138291-10-8

Basic information

• Product Name: (-)-8-Phenylmenthyl (R)-2-phenylpropionate
• Synonyms: (-)-8-Phenylmenthyl (R)-2-phenylpropionate
• CAS NO: 138291-10-8
• Molecular Weight: 364.528
• Mol File: 138291-10-8.mol

Chemical Properties

• CAS DataBase Reference: (-)-8-Phenylmenthyl (R)-2-phenylpropionate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-8-Phenylmenthyl (R)-2-phenylpropionate(138291-10-8)
• EPA Substance Registry System: (-)-8-Phenylmenthyl (R)-2-phenylpropionate(138291-10-8)

Safety Data

• Hazardous Substances Data: 138291-10-8(Hazardous Substances Data)

Upstream product

• 77-78-1 dimethyl sulfate 
• 156208-22-9 8-Phenylmenthyl phenylacetate 
• 88002-15-7 Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester 
• 591-51-5 phenyllithium 
• 88292-44-8 (1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (S)-2-hydroxy-2-phenylpropanoate 
• 88292-45-9 (1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-2-hydroxy-2-phenylpropanoate 
• 88292-41-5 2-Oxopropansaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>ester 
• 65253-04-5 (-)-8-phenylmenthol 
• 103-82-2 phenylacetic acid 
• 74-88-4 methyl iodide 
• 138291-08-4 (R)-2-Methylsulfanylthiocarboxyoxy-2-phenyl-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 138291-07-3 (S)-2-Methylsulfanylthiocarboxyoxy-2-phenyl-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Downstream Products

• 1123-85-9 (+)-(R)-2-phenylpropanol 
• 65253-04-5 (-)-8-phenylmenthol 

Relevant articles and documents

Samarium diiodide-mediated asymmetric reactions of 8-phenylmenthyl esters

(-)-8-Phenylmenthol was used as a chiral auxiliary to direct asymmetric reactions of its preformed carboxylates. Reduction of xanthates 1a and 1b by SmI2 likely proceeded via HMPA-bound samarium enolate intermediates. Self- and cross-pinacolic

Diastereoselective Alkylation of 8-Phenylmenthyl Phenylacetate: Aggregated Lithium Enolate versus "Naked" Enolate

It is shown that monoalkylation of 8-phenylmenthyl phenylacetate using lithiated bases leads to poor or no diastereoselectivities (50/50 to 69/31) and high yields (75 to 98percent) while alkylation using tBu-P4 (a strong and cation free base, known to provide "naked" anion) leads to high diastereoselectivities (92/8 to 98/2) and high yields (65 to 95percent).It is postulated that, in the case of phenylacetates, the degree of aggregation of the lithium enolate is responsible of the poor diastereoselectivities.

Stereogenic Reactions of the α-Carbon Radicals of 8-Phenylmenthyl Esters

The stereoselective free-radical type reduction and cyclisation of 8-phenylmenthyl esters is described; the predominant products are considered to be derived from the transition states with conformations having the larger substituent anti to the alkoxy group of the ester.