Spiro[5.5]undecane-2,4-dione

Base Information

• Chemical Name: Spiro[5.5]undecane-2,4-dione
• CAS No.: 1481-99-8
• Molecular Formula: C11H16 O2
• Molecular Weight: 180.247
• Hs Code.: 2914299000
• European Community (EC) Number: 882-489-8
• DSSTox Substance ID: DTXSID20407017
• Wikidata: Q82212224
• Mol file: 1481-99-8.mol

Synonyms:spiro[5.5]undecane-2,4-dione;1481-99-8;SCHEMBL1177140;spiro[5,5]undecane-2,4-dione;DTXSID20407017;LKFBIHAJCFDIIN-UHFFFAOYSA-N;BAA48199;MFCD03844396;AKOS008987434;SB33741;BS-13732;CS-0308737;FT-0761366;EN300-12955;A911329;Z85928737;F2124-0756

Chemical Property of Spiro[5.5]undecane-2,4-dione

Chemical Property:

• Vapor Pressure: 0.000181mmHg at 25°C
• Boiling Point: 317.6°Cat760mmHg
• Flash Point: 134.6°C
• PSA: 34.14000
• Density: 1.11g/cm³
• LogP: 2.25900
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 180.115029749
• Heavy Atom Count: 13
• Complexity: 219

Purity/Quality:

97% ^*data from raw suppliers

Spiro[5.5]undecane-2,4-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2(CC1)CC(=O)CC(=O)C2
• Uses: Spiro[5.5]undecane-2,4-dione, is used as a reactant in the production of hydroxy-dimethyl-oxo-cyclohexenyl-dimethyl-tetrahydro-xanthenone which is an oral neuropeptide Y5 receptor antagonist.

Technology Process of Spiro[5.5]undecane-2,4-dione

There total 13 articles about Spiro[5.5]undecane-2,4-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:

1-cyclohexylidene-2-propanone (874-68-0) → spiro[5.5]undecane-2,4-dione (1481-99-8)

Guidance literature:

Multi-step reaction with 3 steps

1: EtONa / ethanol / 6 h / Heating

2: 2 N NaOH / 2 h / Heating

3: 5 N H₂SO₄ / 4.5 h / Heating

With sodium hydroxide; sulfuric acid; sodium ethanolate; In ethanol;

DOI:10.1021/jm00097a001

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → spiro[5.5]undecane-2,4-dione (1481-99-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 14 percent / 50percent aq. NaOH / 72 h / Ambient temperature

2: EtONa / ethanol / 6 h / Heating

3: 2 N NaOH / 2 h / Heating

4: 5 N H₂SO₄ / 4.5 h / Heating

With sodium hydroxide; sulfuric acid; sodium ethanolate; In ethanol;

DOI:10.1021/jm00097a001

Reference yield:

C12H14O4(2-)*2Na(1+) → spiro[5.5]undecane-2,4-dione (1481-99-8)

Guidance literature:

With sulfuric acid; for 4.5h; Yield given; Heating;

DOI:10.1021/jm00097a001

upstream raw materials:

sodium ethanolate

2,4-dioxo-spiro[5.5]undecane-1-carboxylic acid ethyl ester

1-cyclohexenylacetone

diethyl malonate

Downstream raw materials:

1-carboxycyclohexylacetic acid

(1-acetonyl-cyclohexyl)-acetic acid

C₁₇H₁₉IO₂

2-(Benzyloxycarbonyloxy)-4-hydroxy-spiro<5.5>undeca-1,4-dien-3-on

Refernces