104870-80-6

Basic information

• Product Name: Cyclohexanol, 5-methyl-2-(1-methyl-1-phenylethyl)-, (1R,2R,5R)-
• CAS NO: 104870-80-6
• Molecular Formula: C16H24O
• Molecular Weight: 232.366
• Mol File: 104870-80-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Cyclohexanol, 5-methyl-2-(1-methyl-1-phenylethyl)-, (1R,2R,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanol, 5-methyl-2-(1-methyl-1-phenylethyl)-, (1R,2R,5R)-(104870-80-6)
• EPA Substance Registry System: Cyclohexanol, 5-methyl-2-(1-methyl-1-phenylethyl)-, (1R,2R,5R)-(104870-80-6)

Safety Data

• Hazardous Substances Data: 104870-80-6(Hazardous Substances Data)

Upstream product

• 5949-05-3 (S)-Citronellal 
• 98-09-9 benzenesulfonyl chloride 
• 144541-38-8 <1R-(1α,2α,5α)>-5-Methyl-2-(1-methylethenyl)cyclohexanol 
• 104870-79-3 (2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanone 
• 89-82-7 pulegone 
• 144375-66-6 4-Methoxy-1-[(1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxycarbonyl]-3-triisopropylsilanyl-pyridinium; chloride 
• 126378-43-6 (-)-8-phenylmenthol chloroformate 
• 126378-69-6 (R)-2-Isobutyl-4-oxo-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 67-56-1 methanol 
• 57707-91-2 (5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanol 
• 100-58-3 phenylmagnesium bromide 
• 205057-17-6 (5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanone 

Downstream Products

• 129180-91-2 1-(1-methyl-1-phenylethyl)-4-methylcyclohexene 
• 65253-04-5 (-)-8-phenylmenthol 
• 100101-42-6 (1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol 
• 84312-20-9 (1R,3R,4S)-8-phenylmenthyl glyoxylate 
• 129214-96-6 (-)-8-phenylneoisomenthyl glyoxylate 
• 100101-43-7 (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl glyoxylate 
• 80595-59-1 bromoacetic acid (-)-8-phenylmenthol ester 
• 129180-92-3 (-)-8-phenylneoisomenthyl bromoacetate 
• 129180-90-1 (+)-8-phenylisomenthyl bromoacetate 
• 104197-95-7 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate 
• 104197-95-7 Nitrooxy-acetic acid (1R,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 104197-95-7 Nitrooxy-acetic acid (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 71804-27-8 (1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate 
• 1433821-75-0 (-)-8-phenylisoneomenthyl glyoxylate oxime 

Relevant articles and documents

Diastereoselective photocycloaddition reactions of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furans governed by chiral auxiliaries and hydrogen bonding interactions

By using chiral auxiliaries and hydrogen bonding interactions, we have developed diastereoselective photocycloaddition of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furan derivatives. In photoreactions of (?)-menthyl 2-naphthalenecarboxylate with furan and 3-furanmethanol, respective maximum 48% and 40% diastereomeric excesses (d.e.) are observed. In photoreactions of di-8-phenyl-(?)-menthyl 2,3-naphthalenedicarboxylate with 3-furanmethanol, maximum 67% d.e. is obtained. Use of solvents of low polarity, low temperatures and low furan concentration leads to increased diastereoselectivities. Variable-temperature (VT) NMR and fluorescence quenching studies indicate that hydrogen bonding interactions between the carbonyl oxygen of naphthalenecarboxylic acid esters and the OH group in 3-furanmethanol take place in both the ground and excited states. The results of computational studies show that geometries of C2 symmetric naphthalenedicarboxylate reactants are important in governing the high diastereoselectivity in the photoreactions of 2,3-naphthalenedicarboxylates.

Synthesis and characterization of all stereoisomers of 8-phenylmenthol

New, improved and/or specific syntheses of the diastereoisomers of (-)-8-phenylmenthol are described. The configurations of these products, usable as chiral auxiliaries, were confirmed by X-ray diffractometry of their 3,5-dinitrobenzoates.

PREPARATION OF THREE DIASTEREOISOMERS OF 2-(1-METHYL-1-PHENYLETHYL)-5-METHYLCYCLOHEXAN-1-OL FROM (R)-(+)-PULEGONE

New isolation of (1R,2S,5R)-(-)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexan-1-ol ((-)-8-phenylmenthol, Ia), prepared from (R)-(+)-pulegone, is described.The method consists in the preparation of phenylcarbamate of Ia and its transesterification with ethanol.Further two diastereoisomers of (-)-8-phenylmenthol were isolated: the (1S,2R,5R)-isomer IIa and the (1R,2R,5R)-isomer IIIa.Compounds Ia, IIa and IIIa were converted into their respective glyoxylates Ic, IIc and IIIc.