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420670

Sigma-Aldrich

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

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About This Item

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

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

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

420670-VAR:
420670-25G:
420670-BULK:
420670-5G:

Certificates of Analysis (COA)

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Synthesis, 453-453 (1992)
Tetrahedron Letters, 34, 4837-4837 (1993)

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