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

• 80595-59-1 bromoacetic acid (-)-8-phenylmenthol ester 
• 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 
• 72526-00-2 (-)-8-phenylmenthyl acrylate 
• 75-52-5 nitromethane 
• 86253-91-0 di<(1R,2S,5R)-8-phenylmenthyl> fumarate 
• 79-08-3 bromoacetic acid 

Downstream Products

• 88196-09-2 (2R,3R)-2-Hydroxy-3-methyl-pent-4-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 88196-07-0 (-)-8-phenylmenthyl (2S,3S)-2-hydroxy-3-methyl-4-pentenoate 
• 108794-01-0 (-)-8-phenylmenthyl (2S)-2-hydroxy-4-pentenoate 
• 88112-35-0 (-)-8-phenylmenthyl (2S,3R)-2-hydroxy-3-methyl-4-pentenoate 
• 133392-31-1 (2R)-2-hydroxy-2-(2-hydroxy-5-methoxyphenyl)ethanoic acid (-)-8-phenylmenthyl ester 
• 133392-31-1 (2S)-2-hydroxy-2-(2-hydroxy-5-methoxyphenyl)ethanoic acid (-)-8-phenylmenthyl ester 
• 108794-06-5 (2'S)-3'-(cyclohex-1-enyl)-2'-hydroxy-propionic acid (1R,2S,5R)-8-phenylmenthyl ester 
• 108793-96-0 (-)-8-phenylmenthyl (2S)-2-hydroxy-2-(2-cyclohexenyl)acetate 
• 105229-98-9 (1R)-8-phenylmenthyl hydroxyacetate 
• 105229-97-8 (1R)-8-phenylmenthyl (2R)-2-hydroxy-6-methyl-6-heptenoate 
• 105229-96-7 (1R)-8-phenylmenthyl (2S)-2-hydroxy-6-methyl-6-heptenoate 
• 185515-94-0 <1R-(1α,2β,5α)>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-hydroxy-3-nitropropanoate 
• 502506-84-5 (1R,3R,4S)-8-phenylmenthyl (2S,3R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-hydroxy-4-methylpent-4-enoate 
• 161661-47-8 (-)-(1R,2S,5R)-8-phenylmenthyl (1S,3S,4R)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-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).

Highly stereoselective cycloadditions of Danishefsky's diene to (-)-8-phenylmenthyl and (+)-8-phenylneomenthyl glyoxylate N-phenylethylimines

Enantiopure 4-oxo-pipecolic acid derivatives were obtained by double asymmetric induction aza-Diels-Alder reactions between chiral glyoxylate N-phenylethylimines and Danishefsky's diene mediated by zinc iodide. The key to success was the use of iminoacetates possessing two chiral auxiliaries, N-(S)- or N-(R)-1-phenylethyl and (-)-8-phenylmenthyl or (+)-8-phenylneomenthyl. Adducts were formed in good yields (78-81%), with complete regioselectivity and high diastereoselectivity (87-96%). The absolute configuration of the adducts formed was unequivocally assigned through NMR, specific optical rotation and X-ray data of appropriated derivatives. These cycloadducts can serve as precursors for bioactive piperidinic azasugars and pipecolic acid derivatives.

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.