94540-79-1

Basic information

• Product Name: (E)-α-benzylidene-γ-phenyl-γ-butyrolactone
• Synonyms: (E)-α-benzylidene-γ-phenyl-γ-butyrolactone
• CAS NO: 94540-79-1
• Molecular Weight: 250.297
• Mol File: 94540-79-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (E)-α-benzylidene-γ-phenyl-γ-butyrolactone(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-α-benzylidene-γ-phenyl-γ-butyrolactone(94540-79-1)
• EPA Substance Registry System: (E)-α-benzylidene-γ-phenyl-γ-butyrolactone(94540-79-1)

Safety Data

• Hazardous Substances Data: 94540-79-1(Hazardous Substances Data)

Upstream product

• 1743-36-8 1-phenylbut-3-yn-1-ol 
• 100-52-7 benzaldehyde 
• 26613-71-8 4-phenyl-2-methylenebutyrolactone 
• 591-50-4 iodobenzene 
• 17572-78-0 1,4-diphenylbut-3-yn-1-ol 
• 1008788-92-8 (2-oxo-5-phenyltetrahydrofuran-3-yl)-phosphonic acid diethyl ester 
• 53949-11-4 γ-phenyl-α-phenylmethylene-Δ^β,γ-butenolide 
• 55980-63-7 Methyl-4-hydroxy-4-phenyl-2-butenoat 
• 69158-04-9 2-(Hydroxy-phenyl-methyl)-4-oxo-4-phenyl-butyric acid methyl ester 

Relevant articles and documents

A novel one pot synthesis of γ-butyrolactones

α-Arylidene-γ-phenyl-Δβ,γ-butenolides were converted to the respective γ-butyrolactones in methyl alcohol with sodium borohydride in presence of triethylamine in a single pot.

Synthesis and QSAR study of novel α-methylene-γ-butyrolactone derivatives as antifungal agents

Thirty-six new α-benzylidene-γ-lactone compounds based α-methylene-γ-butyrolactone substructure were prepared and characterized by spectroscopic analysis. All compounds were evaluated for antifungal activities in vitro against six plant pathogenic fungi and the half maximal inhibitory concentration (IC50) against Botrytis cinerea and Colletotrichum lagenarium were investigated. Compounds 5c-3 and 5c-5 with the halogen atom exhibited excellent fungicidal activity against B. cinerea (IC50?=?22.91, 18.89?μM). The structure-activity relationships (SARs) analysis indicated that the derivatives with electron-withdrawing substituents at the meta- or para-positions improves the activity. Via the heuristic method, the generated quantitative structure-activity relationship (QSAR) model (R2?=?0.961) revealed a strong correlation of antifungal activity against B. cinerea with molecular structures of these compounds. Meanwhile, the cytotoxicity of 20 representative derivatives was tested in the human tumor cells line (HepG2) and the hepatic L02 cells line, the result indicated that the synthesized compounds showed significant inhibitory activity and limited selectivity. Compound 5c-5 has the highest fungicidal activity with IC50?=?18.89?μM (against B. cinerea.) but low cytotoxicity with IC50?=?35.4?μM (against HepG2 cell line) and IC50?=?68.8?μM (against Hepatic L02 cell line). These encouraging results can be providing an alternative, promising use of α-benzylidene-γ-lactone through the design and exploration of eco-friendly fungicides with low toxicity and high efficiency.

CO2-activation for γ-butyrolactones and its application in the total synthesis of (±)-heteroplexisolide e

An efficient nickel(0)-catalyzed highly regio- and stereoselective hydrocarboxylation of homopropargylic alcohols with ZnEt2 in the presence of CO2 (1 atm, balloon) to synthesize α-alkylidene- γ-butyrolactones is described. The catal