109905-95-5

Basic information

• Product Name: (3R,4S,5S)-3-hydroxy-5-[(R)-hydroxy-phenyl-methyl]-1-methyl-4-phenyl-p yrrolidin-2-one
• Synonyms: 2-Pyrrolidinone, 3-hydroxy-5-[(R)-hydroxyphenylmethyl]-1-methyl-4-phenyl-, (3R,4S,5S)-
• CAS NO: 109905-95-5
• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.35
• Mol File: 109905-95-5.mol

Chemical Properties

• Boiling Point: 531.7°Cat760mmHg
• Flash Point: 275.3°C
• Appearance: /
• Density: 1.27g/cm³
• CAS DataBase Reference: (3R,4S,5S)-3-hydroxy-5-[(R)-hydroxy-phenyl-methyl]-1-methyl-4-phenyl-p yrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,5S)-3-hydroxy-5-[(R)-hydroxy-phenyl-methyl]-1-methyl-4-phenyl-p yrrolidin-2-one(109905-95-5)
• EPA Substance Registry System: (3R,4S,5S)-3-hydroxy-5-[(R)-hydroxy-phenyl-methyl]-1-methyl-4-phenyl-p yrrolidin-2-one(109905-95-5)

Safety Data

• Hazardous Substances Data: 109905-95-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3R,4S,5S)-3-hydroxy-5-[(R)-hydroxy-phenyl-methyl]-1-methyl-4-phenyl-pyrrolidin-2-one is used as a potential pharmaceutical agent for its possible biological activities. The unique arrangement of functional groups and its optical activity may contribute to its efficacy in targeting specific biological pathways or receptors, making it a candidate for the development of new drugs.
Used in Research and Development:
In the field of organic chemistry and medicinal chemistry, (3R,4S,5S)-3-hydroxy-5-[(R)-hydroxy-phenyl-methyl]-1-methyl-4-phenyl-pyrrolidin-2-one serves as a valuable compound for research and development. Its complex structure and stereochemistry make it an interesting subject for studying the relationship between molecular structure and biological activity, potentially leading to the discovery of novel therapeutic agents or a better understanding of molecular interactions.

InChI:InChI=1/C18H19NO3/c1-19-15(16(20)13-10-6-3-7-11-13)14(17(21)18(19)22)12-8-4-2-5-9-12/h2-11,14-17,20-21H,1H3/t14-,15-,16+,17+/m0/s1

Upstream product

• 109838-82-6 (+/-)-(4R^*,5R^*)-5-formyl-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-81-5 (+/-)-(4R^*,5R^*)-5-(hydroxymethyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-84-8 (+/-)-(4R^*,5R^*)-5-benzoyl-1-methyl-4-phenylpyrrolidin-2-one 
• 4192-77-2 ethyl cinnamate 
• 103541-15-7 (+/-)-clausenamide 
• 132490-26-7 (2R,3S)-phenyl 3-phenyloxirane-2-carboxylate 
• 130202-78-7 (2R,3S)-N-methyl-N-(β-hydroxyphenylethyl)-3-phenyl-2,3-epoxypropionamide 
• 130202-79-8 (2R,3S)-2,3-Epoxy-N-methyl-N-phenacyl-3-phenylpropionamide 
• 5411-12-1 trans-(2S,3R)-epoxy-1,3-diphenylpropan-1-one 
• 109905-94-4 (+)-(4S,5S,7R)-5-(α-hydroxybenzyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-83-7 (+/-)-(4R^*,5R^*,7R^*)-5-(α-hydroxybenzyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-79-1 (+/-)-(4R^*,5R^*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-77-9 5,5-Diethoxycarbonyl-1-methyl-4-phenyl-pyrrolidin-2-one 
• 109838-78-0 (2S,3R)-1-Methyl-5-oxo-3-phenyl-pyrrolidine-2,2-dicarboxylic acid ethyl ester 

Relevant articles and documents

High performance liquid chromatographic separation of clausenamide enantiomers with chiral-AGP stationary phase

A method of high performance liquid chromatographic separation of clausenamide enantiomers with chiral-AGP (α1-acid glycoprotein) stationary phases has been established. The absolute configurations of (-)clausenamide and (+)clausenamide are 3S, 4R, 5R, 6S and 3R, 4S, 5S, 6R, respectively. The present method has been used to analyze the (-)clausenamide and (+)clausenamide and its analogues such as the major metabolite and synthetic derivatives of clausenamide.

Synthesis and activity in enhancing long-term potentiation (LTP) of clausenamide stereoisomers

Clausenamide, isolated from aqueous extract of dry leaves of Clausena lansium, a Chinese folk medicine, was found to have potent activity in enhancing LTP and show nootropic activity in animal tests. In order to discovery more potent stereoisomers and to

Highly efficient and concise synthesis of both antipodes of SB204900, clausenamide, neoclausenamide, homoclausenamide and ζ-clausenamide. Implication of biosynthetic pathways of clausena alkaloids

The synthesis of both antipodes of N-methyl-N-[(Z)-styryl]-3-phenyloxirane- 2-carboxamide (SB204900), clausenamide, neoclausenamide, homoclausenamide and ζ-clausenamide have been accomplished using (2S,3R)- and (2R,3S)-3-phenyloxirane-2-carboxamides as the starting materials, and SB204900 was found to be a common precursor to other N-heterocyclic clausena alkaloids. Mediated by Bronsted acids under different conditions, for example, SB204900 underwent efficient and diverse alkene-epoxide cyclization, enamide-epoxide cyclization and arene-epoxide cyclization reactions to produce the five-membered N-heterocyclic neoclausenamide, its 6-epimer, the six-membered N-heterocyclic homoclausenamide and the eight-membered N-heterocyclic ζ-clausenamide, respectively, in good to excellent yields. Regiospecific oxidation of neoclausenamide and its 6-epimer afforded neoclausenamidone. Enolization of neoclausenamidone in the presence of LiOH and the subsequent protonation under kinetic conditions at -78 °C led to the epimerization of neoclausenamidone into clausenamidone. Reduction of clausenamidone using NaBH4 furnished clausenamide in high yield. The Royal Society of Chemistry 2009.

New procedures for the Julia-Colonna asymmetric epoxidation: Synthesis of (+)-clausenamide

The oxidation of chalcone 1 to optically active epoxide 2 [a precursor of (+)-clausenamide (+)-3] may be effected using a 15-mer or 20-mer of L-leucine bound to a PEG based support; poly-L-leucines of this type may be used as immobilised catalysts in a fixed-bed reactor.

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.