13133-96-5

Basic information

• Product Name: 5,5-dimethyl-4-phenyldihydrofuran-2(3H)-one
• Synonyms: 2(3H)-furanone, dihydro-5,5-dimethyl-4-phenyl-; 5,5-Dimethyl-4-phenyldihydrofuran-2(3H)-one
• CAS NO: 13133-96-5
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.2384
• Mol File: 13133-96-5.mol

Chemical Properties

• Boiling Point: 324.4°C at 760 mmHg
• Flash Point: 133.8°C
• Density: 1.063g/cm³
• Vapor Pressure: 0.000246mmHg at 25°C
• Refractive Index: 1.515
• CAS DataBase Reference: 5,5-dimethyl-4-phenyldihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-dimethyl-4-phenyldihydrofuran-2(3H)-one(13133-96-5)
• EPA Substance Registry System: 5,5-dimethyl-4-phenyldihydrofuran-2(3H)-one(13133-96-5)

Safety Data

• Hazardous Substances Data: 13133-96-5(Hazardous Substances Data)

Upstream product

• 81391-08-4 2,2-dimethyl-3-phenylcyclobutanone 
• 126641-73-4 methyl 3-hydroxy-4-methyl-3-phenylpentanoate 
• 14371-10-9 (E)-3-phenylpropenal 
• 136290-37-4 1-((E)-1-Ethoxy-3-phenyl-allyl)-1H-[1,2,4]triazole 
• 55164-19-7 ethyl-(Z)-3-chloro-3-phenyl-2-propenoate 
• 104290-63-3 Z-4-chloro-4-methyl-3-phenyl-pent-2-enoic acid 
• 4460-46-2 3-chloro-3-phenyl-3H-diazirine 
• 104290-61-1 2-Chloro-3,3-dimethyl-2-phenyl-cyclopropanecarboxylic acid methyl ester 
• 99376-68-8 3,3-dimethyl-2-phenyl-cyclopropenecarboxylic acid 
• 62751-30-8 (E)-ethyl 4-methyl-3-phenylpent-2-enoate 
• 56146-87-3 N-isopropyl-3-phenylpropanamidate 
• 30828-19-4 ketene diisopropyl acetal 
• 104290-65-5 (E)-4-Hydroxy-4-methyl-3-phenyl-pent-2-enoic acid 

Downstream Products

• 61751-36-8 2,2-Dimethyl-3-phenyl-cyclopropan-carbonsaeure-⁽¹⁾-ethylester 
• 61751-36-8 (±)-trans-ethyl 2,2-dimethyl-3-phenylcyclopropanecarboxylate 
• 13133-97-6 2-methyl-3-phenylpentane-2,5-diol 
• 13133-99-8 4-methyl-3-phenylpent-3-en-1-ol 

Relevant articles and documents

Benzotriazole- and 1,2,4-triazole-stabilized allylic anions: Applications in syntheses of functionalized α,β-unsaturated ketones, γ-lactones, γ-lactams, and β-substituted esters

Deprotonated 1-(benzotriazol-1-yl)-1-ethoxy-2-hexene (7) reacted with alkyl halides, aldehydes, ketones, imines, and α,β-unsaturated esters to give exclusively the α-alkylated products 8a-c, 10a,b, 12, 14, 16, and 18a,b, respectively. Without isolation, these products were hydrolyzed under mild conditions to generate the corresponding simple or functionalized α,β-unsaturated ketenes 9a-c, 11a,b, 13, 15, 17, and 19a,b. Similar reactions with the phenyl-substituted analog 3-(benzotriazol-1-yl)-3-ethoxy-1-phenyl-1-propene (21) also gave the analogous α-products, but they were accompanied by small amounts of the γ-products in most cases. By contrast, deprotonation of the corresponding triazole derivative 29 with butyllithium followed by reactions with alkyl halides, aldehydes, ketones, or imines yielded exclusively γ-alkylated adducts 32, 34, 36, 38, 40, and 42. Intermediates 32, 34, 36, 38, 40, and 42 were readily converted into β-substituted esters 33a-c, γ-lactones 35a,b, 39, 41, and 43, and γ-lactams 37a-c on hydrolysis.

Synthetic applications of the β-lithiation of β-Aryl secondary amides: Diastereoselective and enantioselective substitutions

The sequence of β-lithiation and electrophilic substitution of β-aryl secondary amides is reported. The lithiations occur regioselectively at the β-position, and the resulting lithiated intermediates can be reacted with a wide range of electrophiles to give substituted products. Reactions of β-lithiated amides bearing an α-substituent provide substituted products with high diastereoselectivity. Electrophilic substitutions of β-lithiated N-methylamides in the presence of the chiral diamine (-)-sparteine provide highly enantioenriched products. The methodology is used to synthesize enantioenriched β-aryl β-substituted amides, acids, and lactones.

Improved enantioselection for chiral dirhodium(II) carboxamide-catalysed carbon-hydrogen insertion reactions of tertiary alkyl diazoacetates

Enantiocontrol in C-H insertion reactions of 3° alkyl diazoacetates, which is highly dependent on the catalyst ligand, is greatly enhanced with the use of dirhodium(II) tetrakis[methyl 1-acetylimidazolidin-2-one-4(S)-carboxylate), Rh2(4S-MACIM)4.

AMBERLYST-15 PROMOTED SYNTHESIS OF FUSED AND SPIRO γ-BUTYROLACTONES FROM β-HYDROXYESTERS

β-hydroxy esters have been converted into fused and spiro γ-butyrolactones in 50-90percent yield by refluxing with Amberlyst-15 resin in hydrocarbon solvent.Fused-ring lactones are formed with the cis geometry at the ring junction and the regiochemistry of the closure is that expected from a process proceeding through the most stabilized carbocation.The use of an acidic resin offers several advantages over standard aqueous acid conditions: (1) easier monitoring of the reaction, (2) convenient workup, and (3) higher yields.

RING OPENING AND RING ENLARGEMENT OF A CYCLOPROPENE CARBOXYLIC ACID

3,3-Dimethyl-2-phenyl-cyclopropenecarboxylic acid 4 is prepared, starting with chlorophenyldiazirine 1.With acids 4 yields the open chain carboxylic acids 5, 6 and 7.Thionylchloride leads to the cyclobutenone 10, DCC to the acid anhydrides 11 and 13.

Stereochemistry of the Reaction of Diorganocuprate(I) Complexes Derived from Grignard Reagents with α,β-Acetylenic Esters

Diorganocuprate(I) complexes RCH3CuMgX, prepared from methylcopper and Grignard reagents (i-PrMgBr and t-BuMgCl) gave mainly cis-1,4-addition of the alkyl group originally present in the Grignard reagents and small amounts of cis- and trans-1,4-addition of the methyl group introduced by methylcopper, when they were allowed to react with ethyl propiolate and ethyl phenylpropiolate.The proportion of cis-1,4-addition products did not change when the reaction temperature was raised from -78 deg C to room temperature.The configurations of the main reaction products from the reaction with ethyl phenylpropiolate, ethyl (Z)-β-isopropylcinnamate and ethyl (Z)-β-t-butylcinnamate, were established by conversion of the corresponding acids to β-isopropylindenone and β-t-butylindenone.