13992-75-1

Usage

InChI:InChI=1/C16H19NO5/c1-3-21-14(19)16(15(20)22-4-2)12(10-13(18)17-16)11-8-6-5-7-9-11/h5-9,12H,3-4,10H2,1-2H3,(H,17,18)

Upstream product

• 4192-77-2 ethyl cinnamate 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 103-36-6 ethyl 3-phenyl-2-propenoate 

Downstream Products

• 109838-77-9 5,5-Diethoxycarbonyl-1-methyl-4-phenyl-pyrrolidin-2-one 
• 124687-28-1 (+/-)-cis-5-carbethoxy-trans-5-carboxy-4-phenyl-2-pyrrolidinone 
• 14226-05-2 4-phenyl-5,5-dicarboxy-2-pyrrolidinone 
• 109838-79-1 (+/-)-(4R^*,5R^*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-79-1 (+/-)-(4R^*,5S^*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 1338928-99-6 C₂₀H₂₁NO₄ 
• 1338929-01-3 C₁₂H₁₅NO₃ 
• 1338929-00-2 C₁₂H₁₅NO₃ 
• 1338929-05-7 C₁₉H₂₁NO₃ 
• 1338929-04-6 C₁₉H₂₁NO₃ 
• 1338929-07-9 C₂₉H₂₉NO₆ 
• 1338929-06-8 C₂₉H₂₉NO₆ 
• 608128-73-0 (3R,4S,5S,6S)-epi-cis-clausenamide 
• 124687-29-2 (+/-)-cis-5-(hydroxymethyl)-4-phenyl-2-pyrrolidinone 

Relevant academic research and scientific papers

Preparation of 4- and 6-desphenyl analogues of (-)-clausenamide and alternative synthesis of (+)-epi-clausenamide

4- and 6-desphenyl analogues of (-)-clausenamide, 6 and 7, were prepared in optical active form from commercially available d-pyroglutamic acid and the known racemic pyrrolidinone 13, respectively. In order to confirm the absolute stereochemistry of (+)-

Selective Inhibition of γ-Aminobutyric Acid Aminotransferase by (3R,4R),(3S,4S)- and (3R,4S),(3S,4R)-4-Amino-5-fluoro-3-phenylpentanoic Acids

(3R,4R),(2S,4S)- and (3R,4S),(3S,4R)-4-amino-5-fluoro-3-phenylpentanoic acid (1a and 1b) were synthesized and studied as selective inactivators of γ-aminobutyric acid (GABA) aminotransferase.Neither compound caused time-dependent inactivation of the enzym

Process for the preparation of gamma-butyrolactams

A process for the preparation of a C(3)-C(4)-transconfigurated γ-butyrolactam of the formula (I) STR1 in which R1 represents hydrogen or alkyl, aryl or aralkyl with in each case up to 10 carbon atoms and R2 and R3 are iden

Process for the preparation of clausenamide

A new synthetic route to clausenamide having the formula STR1 has been found. It has been found that a compound of the formula STR2 can be oxidized to provide the stereochemically correctly configured product, clasuenamide. A number of new compounds usefu

Diastereoselective and Enantioselective Total Synthesis of the Hepatoprotective Agent Clausenamide

The diastereoselective total synthesis of the naturally ocurring hepatoprotective agent clausenamide (3-hydroxy-5-(α-hydroxybenzyl)-1-methyl-4-phenylpyrrolidin-2-one) is described, starting from ethyl cinnamate and diethyl acetamidomalonate.The enantioselective total synthesis of optically pure (+)-clausenamide is presented.The synthesis is based on a novel method for the preparation of optically pure (2S,3S)-3-phenylglutamic acid.

Hypolipidemic activity of substituted 2-pyrrolidinones in rodents

A series of substituted 2-pyrrolidinones was evaluated for hypolipidemic activity at 20 and 30 mg/kg/day in CF1 male mice. 4-Phenyl-5,5-dicarbethoxy-2-pyrrolidinone was the most potent compound at 30 mg/kg/day, reducing serum triglyceride levels 52% after 14 days of dosing and serum cholesterol levels 48% after 16 days of dosing. 4-Phenyl-5-carbethoxy-2-pyrrolidinone and 4-phenyl-3,5,5-tricarbethoxy-2-pyrrolidinone also demonstrated significant activity. Those compounds which contained a phenyl substituent were more potent than either the unsubstituted, the alkyl, or the dicarbethoxy 2-pyrrolidinone analogues.