ethyl 3-oxo-4-(triphenyl-$l^{5}-phosphanylidene)butanoate

• ChemBase ID: 74864
• Molecular Formular: C24H23O3P
• Molecular Mass: 390.411381
• Monoisotopic Mass: 390.13848123
• SMILES: P(=CC(=O)CC(=O)OCC)(c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: CCOC(=O)CC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: 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
• InChIKey: QYXSFVCJCUXGJH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 3-oxo-4-(triphenyl-$l^{5}-phosphanylidene)butanoate; ethyl 3-oxo-4-(triphenyl-λ^5-phosphanylidene)butanoate
• IUPAC Traditional name: ethyl 3-oxo-4-(triphenyl-$l^{5}-phosphanylidene)butanoate; ethyl 3-oxo-4-(triphenyl-λ^5-phosphanylidene)butanoate
• Synonyms: Ethyl 3-oxo-4-(triphenylphosphoranylidene)butyrate; [3-(Ethoxycarbonyl)-2-oxopropylidene]triphenylphosphorane; 3-Oxo-4-(triphenylphosphoranylidene)butanoic acid ethyl ester; 4-(Triphenylphosphoranylidene)acetoacetic acid ethyl ester; [3-(Ethoxycarbonyl)-2-oxopropylidene]triphenylphosphorane; Ethyl 3-oxo-4-(triphenylphosphoranylidene)butyrate; Ethyl 3-Oxo-4-(triphenylphosphoranylidene)butyrate; 2-氧-4-(三苯基膦)丁酸乙酯

Database IDs

• CAS Number: 13148-05-5
• MDL Number: MFCD00192162
• PubChem SID: 24866344; 162039782
• PubChem CID: 2734128

CALCULATED PROPERTIES

• Acid pKa: 11.046894
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.944699
• LogD (pH = 7.4): 5.944602
• Log P: 5.9447
• Molar Refractivity: 113.0929 cm^3
• Polarizability: 44.349445 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Methanol
• Apperance: Off-White Powder
• Melting Point: 103-104°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Irritant
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%
• Linear Formula: (C6H5)3P=CHCOCH2CO2C2H5

DETAILS

Sigma Aldrich - 420670

Packaging
5 g in glass bottle
Application
Can be coupled with glyoxals in a one-step route to 4-hydroxycyclopentanones.1 Also used to prepare 2H-pyran-2-ones from oxazolones.2
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 cyclocondensationReactant for preparation of:
• γ-(Dioxobutylidene)butenolides
• Chain conjugated 2H-pyran-5-carboxylates
• 2-Substituted pyridoacridines with antitumor activity by means of thermolysis

Toronto Research Chemicals - E925425

A useful synthetic intermediate in the production of antibiotics.