53380-21-5

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 
• 52253-57-3 (1R,2S)-N-methylephedrinyl acrylate 
• 187600-79-9 (1S,2R)-N-methylephedrinyl acrylate 
• 17720-64-8 N-acetoxyphthalimide 
• 5747-06-8 4-phenylpent-4-enoic acid 
• 2039-93-2 1-ethylstyrene 
• 75-05-8 acetonitrile 
• 33553-82-1 4-chloro-1-phenyl-1-butanol 
• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 2051-95-8 succinylbenzene 

Downstream Products

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

Relevant academic research and scientific papers

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

Access to Alkyl-Substituted Lactone via Photoredox-Catalyzed Alkylation/Lactonization of Unsaturated Carboxylic Acids

An efficient photoredox-catalyzed alkylation/lactonization reaction of unsaturated carboxylic acids by using alkyl N-hydroxyphthalimide esters as alkylation reagents has been developed. Varieties of redox-active esters derived from aliphatic carboxylic acids were proved viable in this method, affording alkyl substituted lactones in moderate to good yields. This redox-neutral procedure features mild conditions and operational simplicity, which provides a new strategy for the synthesis of alkyl substituted lactones.

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.

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.

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.