1008788-92-8

Basic information

• Product Name: (2-oxo-5-phenyltetrahydrofuran-3-yl)-phosphonic acid diethyl ester
• Synonyms: (2-oxo-5-phenyltetrahydrofuran-3-yl)-phosphonic acid diethyl ester
• CAS NO: 1008788-92-8
• Molecular Weight: 298.276
• Mol File: 1008788-92-8.mol

Chemical Properties

• CAS DataBase Reference: (2-oxo-5-phenyltetrahydrofuran-3-yl)-phosphonic acid diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2-oxo-5-phenyltetrahydrofuran-3-yl)-phosphonic acid diethyl ester(1008788-92-8)
• EPA Substance Registry System: (2-oxo-5-phenyltetrahydrofuran-3-yl)-phosphonic acid diethyl ester(1008788-92-8)

Safety Data

• Hazardous Substances Data: 1008788-92-8(Hazardous Substances Data)

Upstream product

• 97554-76-2 2-(diethoxyphosphoryl)-4-oxo-4-phenylbutyric acid ethyl ester 

Downstream Products

• 946-39-4 ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate 
• 1008789-05-6 α-diethoxyphosphoryl-α-benzyl-γ-phenyl-γ-butyrolactone 
• 1008789-07-8 (3-(3-methylbut-2-enyl)-2-oxo-5-phenyltetrahydrofuran-3-yl)-phosphonic acid diethyl ester 
• 94540-79-1 (E)-α-benzylidene-γ-phenyl-γ-butyrolactone 
• 1037575-88-4 C₁₄H₁₆O₂ 

Relevant articles and documents

A general stereoselective method for the synthesis of cyclopropanecarboxylates. A new version of the homologous Horner-Wadsworth- Emmons reaction

The synthesis of α-, β- and γ-substituted α-phosphono-γ-lactones was accomplished using different ring closure and ring homologation strategies. It was found that the lactones could be selectively transformed into the corresponding ethyl cyclopropanecarboxylates by treatment with sodium ethoxide in boiling THF. The reported reaction provides an attractive alternative to the classical homologous Horner-Wadsworth-Emmons approach to the construction of cyclopropanes with electron-withdrawing functionalities. This journal is The Royal Society of Chemistry.

Synthesis and cytotoxic activity of γ-aryl substituted α-alkylidene-γ-lactones and α-alkylidene-γ-lactams

A series of 5-aryl-3-alkylidenedihydrofuran-2(3H)-ones 6a-g″ and 11a,b as well as 5-aryl-3-methylidenepyrrolidin-2-ones 10a-c and 12 were synthesized starting from 4-aryl-2-diethoxyphosphoryl-4-oxobutanoates 3a-g. Reaction sequence includes reduction or reductive amination of the carbonyl group, lactonization or lactamization step and finally the Horner-Wadsworth-Emmons olefination of aldehydes using thus obtained 5-aryl-3-diethoxyphosphoryl-3,4-dihydrofuran-2(5H)-ones 5a-g″ or 5-aryl-3-diethoxyphosphorylpyrrolidin-2-ones 9a-c. Furanones 6 and 11, as well as pyrrolidinones 10 and 12, were evaluated in vitro against mouse leukemia cell line L-1210 and two human leukemia cell lines HL-60 and NALM-6. Several of the obtained furanones proved to be very potent against all three cell lines with IC50 values lower than 6 μM. Structure-activity relationships of these compounds, as well as 5-alkyl or 5-arylmethyl-3-methylidenedihydrofuran-2(3H)-ones 13a-e, previously obtained in our laboratory, are discussed.