420670

Ethyl 3-oxo-4-(triphenylphosphoranylidene)butyrate

97%

• Synonym(s): 3-Oxo-4-(triphenylphosphoranylidene)butanoic acid ethyl ester, 4-(Triphenylphosphoranylidene)acetoacetic acid ethyl ester, [3-(Ethoxycarbonyl)-2-oxopropylidene]triphenylphosphorane
• Linear Formula: (C₆H₅)₃P=CHCOCH₂CO₂C₂H₅
• CAS Number: 13148-05-5
• Molecular Weight: 390.41
• MDL number: MFCD00192162
• UNSPSC Code: 12352108
• PubChem Substance ID: 24866344
• NACRES: NA.22

Properties

• Assay: 97%
• reaction suitability: reaction type: C-C Bond Formation
• SMILES string: CCOC(=O)CC(=O)C=P(c1ccccc1)(c2ccccc2)c3ccccc3
• InChI: 1S/C24H23O3P/c1-2-27-24(26)18-20(25)19-28(21-12-6-3-7-13-21,22-14-8-4-9-15-22)23-16-10-5-11-17-23/h3-17,19H,2,18H2,1H3
• InChI key: QYXSFVCJCUXGJH-UHFFFAOYSA-N

Description

Application

Can be coupled with glyoxals in a one-step route to 4-hydroxycyclopentanones. Also used to prepare 2H-pyran-2-ones from oxazolones.

Reactant for stereoselective synthesis of:

• Polysubstituted cyclopentanones via double Michael addition reactions
• Hydroindanes via asymmetric quadruple aminocatalytic three-component domino condensation and spirocyclization
• Oxocyclohexenecarboxylates by cyclocondensation

Reactant for preparation of:

• γ-(Dioxobutylidene)butenolides
• Chain conjugated 2H-pyran-5-carboxylates
• 2-Substituted pyridoacridines with antitumor activity by means of thermolysis

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves