103541-15-7

Basic information

• Product Name: Clausenamide
• Synonyms: (-)-3-hydroxy-5-(hydroxy-phenyl-methyl)-1-methyl-4-phenyl-pyrrolidin-2-one;(-)Clausenamide;levoclausenamide;(3R,4S,5S)-3-Hydroxy-5-[(R)-hydroxy-phenylmethyl]-1-methyl-4-phenylpyrrolidin-2-one;(3R)-1-Methyl-3α-hydroxy-4β-phenyl-5β-[(R)-α-hydroxybenzyl]pyrrolidine-2-one;(3R)-3α-(Hydroxy)-5β-[(R)-hydroxy(phenyl)methyl]-1-methyl-4β-phenylpyrrolidin-2-one
• CAS NO: 103541-15-7
• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.34836
• Mol File: 103541-15-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 531.7 °C at 760 mmHg
• Flash Point: 275.3 °C
• Appearance: /
• Density: 1.27 g/cm³
• Vapor Pressure: 3.91E-12mmHg at 25°C
• Refractive Index: 1.633
• PKA: 12.93±0.60(Predicted)
• CAS DataBase Reference: Clausenamide(CAS DataBase Reference)
• NIST Chemistry Reference: Clausenamide(103541-15-7)
• EPA Substance Registry System: Clausenamide(103541-15-7)

Safety Data

• Hazardous Substances Data: 103541-15-7(Hazardous Substances Data)

Usage

General Description

Clausenamide is a naturally occurring chemical compound found in the plant Clausena lansium, also known as Wampee. It has been identified as a bioactive substance with potential pharmacological properties, including anti-inflammatory and antitumor activities. Clausenamide has also demonstrated inhibitory effects on the growth of cancer cells in laboratory studies. Its potential for use in the development of novel medicinal drugs and as a natural source of therapeutic compounds warrants further investigation and research.

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

• 109838-83-7 (+/-)-(4R^*,5R^*,7S^*)-5-(α-hydroxybenzyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 4192-77-2 ethyl cinnamate 
• 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 
• 109838-84-8 (+/-)-(4R^*,5R^*)-5-benzoyl-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-81-5 (+/-)-(4R^*,5R^*)-5-(hydroxymethyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-82-6 (+/-)-(4R^*,5R^*)-5-formyl-1-methyl-4-phenylpyrrolidin-2-one 
• 13992-75-1 5,5-Diethoxycarbonyl-4-phenylpyrrolidin-2-one 

Downstream Products

• 109905-95-5 (±)-(3R,4S,5S,6R)-clausenamide 

Relevant articles and documents

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.