2-Oxaspiro[4.4]nonane-1,3-dione

Base Information

• Chemical Name: 2-Oxaspiro[4.4]nonane-1,3-dione
• CAS No.: 5623-90-5
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• Hs Code.: 2914299000
• European Community (EC) Number: 871-675-4
• DSSTox Substance ID: DTXSID70371835
• Nikkaji Number: J1.203.101G
• Wikidata: Q82159304
• Mol file: 5623-90-5.mol

Synonyms:2-oxaspiro[4.4]nonane-1,3-dione;5623-90-5;SCHEMBL347199;DTXSID70371835;HOKKSYPZFBKQAZ-UHFFFAOYSA-N;BBL011069;MFCD00661793;STK802261;2-oxa-spiro[4,4]nonane-1,3-dione;2-oxa-spiro[4.4]nonane-1,3-dione;AKOS001281093;AS-9639;LS-99617;CS-0224912;EN300-12180;A913578;Z104506022

Chemical Property of 2-Oxaspiro[4.4]nonane-1,3-dione

Chemical Property:

• Vapor Pressure: 0.000603mmHg at 25°C
• Refractive Index: 1.505
• Boiling Point: 310.4°Cat760mmHg
• Flash Point: 150.2°C
• PSA: 43.37000
• Density: 1.23g/cm³
• LogP: 1.02030
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 154.062994177
• Heavy Atom Count: 11
• Complexity: 213

Purity/Quality:

99%min ^*data from raw suppliers

2-Oxaspiro[4.4]nonane-1,3-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2(C1)CC(=O)OC2=O

Technology Process of 2-Oxaspiro[4.4]nonane-1,3-dione

There total 7 articles about 2-Oxaspiro[4.4]nonane-1,3-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: 70.0%

1-(carboxymethyl)cyclopentanecarboxylic acid (62953-73-5) → 2-oxaspiro[4.4]nonane-1,3-dione (5623-90-5)

Guidance literature:

With acetyl chloride; for 3h; Reflux;

DOI:10.2174/1570180816666190710130119

Reference yield:

1-methylcyclopentanecarboxylic acid (5217-05-0) + molybdenum hexacarbonyl (13939-06-5,199620-15-0) → 2-oxaspiro[4.4]nonane-1,3-dione (5623-90-5)

Guidance literature:

With N-[2-(phenylsulfanyl)ethyl]acetamide; palladium diacetate; silver nitrate; at 80 ℃; for 24h;

DOI:10.1002/anie.202104645

Reference yield:

ethyl 2-cyano-2-cyclopentylideneacetate (5407-83-0) → 2-oxaspiro[4.4]nonane-1,3-dione (5623-90-5)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. ethanol / 96 h / Ambient temperature

2: HCl, AcOH / H₂O / 48 h / Heating

3: AcCl / 3 h / Heating

With hydrogenchloride; acetic acid; acetyl chloride; In ethanol; water;

upstream raw materials:

1-(carboxymethyl)cyclopentanecarboxylic acid

ethyl 2-cyano-2-cyclopentylideneacetate

ethyl 2-cyano-2-(1-cyanocyclopentyl)acetate

cyclopentanone

Downstream raw materials:

1-(4-ethyl-phenacyl)-cyclopentanecarboxylic acid

2-oxaspiro[4,4]nonan-1-one

1-[2-(4-tert-Butyl-phenyl)-2-oxo-ethyl]-cyclopentanecarboxylic acid

1-[2-(3,4-Dimethyl-phenyl)-2-oxo-ethyl]-cyclopentanecarboxylic acid

Refernces

• 1、 Für, Csilla Sepsey,Riszter, Gergo,Gerencsér, János,Szigetvári, áron,Dékány, Miklós,Hazai, László,Keglevich, Gy?rgy,B?lcskei, Hedvig. "Synthesis of spiro[cycloalkane-pyridazinones] with high Fsp3 character". . p. 731 - 744. Retrieved 2020/06/22.
• 2、 Borenstein, Michael R.,Abou-Gharbia, Magid A.,Doukas, Peter H.. "SYNTHESIS OF SPIROIMIDES OF PHARMACOLOGIC INTEREST". . p. 2433 - 2438. Retrieved 2007/10/02.