135366-64-2

Basic information

• Product Name: 2(3H)-Furanone, 3-acetyldihydro-3-hydroxy- (9CI)
• Synonyms: 2(3H)-Furanone, 3-acetyldihydro-3-hydroxy- (9CI)
• CAS NO: 135366-64-2
• Molecular Formula: C₆H₈O₄
• Molecular Weight: 144.12532
• Product Categories: ACETYLGROUP
• Mol File: 135366-64-2.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2(3H)-Furanone, 3-acetyldihydro-3-hydroxy- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone, 3-acetyldihydro-3-hydroxy- (9CI)(135366-64-2)
• EPA Substance Registry System: 2(3H)-Furanone, 3-acetyldihydro-3-hydroxy- (9CI)(135366-64-2)

Safety Data

• Hazardous Substances Data: 135366-64-2(Hazardous Substances Data)

Upstream product

• 517-23-7 3-acetyl-2-oxo-4,5-dihydrofuran 
• 100-42-5 styrene 

Downstream Products

• 13045-13-1 3-chloro-3-acetylpropanol 

Relevant articles and documents

1,5,7-Triazabicyclo[4.4.0]dec-5-ene Enhances Activity of Peroxide Intermediates in Phosphine-Free α-Hydroxylation of Ketones

The critical role of double hydrogen bonds was addressed for the aerobic α-hydroxylation of ketones catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), in the absence of either a metal catalyst or phosphine reductant. Experimental and theoretical investigations were performed to study the mechanism. In addition to initiating the reaction by proton abstraction, a more important role of TBD was revealed, that is, to enhance the oxidizing ability of peroxide intermediates, allowing DMSO to be used rather than commonly used phosphine reductants. Further characterizations with nuclear Overhauser effect spectroscopy (NOESY) confirmed the presence of double hydrogen bonds between TBD and the ketone, and kinetic studies suggested the attack of dioxygen on the TBD-enol adduct to be the rate-determining step. This work should encourage the application of TBD as a catalyst for oxidations.

Formation of δ-Lactones by cyanide catalyzed rearrangement of α-Hydroxy-β-oxoesters

δ-Valerolactone derivatives are formed by cyanide-catalyzed ring-transformation of cyclic α-hydroxy-β-oxoesters. This unprecedented reaction defines a new synthetic methodology, and the products are obtained in up to quantitative yields. Several alkyl substitutions as well as different ester residues are tolerated. Furthermore, benzo- and heteroarene-annulated starting materials are converted without problems. As an additional benefit, the starting materials are straightforwardly accessed by cerium-catalyzed aerobic α-hydroxylation of readily available β-oxoesters.

Aerobic α-hydroxylation of β-keto esters and amides by co-catalysis of SmI3 and I2 under mild base-free conditions

A clean base-free α-hydroxylation of β-keto esters and amides has been developed, in which air was used as the oxygen source and SmI3 and I2 were applied as the catalysts, affording the corresponding α-hydroxylated 1,3-dicarbonyl pro