63678-00-2

Basic information

• Product Name: 2,2-dimethyl-5-phenyldihydrofuran-3(2H)-one
• Synonyms: 2,2-Dimethyl-5-phenyl-dihydro-furan-3-one; 3(2H)-Furanone, dihydro-2,2-dimethyl-5-phenyl-
• CAS NO: 63678-00-2
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.2384
• Mol File: 63678-00-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 296.9°C at 760 mmHg
• Flash Point: 129°C
• Density: 1.063g/cm³
• Vapor Pressure: 0.0014mmHg at 25°C
• Refractive Index: 1.515
• CAS DataBase Reference: 2,2-dimethyl-5-phenyldihydrofuran-3(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-dimethyl-5-phenyldihydrofuran-3(2H)-one(63678-00-2)
• EPA Substance Registry System: 2,2-dimethyl-5-phenyldihydrofuran-3(2H)-one(63678-00-2)

Safety Data

• Hazardous Substances Data: 63678-00-2(Hazardous Substances Data)

Usage

Usage

Commonly used as a flavoring agent and fragrance ingredient.

Odor description

Sweet, floral, and fruity.

Natural occurrence

Responsible for the characteristic smell and taste of a variety of fruits.

Applications

Often used in the production of flavors and fragrances for food and cosmetic products.

Potential uses

May have applications in the pharmaceutical industry and in organic synthesis.

Unique feature

Has a unique chemical structure.

Importance

2,2-dimethyl-5-phenyldihydrofuran-3(2H)-one has significant industrial and commercial uses, particularly in the creation of appealing scents and flavors.

Upstream product

• 35298-48-7 2,2-dimethyl-3(2H)-furanone 
• 23402-69-9 lithium diphenylcuprate 
• 86119-84-8 phosphoric acid 
• 63677-96-3 (E)-2-hydroxy-2-methyl-5-phenylpent-4-en-3-one 
• 129223-47-8 3-(2'-bromo-1'-phenylethoxy)-3-methylbutyne 
• 100-42-5 styrene 
• 100-52-7 benzaldehyde 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 88865-31-0 5-acetoxy-2-methyl-5-phenyl-3-pentyn-2-ol 
• 131354-47-7 4-methyl-1-phenyl-pent-2-yne-1,4-diol 
• 78957-35-4 3-acetoxy-2,2-dimethyl-5-phenyl-2,5-dihydrofuran 
• 4437-80-3 4,4-dimethyl-5-methylene-1,3-dioxolan-2-one 
• 123990-82-9 3-Benzyloxy-1-diazo-3-methyl-butan-2-one 
• 102939-67-3 2,2-dimethyl-3-methylene-5-phenyltetrahydrofuran 

Downstream Products

• 493-71-0 bullatenone 

Relevant articles and documents

α-Methylene Cyclic Carbonate as a Conjunctive Agent for Aromatic Aldehydes

α-Methylene cyclic carbonate undervent dacarboxylative cycliaddition to aromatic aldehydes to yield dihydrofuranone derivatives in the presence of a dicationic palladium complex.

Stereoelectronic effects in ring closure reactions: the 2'-hydroxychalcone-flavanone equilibrium, and related systems

The 2'-hydroxychalcone (2-HOC6H4COCH=CHC6H4X)-flavanone equilibrium in trifluoroacetic acid (TFA) has been examined.The influence of substituents X on the rate of attainment of equilibrium shows that the 6-endo-trig mode of ring closure by Michael addition is disallowed, by demonstrating a negative ρ value for the reaction rate when X is varied.Reaction therefore proceeds either on the carbonyl-protonated form, which allows twisting about the 2,3 double bond, its double bond character being reduced by resonance, or through direct rate-limiting protonation on the 2,3-double bond.Either pathway permits the allowed 6-exo-trig mode of ring closure to be followed.Alternative mechanism involving intermolecular Michael addition of trifluoroacetate, followed by intramolecular 6-exo-tet displacement are considered.Such Michael adducts can be detected in the ring closures of 2-crotonyl-4-methylphenol and 4,4-dimethyl-1-(2-hydroxyphenyl)-2-penten-1-one in TFA, but they do not appear to lie on the main pathway, because the reaction proceed with equal facility in methanesulphonic acid/chloroform medium, which does not contain a suitable nucleophile for such a mechanism.Further important mechanistic information is given by studying the reactions in TFA-d, together with measurements on the (E)-2-methyl-3-oxo-5-arylpent-4-en-2-ol and flight during the rate-limiting step, and provide evidence against the mechanism involving a preequilibrium carbonyl protonation, such as in the Nazarov rearrangement of 3'-methoxychalcones, where KH/kD is ca. 0.7.Some results are also reported for ring closure of the 2-aminochalcones in TFA.

Regiocontrolled Formation of 4,5-Dihydro-3(2H)-furanones from 2-Butyne-1,4-diol Derivatives. Synthesis of Bullatenone and Geiparvarin

Two new methods for selective hydration of 1,1,4-trisubstituted 2-butyne-1,4-diols (1) to give 4,5-dihydro-3(2H)-furanone derivatives are reported.The first involves selective monoacetylation of the less hindered hydroxyl group of 1 followed by Ag(I)-cata