53380-21-5

Basic information

• Product Name: GAMMA-ETHYL-GAMMA-PHENYL-BUTYROLACTONE
• Synonyms: GAMMA-ETHYL-GAMMA-PHENYL-BUTYROLACTONE
• CAS NO: 53380-21-5
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.2384
• Mol File: 53380-21-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 333.8°Cat760mmHg
• Flash Point: 138.2°C
• Appearance: /
• Density: 1.078g/cm³
• Vapor Pressure: 0.000134mmHg at 25°C
• Refractive Index: 1.522
• CAS DataBase Reference: GAMMA-ETHYL-GAMMA-PHENYL-BUTYROLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: GAMMA-ETHYL-GAMMA-PHENYL-BUTYROLACTONE(53380-21-5)
• EPA Substance Registry System: GAMMA-ETHYL-GAMMA-PHENYL-BUTYROLACTONE(53380-21-5)

Safety Data

• Hazardous Substances Data: 53380-21-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H14O2/c1-2-12(9-8-11(13)14-12)10-6-4-3-5-7-10/h3-7H,2,8-9H2,1H3

Upstream product

• 6270-17-3 ethyl 3-benzoylpropanoate 
• 925-90-6 ethylmagnesium bromide 
• 93-55-0 1-phenyl-propan-1-one 
• 123-25-1 succinic acid diethyl ester 
• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 33553-82-1 4-chloro-1-phenyl-1-butanol 
• 17720-64-8 N-acetoxyphthalimide 
• 5747-06-8 4-phenylpent-4-enoic acid 
• 2039-93-2 1-ethylstyrene 
• 75-05-8 acetonitrile 
• 2051-95-8 succinylbenzene 
• 187600-79-9 (1S,2R)-N-methylephedrinyl acrylate 
• 52253-57-3 (1R,2S)-N-methylephedrinyl acrylate 

Downstream Products

• 25607-04-9 4-Phenyl-4-methyl-hexancarbonsaeure 
• 5354-04-1 4-phenylhexanoic acid 

Relevant articles and documents

Enantioselective Bromolactonization of Trisubstituted Olefinic Acids Catalyzed by Chiral Pyridyl Phosphoramides

Enantioselective bromolactonization of trisubstituted olefinic acids producing synthetically useful chiral lactones with two contiguous asymmetric centers has remained mainly unexplored except for the 6-exo cyclization mode. In this work, the 5-exo- and 6

Electroreductive coupling of aromatic ketones, aldehydes, and aldimines with α,β-unsaturated esters: Synthesis of 5-aryl substituted γ-butyrolactones and lactams

The electroreductive intermolecular coupling of aromatic ketones and aldehydes with α,β-unsaturated esters in the presence of TMSCl gave the adducts as γ-trimethylsiloxy esters. The detrimethylsilylation of the adducts with TBAF afforded 5-aryl substituted γ-butyrolactones. The electroreductive coupling of N-(4-methoxyphenyl)-1-arylmethaneimines with methyl acrylate in the presence of TMSCl gave the adducts as methyl 4-aryl-4-((4-methoxyphenyl)amino)butanoates. The adducts were transformed to 5-aryl-γ-butyrolactams by cyclization with NaH and subsequent oxidation with CAN. (±)-Norcotinine was prepared from nicotinaldehyde by this method. The electroreductive coupling of aromatic ketones and aldimines with acrylonitrile in the presence of TMSCl gave 4-aryl-4-(trimethylsiloxy)butanenitriles and 4-aryl-4-((4-methoxyphenyl)amino)butanenitriles, respectively.

Gated access to α-lithiated phenyltetrahydrofuran: Functionalisation via direct lithiation of the parent oxygen heterocycle

Cycloreversion of α-lithiated phenyltetrahydrofuran was successfully tamed at -78 °C in a non-coordinating solvent in the presence of TMEDA. This anion showed excellent nucleophilicity and could be intercepted with a variety of structurally different electrophiles to give 2,2-disubstituted derivatives which can be further elaborated to γ-butyrolactones. The Royal Society of Chemistry 2013.