182316-07-0

Basic information

• Product Name: (1R,2S,6S,9R)-8-aza-7,11-dioxa-9-phenyltricyclo[6.4.0.0^2,6]dodecan-12-one
• Synonyms: (1R,2S,6S,9R)-8-aza-7,11-dioxa-9-phenyltricyclo[6.4.0.0^2,6]dodecan-12-one
• CAS NO: 182316-07-0
• Molecular Weight: 259.305
• Mol File: 182316-07-0.mol

Chemical Properties

• CAS DataBase Reference: (1R,2S,6S,9R)-8-aza-7,11-dioxa-9-phenyltricyclo[6.4.0.0^2,6]dodecan-12-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,6S,9R)-8-aza-7,11-dioxa-9-phenyltricyclo[6.4.0.0^2,6]dodecan-12-one(182316-07-0)
• EPA Substance Registry System: (1R,2S,6S,9R)-8-aza-7,11-dioxa-9-phenyltricyclo[6.4.0.0^2,6]dodecan-12-one(182316-07-0)

Safety Data

• Hazardous Substances Data: 182316-07-0(Hazardous Substances Data)

Upstream product

• 142-29-0 cyclopentene 
• 182316-01-4 (5R)-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one-N-oxide 
• 56613-80-0 D-2-phenylglycinol 
• 154902-54-2 (E)-(R)-N-(2-hydroxy-1-phenylethyl)-1-(4-methoxyphenyl)-methylideneamine 
• 321174-47-4 (R)-α-(hydroxymethyl)benzylhydroxylamine 
• 121269-45-2 (R)-5-phenyl-3,4,5,6-tetrahydro-2H-1,4-oxazin-2-one 

Relevant articles and documents

Design, synthesis, and 1,3-dipolar cycloaddition of (5R)- [and (5S)]-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one N-oxides as chiral (E)-geometry-fixed α-alkoxycarbonylnitrones

Optically pure (5R)- [and (5S)]-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one N-oxides [(5R)- and (5S)-2] were designed as chiral (E)-geometry-fixed α-alkoxycarbonylnitrones 1. The nitrones (5R)- and (5S)-2 were synthesized by three-step oxidation of (R)- and (S)-phenylglycinols [(R)- and (S)-3], condensation of the resulting (R)- and (S)-2-hydroxylamino-2-phenylethanols [(R)- and (S)-5] with glyoxylic acid, and cyclization of the intermediary nitrones (R)- and (S)-6b. The nitrone (5R)-2 reacted with olefins 7-14 under mild conditions to afford the corresponding cycloadducts 15-22 as the main products via the least sterically demanding exo modes. Cycloadduct 30 obtained from (5S)-2 and cyclopentadiene was effectively elaborated to (1S,4S,5R)-4-benzyloxycarbonylamino-2-oxabicyclo[3.3.0]oct-7-en-3-one (28), the key synthetic intermediate of carbocyclic polyoxin C.

Preparation and evaluation of a cyclic acyl nitrone as a synthon for stereospecific α-amino acid synthesis

The preparation and characterization of cyclic optically active (5R)- 3,4,5,6-tetrahydro-5-phenyl-2H-1,4-oxazin-2-one-N-oxide (2) is described. This nitrone, which is viewed as a template for the synthesis of γ- oxygenated α-amino acids, reacts with alkenes efficiently and with high stereospecificity.

Intermolecular 1,3-dipolar cycloaddition of chiral and geometry fixed α-alkoxycarbonylnitrone, 5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one N-oxide

The 1,3-dipolar cycloaddition of (R)-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one N-oxide[(5R)-2], a chiral and geometry fixed α-alkoxycarbonylnitrone, with alkenes 3-6 proceeded smoothly to afford cycloadducts 7-10 as main products via β-exo mode.