21939-14-0

Basic information

• Product Name: (8aR*,11aS*,11bR*)-10-phenyl-5,8a,11a,11b-tetrahydropyrrolo[3′,4′:4,5][1,2]oxazolo[3,2-a]isoquinoline-9,11(6H,10H)-dione
• CAS NO: 21939-14-0
• Molecular Weight: 320.348
• Mol File: 21939-14-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (8aR*,11aS*,11bR*)-10-phenyl-5,8a,11a,11b-tetrahydropyrrolo[3′,4′:4,5][1,2]oxazolo[3,2-a]isoquinoline-9,11(6H,10H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (8aR*,11aS*,11bR*)-10-phenyl-5,8a,11a,11b-tetrahydropyrrolo[3′,4′:4,5][1,2]oxazolo[3,2-a]isoquinoline-9,11(6H,10H)-dione(21939-14-0)
• EPA Substance Registry System: (8aR*,11aS*,11bR*)-10-phenyl-5,8a,11a,11b-tetrahydropyrrolo[3′,4′:4,5][1,2]oxazolo[3,2-a]isoquinoline-9,11(6H,10H)-dione(21939-14-0)

Safety Data

• Hazardous Substances Data: 21939-14-0(Hazardous Substances Data)

Upstream product

• 941-69-5 N-phenyl-maleimide 
• 22901-09-3 2-(2-bromoethyl)benzaldehyde 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 83-25-0 N-phenylmaleimide 
• 24423-87-8 3,4-dihydro-isoquinoline 2-oxide 

Relevant articles and documents

Metal-Free Solvent Promoted Oxidation of Benzylic Secondary Amines to Nitrones with H2O2

An environmentally benign protocol for the generation of nitrones from benzylic secondary amines via catalyst-free oxidation of secondary amines using H2O2 in MeOH or CH3CN is described. This methodology provides a selective access to a variety of C-aryl nitrones in yields of 60 to 93%. Several studies have been performed to shed light on the reaction mechanism and the role of the solvent.

STERIC EFFECTS VS SECONDARY ORBITAL INTERACTIONS IN NITRONE CYCLOADDITIONS. STERIC EFFECTS IN CYCLOREVERSIONS OF ISOXAZOLIDINES.

3,4-Dihydroisoquinoline-N-oxide 1 reacted readily with both acyclic (Z)- and (E)-disubstituted alkenes bearing electron-attracting substituents (methoxycarbonyl, cyano, phenylsulphonyl and benzoyl groups) and with cyclic derivatives (e.g.) maleimides) to give mixtures of the two possible diastereoisomers.Similar amounts of endo- and exo-adducts were formed in the reactions of (Z)-cyano, methoxycarbonyl and benzoyl derivatives whereas exo-addition clearly won over its endo-counterpart in the case of (Z)-(phenylsulphonyl) and cyclic derivatives.High exo-selectivity was also observed in the sluggish reactions of 1 with electron-rich alkenes .Our results, which revise previous literature data, clearly show that an "endo-rule" does not hold for the reactions of 1 with (Z)-1,2-disubstituted alkenes.We conclude that in these reactions repulsive steric interactions either counteract efficiently or clearly win over stabilizing secondary orbital overlaps in controlling endo/exo-selectivity.These reactions were found reversible under mild conditions so that relative formation rates of related pairs of (Z)- and (E)-dipolarophiles in cycloreversion processes of isoxazolidines could be determined; as a rule (E)-alkenes are extruded faster than (Z)-isomers.These results provide unambiguous experimental evidence that increase in steric compression between the substituents in (Z)-alkenes, on their way toward transition state, is not a major factor in determining their lower reactivity with respect to (E)-isomers in 1,3-dipolar cycloadditions.