58588-90-2

Basic information

• Product Name: α-bromomethyl-γ-butene lactone
• Synonyms: α-bromomethyl-γ-butene lactone
• CAS NO: 58588-90-2
• Molecular Weight: 176.997
• Mol File: 58588-90-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 80-85 °C(Press: 8 Torr)
• Density: 1.738±0.06 g/cm3(Predicted)
• CAS DataBase Reference: α-bromomethyl-γ-butene lactone(CAS DataBase Reference)
• NIST Chemistry Reference: α-bromomethyl-γ-butene lactone(58588-90-2)
• EPA Substance Registry System: α-bromomethyl-γ-butene lactone(58588-90-2)

Safety Data

• Hazardous Substances Data: 58588-90-2(Hazardous Substances Data)

Upstream product

• 917506-89-9 methyl 4-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylenebutyrate 
• 547-65-9 α-methylene-γ-butyrolactone 
• 109765-92-6 α-hydroxymethyl-γ-crotonolactone 
• 109765-91-5 4,5-dihydro-3-(1-hydroxymethyl)-3-phenylthio-3H-furan-2-one 

Downstream Products

• 1309689-82-4 C₁₂H₁₇NO₂S₂ 
• 1309689-87-9 C₁₃H₁₃NO₂S₂ 
• 1309689-88-0 C₁₂H₁₀ClNO₂S₂ 
• 1309689-78-8 C₈H₁₁NO₂S₂ 
• 1309689-86-8 C₁₂H₁₁NO₂S₂ 
• 1309689-89-1 C₁₃H₁₃NO₂S₂ 

Relevant articles and documents

Total syntheses of paraconic acids and 1,10-seco-guaianolides via a barbier allylation/translactonization cascade of 3-(Bromomethyl)-2(5H)-furanone

A palladium-catalyzed Barbier allylation/translactonization cascade reaction was established for the rapid construction of β,γdisubstituted α-exo-methylene-γ-butyrolactone, an important motif in sesquiterpenes. Dimethyl zinc played significant roles in bo

Rapid and scalable synthesis of chiral bromolactones as precursors to α-exo-methylene-γ-butyrolactone-containing sesquiterpene lactones

The sesquiterpene lactones cover a diverse and pharmacologically important diversity space. In particular, the electrophilic α-exo-methylene-γ-butyrolactone moiety that is preponderant in this natural product family has been shown to readily engage in cov

Asymmetric synthesis of β-substituted α-methylenebutyro-lactones via trip-catalyzed allylation: Mechanistic studies and application to the synthesis of (S)-(-)-hydroxymatairesinol

Asymmetric allylation of (hetero)aromatic aldehydes by a zinc(II)-allylbutyrolactone species catalyzed by a chiral BINOL-type phosphoric acid gave β-substituted α-methylenebutyrolactones in 68 to >99% ee and 52-91% isolated yield. DFT studies on the intermediate Zn 2+-complex - crucial for chiral induction - suggest a six-membered ring intermediate, which allows the phosphoric acid moiety to activate the aldehyde. The methodology was applied to the synthesis of the antitumour natural product (S)-(-)-hydroxymatairesinol.