetyl-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (85806-33-3,129568-34-9,129568-35-0,220191-57-1,220191-58-2,587875-56-7)

Guidance literature:

Multi-step reaction with 2 steps

1: m-CPBA / CH₂Cl₂ / 0 °C

2: 20 °C

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1: Ring cleavage / 2: Cycloaddition;

DOI:10.1016/S0040-4020(99)00997-7

upstream raw materials:

1-oxo-2(Z)-penten-4-one

cyclopenta-1,3-diene

2-methylfuran

2,5-dihydro-2,5-dimethoxy-2-methylfuran