22173-37-1

Basic information

• Product Name: 5-Phenyl-3,5-dimethyl-4,5-dihydro-2(3H)-furanone
• Synonyms: 5-Phenyl-3,5-dimethyl-4,5-dihydro-2(3H)-furanone
• CAS NO: 22173-37-1
• Molecular Weight: 190.242
• Mol File: 22173-37-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 5-Phenyl-3,5-dimethyl-4,5-dihydro-2(3H)-furanone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Phenyl-3,5-dimethyl-4,5-dihydro-2(3H)-furanone(22173-37-1)
• EPA Substance Registry System: 5-Phenyl-3,5-dimethyl-4,5-dihydro-2(3H)-furanone(22173-37-1)

Safety Data

• Hazardous Substances Data: 22173-37-1(Hazardous Substances Data)

Upstream product

• 80-62-6 methacrylic acid methyl ester 
• 98-86-2 acetophenone 
• 4743-74-2 2-phenylpent-4-en-2-ol 
• 201230-82-2 carbon monoxide 
• 802294-64-0 propionic acid 
• 98-83-9 isopropenylbenzene 
• 98-82-8 Isopropylbenzene 
• 97-63-2 methyl methacrylate 
• 107-12-0 propiononitrile 

Relevant articles and documents

A highly efficient asymmetric synthesis of optically active α,γ-substituted γ-butyrolactones using a chiral auxiliary derived from isosorbide

(equation presented) Using an easily accessible and inexpensive chiral auxiliary derived from isosorbide, optically active α,γ-substituted γ-butyrolactones were obtained in high enantiomeric purity (up to >99% ee for trans) by the Sml2-induced

Copper-Catalyzed Formal [2+2+1] Heteroannulation of Alkenes, Alkylnitriles, and Water: Method Development and Application to a Total Synthesis of (±)-Sacidumlignan D

A copper-catalyzed three-component reaction of alkenes, alkylnitriles, and water affords γ-butyrolactones in good yields. The domino process involves an unprecedented hydroxy-cyanoalkylation of alkenes and subsequent lactonization with the creation of three chemical bonds and a quaternary carbon center. The synthetic potential of this novel [2+2+1] heteroannulation reaction was illustrated by a concise total synthesis of (±)-sacidumlignan D.

Trimethylsilyl Cyanide - A Reagent for Umpolung, XX. - On the Regioselectivity of the Addition of Carbonyl Compounds to α,β-Unsaturated Aldehydes after Umpolung

By addition of tBuMe2SiCN to α,β-unsaturated aldehydes 5 the silylated cyanohydrins 6 are produced.Deprotonation of 6 provides allylic anions which can be attached to aldehydes and ketones in α-position (kinetic control) (-> 8) or γ-position (thermodynamic control) (-> 9).In contrast to the Me3Si group which has been applied so far the tBuMe2Si group is stable under the reaction conditions.Therefore, the ratio of α/γ adducts can be tuned from > 95:5 to 5:95 depending on the substitution pattern of 6, the aldehydes and ketones, the reaction time and temperature, and even by some additives.The γ adducts 9 are easily transformed into γ-butyrolactones 27 by acidic hydrolysis. Key Words: Umpolung / Regioselectivity / Substituent effects / Acylation, nucleophilic / Aldehydes, α,β-unsaturated / Trimethylsilyl cyanide