120779-58-0

Basic information

• Product Name: 3(S)3a(S)6(R)6a(R)-2,3-diphenyl-6-menthyloxy-3,3a,6,6a-tetrahydro-4H-furo<3,4-d>isoxazol-4-one
• CAS NO: 120779-58-0
• Molecular Weight: 435.563
• Mol File: 120779-58-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3(S)3a(S)6(R)6a(R)-2,3-diphenyl-6-menthyloxy-3,3a,6,6a-tetrahydro-4H-furo<3,4-d>isoxazol-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3(S)3a(S)6(R)6a(R)-2,3-diphenyl-6-menthyloxy-3,3a,6,6a-tetrahydro-4H-furo<3,4-d>isoxazol-4-one(120779-58-0)
• EPA Substance Registry System: 3(S)3a(S)6(R)6a(R)-2,3-diphenyl-6-menthyloxy-3,3a,6,6a-tetrahydro-4H-furo<3,4-d>isoxazol-4-one(120779-58-0)

Safety Data

• Hazardous Substances Data: 120779-58-0(Hazardous Substances Data)

Upstream product

• 112968-75-9 (5R)-(L-menthyloxy)-2(5H)-furanone 
• 201024-81-9 C,N-diphenylnitrone 
• 1137-96-8 (Z)-N-benzylideneaniline oxide 

Relevant articles and documents

Asymmetric 1,3-dipolar cycloadditions to 5-(R)-menthyloxy-2(5H)-furanone

Various diazo compounds, nitrile oxides, nitrones and azomethine ylides were examined in 1,3-dipolar cycloadditions to enantiomerically pure 5-(R)-menthyloxy-2(5H)-furanone 1a. Pyrazoline 9 was obtained in 100% c.y. as a mixture of 2 diastereoisomers in ratios up to 72:28, whereas pyrazoline 16 was obtained in 100% c.y. as a single enantiomer. Photochemically pyrazolines 9 and 10 have been converted to cyclopropanes 11 and 13. Under thermal conditions pyrazoline 9 is converted to 4-methyl-5-menthyloxy-2(5H)-furanone. Isoxazoles 21a-24a were obtained enantiomerically pure via nitrile oxide addition to 1a in 64-67% yield. Nitrone addition afforded isoxazolidines 27, 28 and 34 with complete anti-facial- and regiochemistry, but with endo-exo-selectivities up to 76%. Enantiomerically pure isoxazolidines were obtained in 25-75% yield. Pyrrolidine 36 was obtained diastereomerically pure in 81% c.y. Pyrrolidines 42 and 45, however, were obtained as diastereomeric mixtures in 37% resp. 6% yield.