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Merck
CN

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

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About This Item

Linear Formula:
(C6H5)3P=CHCOCH2CO2C2H5
CAS Number:
13148-05-5
Molecular Weight:
390.41
NACRES:
NA.22
PubChem Substance ID:
24866344
UNSPSC Code:
12352108
MDL number:
MFCD00192162
Assay:
97%

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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

SMILES string

CCOC(=O)CC(=O)C=P(c1ccccc1)(c2ccccc2)c3ccccc3

InChI key

QYXSFVCJCUXGJH-UHFFFAOYSA-N

assay

97%

reaction suitability

reaction type: C-C Bond Formation

functional group

ester, ketone, phosphine

Quality Level

100

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKBC6254V
MKBC6254
01209EJ
06911JD
32630JQ

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

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