16720-76-6

Basic information

• Product Name: 4-Benzyl-2,5-dihydrofuran-2-one
• Synonyms: 4-Benzyl-2(5H)-furanone;4-Benzyl-2,5-dihydrofuran-2-one;4-Benzylfuran-2(5H)-one
• CAS NO: 16720-76-6
• Molecular Formula: C₁₁H₁₀O₂
• Molecular Weight: 174.1959
• Mol File: 16720-76-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 354.5°Cat760mmHg
• Flash Point: 147.9°C
• Appearance: /
• Density: 1.194g/cm³
• Vapor Pressure: 3.34E-05mmHg at 25°C
• Refractive Index: 1.586
• CAS DataBase Reference: 4-Benzyl-2,5-dihydrofuran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Benzyl-2,5-dihydrofuran-2-one(16720-76-6)
• EPA Substance Registry System: 4-Benzyl-2,5-dihydrofuran-2-one(16720-76-6)

Safety Data

• Hazardous Substances Data: 16720-76-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 17, 1990 DOI: 10.1016/S0040-4039(00)94322-3

InChI:InChI=1/C11H10O2/c12-11-7-10(8-13-11)6-9-4-2-1-3-5-9/h1-5,7H,6,8H2

Upstream product

• 850856-43-8 4-benzyl-4-hydroxy-dihydro-furan-2-one 
• 90252-79-2 3-benzylbut-3-enoic acid 
• 103-80-0 phenylacetyl chloride 
• 408335-85-3 1-bromoacetoxy-3-phenyl-acetone 
• 36960-03-9 2-oxo-3-phenylpropyl acetate 
• 4250-02-6 1-diazo-3-phenyl-2-propanone 
• 74796-61-5 (E)-4-Methyl-5-phenyl-2-trimethylsilanyloxy-pent-3-enenitrile 
• 13910-25-3 3-Methyl-4-phenyl-but-2-enal 
• 96540-34-0 3-ethoxycarbonyl-4-(1-iodobenzyl)-4,5-dihydrofuran-2(3H)-one 
• 96540-46-4 4-benzyl-3-phenylthio-4,5-dihydrofuran-2(3H)-one 
• 96540-42-0 3-carbonyl-4-benzyl-4,5-dihydrofuran-2(3H)-one 
• 96540-38-4 3-ethoxycarbonyl-4-benzyl-4,5-dihydrofuran-2(3H)-one 
• 22530-98-9 4-benzyl-dihydro-furan-2-one 
• 30457-89-7 2-benzylallyl alcohol 

Downstream Products

• 22530-98-9 4-benzyl-dihydro-furan-2-one 
• 96847-64-2 5-phenyl-3-oxabicyclo<3.1.0>hexan-2-one 
• 112895-79-1 Sodium; 3-hydroxymethyl-4-phenyl-butyrate 
• 126434-65-9 (S)-(-)-β-benzyl-γ-butyrolactone 
• 126434-64-8 (R)-dihydro-4-(phenylmethyl)furan-2(3H)-one 

Relevant articles and documents

Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones

The oxidative cyclization of β-substituted β,γ-unsaturated carboxylic acids using a hypervalent iodine reagent to provide 4-substituted furan-2-one products, is reported. In this cyclization, the use of a highly electrophilic PhI(OTf) 2, which is in situ prepared from PhI(OAc) 2 and Me 3 SiOTf, is crucial. Depending on the substitution pattern at the α-position of the substrates, furan-2(5 H)-ones or furan-2(3 H)-ones are produced. Thus, the present method offers a useful tool for accessing various types of 4-substituted furan-2-ones that are important structural motifs in the field of organic chemistry and medicinal chemistry.

Preparation and reactions of 3,4-bisstannyl-2(5H)furanones

Bistributylstannyl-2(5H)-furanone 4a has been prepared from 3-(tetrahydropyran-2-yl)oxy but-2-ynoate and shown to exhibit good selectivity in its Stille reactions with a range of halogenated compounds, leading to 4-substituted-3-stannyl-2(5H)-furanones, in generally moderate yield. Under certain reaction conditions, doubly substituted products were also isolated from the reactions. The 3,4-bistrimethylstannyl furanone, 4b, corresponding to 4a was prepared, but decomposed during all attempts to execute Stille reactions upon it.

3-Phenylselanylfuran-2(5H)-one: A versatile building block in the synthesis of lignans. A new approach towards 3,4-dibenzyl γ-butyrolactones

Ready available 3-phenylselanylfuran-2(5H)-one undergoes tandem conjugate addition-alkylation by organocopper reagents to afford, with good yields and diastereoselectivities, 3,4-disubstituted-3-phenylselanyl-γ- butyrolactones, which can be transformed into naturally occurring compounds, such as lignans.