52216-89-4

Basic information

• Product Name: 2(3H)-Furanone, dihydro-3-propylidene-, (Z)-
• CAS NO: 52216-89-4
• Molecular Formula: C7H10O2
• Mol File: 52216-89-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2(3H)-Furanone, dihydro-3-propylidene-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone, dihydro-3-propylidene-, (Z)-(52216-89-4)
• EPA Substance Registry System: 2(3H)-Furanone, dihydro-3-propylidene-, (Z)-(52216-89-4)

Safety Data

• Hazardous Substances Data: 52216-89-4(Hazardous Substances Data)

Upstream product

• 96-48-0 4-butanolide 
• 123-38-6 propionaldehyde 
• 109-94-4 formic acid ethyl ester 
• 2907-85-9 3-diethylphosphono-2-oxo-tetrahydrofuran 
• 14032-62-3 2-mercapto-γ-butyrolactone 
• 66909-41-9 O-ethyl S-(tetrahydro-2-oxo-3-furanyl) thiocarbonate 
• 51270-64-5 sodium salt of (Z)-3-(hydroxymethylene)dihydro-2(3H)-furanone 

Downstream Products

• 52216-90-7 (E)-α-propylidene-γ-butyrolactone 
• 55232-22-9 (R)-(-)-2-n-Propyl-γ-butyrolactone 
• 103411-93-4 (S)-3-Propyl-dihydro-furan-2-one 

Relevant articles and documents

Stereocontrol in Horner-Wadsworth-Emmons Condensations of α-Phosphono Lactones with Aldehydes: A Synthesis of Integerrinecic Acid and Senecic Acid Lactones

The Horner-Wadsworth-Emmons condensations of α-phosphono lactones were investigated under a variety of conditions.Upon treatment with KHMDS and 18-crown-6 in THF, condensations of the five-membered ring phosphono lactones 7a and 8 with propionaldehyde afforded the E olefins cleanly.In contrast, these phosphonates gave predominantly the Z olefins upon treatment with propionaldehyde, K2CO3 and 18-crown-6 in THF.A similar, though somewhat less-pronounced trend was observed with the six-membered ring phosphono lactone 9a.However, in its condensation with acetaldehyde the more functionalized phosphono lactone 4 gave the best E selectivity (ca. 9:1) when DBU/CH3CN was used, providing the methyl ester of integerrinecic acid lactone (5) in 77percent isolated yield.When K2CO3/18-crown-6/toluene was employed in a parallel reaction, only slight selectivity for the Z isomer was observed, but the methyl ester of senecic acid lactone (6) still was obtained in 43-46percent yield from the product mixture.

Convenient Synthesis of α-Epoxylactones (4-Oxo-1,5-dioxaspiroheptanes and -octanes)

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New Methods for Stereoselective Synthesis of α-Alkylidene-γ-butyrolactones Using Monoanion of O-Ethyl S-(Tetrahydro-2-oxo-3-furanyl) Thiocarbonate and Dianion of α-Mercapto-γ-butyrolactone

The lithium enolates of O-ethyl S-(tetrahydro-2-oxo-3-furanyl) dithiocarbonate and thiocarbonate were found to be efficient reagents for the stereoselective synthesis of α-alkylidene-γ-butyrolactones from carbonyl compounds.The dianion of α-mercapto-γ-butyrolactone was successfully generated by treatment of α-mercapto-γ-butyrolactone with 2.2 equivalents of lithium diisopropylamide in the presence of N,N,N',N'-tetramethylethylenediamine at -78 deg C in THF.The dianion thus formed has been utilized for the efficient and stereoselective synthesis of α-alkylidene-γ-butyrolactones from carbonyl compounds.