1-Azaspiro[4.4]nonane-2,6-dione

Base Information

• Chemical Name: 1-Azaspiro[4.4]nonane-2,6-dione
• CAS No.: 187106-12-3
• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 153.181
• DSSTox Substance ID: DTXSID90447965
• Nikkaji Number: J2.184.358J
• Mol file: 187106-12-3.mol

Synonyms:1-Azaspiro[4.4]nonane-2,6-dione;187106-12-3;1-azaspiro[4.4]nonane-2,9-dione;1-Azaspiro[4.4]nonane-2,6-dione(9CI);DTXSID90447965

Chemical Property of 1-Azaspiro[4.4]nonane-2,6-dione

Chemical Property:

• PSA: 49.66000
• LogP: 0.66410
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 153.078978594
• Heavy Atom Count: 11
• Complexity: 224

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)C2(C1)CCC(=O)N2

Technology Process of 1-Azaspiro[4.4]nonane-2,6-dione

There total 3 articles about 1-Azaspiro[4.4]nonane-2,6-dione 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: 80.0%

3-(1-Nitro-2-oxo-cyclopentyl)-propionic acid methyl ester (180521-22-6) → 1-azaspiro[4.4]nonane-2,6-dione (187106-12-3,187106-14-5,187106-15-6)

Guidance literature:

With acetic acid; zinc; In ethanol; for 5h; Heating;

DOI:10.1016/S0957-4166(96)00509-5

Reference yield:

3-(2-Acetoxy-1-cyclopentenyl)-propionsaeure-methylester (58859-99-7) → 1-azaspiro[4.4]nonane-2,6-dione (187106-12-3,187106-14-5,187106-15-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / NH₄NO₃, TFA / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 80 percent / Zn, AcOH / ethanol / 5 h / Heating

With ammonium nitrate; acetic acid; trifluoroacetic acid; zinc; In ethanol; dichloromethane;

DOI:10.1016/S0957-4166(96)00509-5

Reference yield:

methyl 3-(2-oxo-cyclopentyl)propanoate (58712-11-1,10407-36-0) → 1-azaspiro[4.4]nonane-2,6-dione (187106-12-3,187106-14-5,187106-15-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / p-TsOH / 110 °C

2: 68 percent / NH₄NO₃, TFA / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 80 percent / Zn, AcOH / ethanol / 5 h / Heating

With ammonium nitrate; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; zinc; In ethanol; dichloromethane;

DOI:10.1016/S0957-4166(96)00509-5

upstream raw materials:

3-(1-Nitro-2-oxo-cyclopentyl)-propionic acid methyl ester

3-(2-Acetoxy-1-cyclopentenyl)-propionsaeure-methylester

methyl 3-(2-oxo-cyclopentyl)propanoate

Downstream raw materials:

(S)-1-azaspiro[4.4]nonane-2,6-dione

(-)-1-azaspiro[4.4]nonane-2,6-dione