| Identification | Back Directory | [Name]
2-CYCLOPENTYLIDENECYCLOPENTANONE | [CAS]
825-25-2 | [Synonyms]
Loxoprofen Impurity 61
Bicyclopentyliden-2-one
BICYCLOPENTYLIDENE-2-ONE
Δ1,1'-Bicyclopentane-2-one
Δ1,1'-Bi[cyclopentane]-2-one
2-CYCLOPENTYLIDENECYCLOPENTANONE
1,1'-Bi(cyclopentylidene)]-2-one
cyclopentylidenecyclopentan-2-one
Cyclopentanone,2-cyclopentylidene-
2-CYCLOPENTYLIDENE-1-CYCLOPENTANONE
2-Cyclopentylidenecyclopentane-1-one
2-Cyclopentylidenecyclopentanone,97% | [EINECS(EC#)]
212-542-7 | [Molecular Formula]
C10H14O | [MDL Number]
MFCD00044678 | [MOL File]
825-25-2.mol | [Molecular Weight]
150.22 |
| Chemical Properties | Back Directory | [Melting point ]
74-75 °C | [Boiling point ]
231.78°C (rough estimate) | [density ]
1 g/cm3 | [refractive index ]
1.5215 (estimate) | [Fp ]
104°C | [storage temp. ]
2-8°C, protect from light | [Appearance]
Colorless to light yellow Liquid | [InChI]
InChI=1S/C10H14O/c11-10-7-3-6-9(10)8-4-1-2-5-8/h1-7H2 | [InChIKey]
NYSYNXRPXJZYFY-UHFFFAOYSA-N | [SMILES]
C1(=O)CCC/C/1=C1\CCCC\1 |
| Hazard Information | Back Directory | [Uses]
Bicyclopentylidene-2-one is derived from Cyclopentanone (C988395), which is a chemical compound used in the synthesis of various simple and complex organic compounds. Also, it is used in the synthesis of peptidase IV inhibitors for the treatment of type 2 diabetes. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 39, p. 1028, 1974 DOI: 10.1021/jo00922a002 | [Synthesis]
The synthesis of 2-cyclopentylidenecyclopentanone is a classic example of a self-condensation reaction, specifically an aldol condensation followed by dehydration. Under basic or acidic conditions, one molecule of cyclopentanone (C₅H₈O) is converted into its enolate, which nucleophilically attacks the carbonyl group of a second cyclopentanone molecule. The resulting β-hydroxy ketone intermediate undergoes dehydration to yield the α,β-unsaturated ketone product. Industrially, such transformations are often conducted under heterogeneous catalysis using solid acid–base bifunctional catalysts (e.g., Mg–Al hydrotalcites or mixed metal oxides) to improve selectivity and enable continuous-flow operation. The product is of interest as a model intermediate for high-density fuel candidates and has been explored in fragrance chemistry for its woody, amber-like odor. |
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