85416-75-7

Basic information

• Product Name: (4S)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE
• Synonyms: (4R)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE;(4S)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE;(S)-(+)-ROLIPRAM;(R)-(-)-ROLIPRAM;(4R)-4-(3-(Cyclopentyloxy)-4-methoxyphenyl)pyrrolidine-2-one;Rolipram (R)-(-)-;(4R)-(3-(Cyclopentyloxy)-4-methoxyphenyl)pyrrolidin-2-one;4-[3-(cyclopentoxy)-4-methoxy-phenyl]-2-pyrrolidone
• CAS NO: 85416-75-7
• Molecular Formula: C₁₆H₂₁NO₃
• Molecular Weight: 275.34
• Product Categories: Cyclic Nucleotide related;Signalling
• Mol File: 85416-75-7.mol
• Article Data: 34

Chemical Properties

• Melting Point: 132.0 to 136.0 °C
• Boiling Point: 472.7 °C at 760 mmHg
• Flash Point: 239.7 °C
• Appearance: /
• Density: 1.155 g/cm³
• Storage Temp.: Store at RT
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 16.02±0.40(Predicted)
• CAS DataBase Reference: (4S)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE(85416-75-7)
• EPA Substance Registry System: (4S)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE(85416-75-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 85416-75-7(Hazardous Substances Data)

Usage

Uses

R-(-)-Rolipram is a phosphodiesterase IV (PDE4) inhibitor and anti-inflammatory agent with some antidepressant activity. It is the R isomer of (±)-Rolipram (R640040). Potent PDE4 inhibitor.

Biological Activity

More active enantiomer of the PDE4 inhibitor rolipram (4-(3-(Cyclopentyloxy)-4-methoxyphenyl)pyrrolidin-2-one ); 2-10-fold more potent than the S-(+) enantiomer ((4S)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one ). Also available as part of the Phosphodiesterase Inhibitor Tocriset? .

Upstream product

• 61413-54-5 Rolipram 
• 1402406-47-6 (R)-2-(cyclopentyloxy)-1-methoxy-4-(1-nitrobut-3-en-2-yl)benzene 
• 1402406-56-7 (R)-3-(3-(cyclopentyloxy)-4-methoxyphenyl)-4-nitrobutan-1-ol 
• 146426-63-3 (+/-)-1-Benzyl-4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidin-2-one 
• 256399-08-3 N-{4-[4-(3-cyclopentyloxy-4-methoxy-phenyl)-2-oxo-pyrrolidin-1-yl]-phenyl}-acetamide 
• 191610-56-7 (2S,3R)-1-tert-butoxycarbonyl-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-oxopyrrolidine-2-carboxylic acid 
• 175165-67-0 (R)-4-Azido-3-(3-cyclopentyloxy-4-methoxy-phenyl)-butyric acid methyl ester 
• 141099-45-8 4-Amino-3-(3-cyclopentyloxy-4-methoxy-phenyl)-butyric acid methyl ester 
• 145548-98-7 (3S,7R,7aR)-7-(3-Cyclopentyloxy-4-methoxy-phenyl)-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 
• 145548-99-8 (4R,5R)-4-(3-Cyclopentyloxy-4-methoxy-phenyl)-5-hydroxy-pyrrolidin-2-one 
• 137-43-9 Cyclopentyl bromide 
• 132683-32-0 (R)-4-(3-hydroxy-4-methoxyphenyl)pyrrolidin-2-one 

Downstream Products

• 686712-07-2 3-[4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxopyrrolidin-1-yl]benzonitrile 
• 1295626-70-8 (R)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-methylpyrrolidin-2-one 
• 686712-10-7 4-[4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxopyrrolidin-1-yl]benzenesulfonamide 
• 132683-32-0 (R)-4-(3-hydroxy-4-methoxyphenyl)pyrrolidin-2-one 

Relevant articles and documents

Polysulfonate supported chiral diamine-nickel catalysts: Synthesis and applications

A series of chiral polysulfonate cyclohexyldiamine-Ni(II) catalysts were prepared via sulfur (VI) fluoride exchange click-reactions. The catalysts exhibited good catalytic activity and enantioselectivity in the Michael addition of malonates to nitroalkene

Enantioselective conjugate addition of an α,α-dithioacetonitrile with nitroalkenes using chiral bis(imidazoline)-Pd complexes

The enantioselective conjugate addition reaction of an α,α-dithioacetonitrile with nitroalkenes was catalysed by chiral bis(imidazoline)-palladium pincer-type complexes. The reaction was applicable to various nitroalkenes to afford products in good yield with high enantioselectivity. The obtained products can be converted to γ-lactam and biologically active rolipram.

Highly Enantioselective Synthesis of Chiral γ-Lactams by Rh-Catalyzed Asymmetric Hydrogenation

A Rh/bisphosphine-thiourea (ZhaoPhos) catalytic system has been identified for the straightforward asymmetric synthesis of chiral γ-lactams. A variety of NH free α,β-unsaturated lactams bearing a β-aryl or β-alkyl substituent were smoothly hydrogenated to