84312-20-9

Basic information

• Product Name: Acetic acid, oxo-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
• CAS NO: 84312-20-9
• Molecular Formula: C18H24O3
• Molecular Weight: 288.387
• Mol File: 84312-20-9.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: Acetic acid, oxo-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, oxo-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester(84312-20-9)
• EPA Substance Registry System: Acetic acid, oxo-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester(84312-20-9)

Safety Data

• Hazardous Substances Data: 84312-20-9(Hazardous Substances Data)

Upstream product

• 75-52-5 nitromethane 
• 72526-00-2 (-)-8-phenylmenthyl acrylate 
• 1427281-83-1 (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate 
• 1427281-87-5 (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]piperidine-2-carboxylate 
• 71804-27-8 (1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate 
• 65253-04-5 (-)-8-phenylmenthol 
• 129180-87-6 (-)-8-phenylmenthol phenylcarbamate 
• 57707-91-2 (5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanol 
• 97371-54-5 (-)-(2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanon 
• 89-82-7 pulegone 
• 215321-43-0 Chloro-oxo-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 86253-91-0 di<(1R,2S,5R)-8-phenylmenthyl> fumarate 
• 79-08-3 bromoacetic acid 
• 80595-59-1 bromoacetic acid (-)-8-phenylmenthol ester 

Downstream Products

• 108794-01-0 (-)-8-phenylmenthyl (2S)-2-hydroxy-4-pentenoate 
• 108793-96-0 (-)-8-phenylmenthyl (2S)-2-hydroxy-2-(2-cyclohexenyl)acetate 
• 212073-01-3 (-)-(1R)-8-phenylmenthyl (1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-carboxylate 
• 1427281-87-5 (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]piperidine-2-carboxylate 
• 1427281-83-1 (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate 
• 1427281-85-3 (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate 
• 1431164-77-0 (-)-(1R,2S,5R)-8-phenylmenthyl (2R)-4-oxo-1-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate 

Relevant articles and documents

C- and N-Selective Grignard Addition Reactions of α-Aldimino Esters in the Presence or Absence of Zinc(II) Chloride: Synthetic Applications to Optically Active Azacycles

Highly practical synthetic methods were developed for the C- and N-selective Grignard addition reactions of N-4-MeOC6H4-protected α-aldimino esters in the presence or absence of zinc(II) chloride. Diastereoselective C-alkyl addition, tandem C-alkyl addition-N-alkylation, and some transformations to synthetically useful optically active azacycles were demonstrated. (Chemical Equation Presented).

The origin of stereoselectivity in cycloaddition reactions promoted by stereoisomers of 8-phenylmenthyl glyoxylate oxime

A structural study of three synthesized stereoisomeric oximes, (-)-8-phenylmenthyl glyoxylate oxime (8-PMGO), (+)-8-phenylneomenthyl glyoxylate oxime (8-PnMGO), and (-)-8-phenylisoneomenthyl glyoxylate oxime (8-PinMGO), was performed by means of variable temperature 1H NMR spectroscopy, X-ray crystallography, and ab initio calculations. It was found that in 8-PMGO a conformation where the phenyl and oxime moieties are stacked is significantly favored, whereas in the other stereoisomers this preference was not so evident. The conformational differences found between the isomers were used to rationalize the outcome of the reaction (simultaneous 1,3-cycloaddition and aza-Diels-Alder reaction) between the referred oximes and cyclopentadiene, in which the stereoselectivity was evaluated and found to be nicely reproduced by a simple conformational analysis. The global results indicate that the stereoselectivity of the studied oximes, a bit higher for 8-PMGO, originates from their particular conformational distribution, in which the phenyloxime aromatic interaction plays a decisive role.

The use of (-)-8-phenylisoneomenthol and (-)-8-phenylmenthol in the enantioselective synthesis of 3-functionalized 2-azabicyclo[2.2.1]heptane derivatives via aza-Diels-Alder reaction

The asymmetric aza-Diels-Alder reaction of the (1R)-8-phenylmenthyl or (1R)-8-phenylisoneomenthyl glyoxylate-derived N-benzylimine with cyclopentadiene resulted in the enantioselective synthesis of the corresponding pure [(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylates (80 or 69% yield, respectively). Reduction of these cycloadducts with LiAlH4 afforded pure (-)-[(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-yl]methanol. Furthermore, a reaction sequence based on Barbier-Wieland degradation of both (1S,3-exo)-adducts afforded pure (+)-(1R)-2-benzoyl-2-azabicyclo[2.2.1]heptan-3-one. In the course of the two transformation sequences referred, the chiral auxiliaries were recovered in a virtually quantitative way.