2-Azaspiro[4.4]non-1-ene

Base Information

• Chemical Name: 2-Azaspiro[4.4]non-1-ene
• CAS No.: 94695-94-0
• Molecular Formula: C₈H₁₃N
• Molecular Weight: 123.198
• Mol file: 94695-94-0.mol

Synonyms:

Chemical Property of 2-Azaspiro[4.4]non-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Azaspiro[4.4]non-1-ene

There total 5 articles about 2-Azaspiro[4.4]non-1-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: 15.0%

4-(4-bromobutyl)-1-(phenylsulfonyl)-2,3-dihydro-1H-pyrrole (156222-36-5) → 2-azaspiro<4.4>non-1-ene (94695-94-0) + phenyl pyrrolidine-3-spirocyclopentan-1-yl sulfone

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ja408387d

Reference yield:

3-(4-(tert-butyldimethylsilyloxy)butyl)-1-(phenylsulfonyl)pyrrolidin-2-one → 2-azaspiro<4.4>non-1-ene (94695-94-0) + phenyl pyrrolidine-3-spirocyclopentan-1-yl sulfone

Guidance literature:

Multi-step reaction with 5 steps

1: diisobutylaluminium hydride / hexane; tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

2: citric acid / toluene / 4 h / 80 °C / Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

4: carbon tetrabromide; triphenylphosphine / dichloromethane / 2 h / 0 °C / Inert atmosphere

5: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / benzene / 0.5 h / 80 °C / Inert atmosphere

With 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; triphenylphosphine; citric acid; In tetrahydrofuran; hexane; dichloromethane; toluene; benzene;

DOI:10.1021/ja408387d

Reference yield:

C20H35NO4SSi → 2-azaspiro<4.4>non-1-ene (94695-94-0) + phenyl pyrrolidine-3-spirocyclopentan-1-yl sulfone

Guidance literature:

Multi-step reaction with 4 steps

1: citric acid / toluene / 4 h / 80 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

3: carbon tetrabromide; triphenylphosphine / dichloromethane / 2 h / 0 °C / Inert atmosphere

4: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / benzene / 0.5 h / 80 °C / Inert atmosphere

With 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; triphenylphosphine; citric acid; In tetrahydrofuran; dichloromethane; toluene; benzene;

DOI:10.1021/ja408387d

upstream raw materials:

4-(1-Benzenesulfonyl-4,5-dihydro-1H-pyrrol-3-yl)-butan-1-ol

4-(4-bromobutyl)-1-(phenylsulfonyl)-2,3-dihydro-1H-pyrrole

Downstream raw materials:

2-azaspiro<4.4>nonane