104870-75-9

Basic information

• Product Name: (1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanol
• CAS NO: 104870-75-9
• Molecular Formula: C₁₆H₂₄O
• Molecular Weight: 232.3612
• Mol File: 104870-75-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 333.098°C at 760 mmHg
• Flash Point: 138.155°C
• Density: 0.986g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: (1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanol(104870-75-9)
• EPA Substance Registry System: (1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanol(104870-75-9)

Safety Data

• Hazardous Substances Data: 104870-75-9(Hazardous Substances Data)

Upstream product

• 205057-17-6 (5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanone 
• 100-58-3 phenylmagnesium bromide 
• 89-82-7 pulegone 
• 97371-54-5 (-)-(2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanon 
• 5949-05-3 (S)-Citronellal 
• 98-09-9 benzenesulfonyl chloride 
• 104870-79-3 (2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanone 
• 104870-80-6 (1R,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol 
• 65253-04-5 (-)-8-phenylmenthol 
• 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 
• 1427281-84-2 (+)-(1S,2S,5R)-8-phenylneomenthyl (2R)-4-oxo-1-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate 

Downstream Products

• 129180-87-6 (-)-8-phenylmenthol phenylcarbamate 
• 129180-87-6 Phenyl-carbamic acid (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 129180-87-6 Phenyl-carbamic acid (1R,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 75863-05-7 Malonic acid bis-[(2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester 
• 97371-54-5 (-)-(2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanon 
• 849113-76-4 (+)-(1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl acrylate 
• 322640-03-9 (1S,2S,5R)-5-methyl-2-[1-methyl-(1-phenyl)ethyl]cyclohexyl acetate 
• 322640-04-0 (1S,2S,5R)-5-methyl-2-[1-methyl-(4-nitrophenyl)ethyl]cyclohexyl acetate 
• 322640-41-5 (1S,2S,5R)-5-methyl-2-[1-methyl-(4-nitrophenyl)ethyl]cyclohexanol 
• 322640-70-0 (1S,4aS,10aS)-7-Isopropyl-8-methoxy-4a-methyl-2-oxo-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid (1S,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 322640-53-9 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1S,2S,5R)-5-methyl-2-[1-methyl-1-(4-nitro-phenyl)-ethyl]-cyclohexyl ester 
• 1427281-86-4 (+)-(1S,2S,5R)-8-phenylneomenthyl (2R)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate 
• 1427281-84-2 (+)-(1S,2S,5R)-8-phenylneomenthyl (2R)-4-oxo-1-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate 
• 1427281-90-0 (+)-(1S,2S,5R)-8-phenylneomenthyl (2R)-4-oxo-1-[(1S)-1-phenylethyl]piperidine-2-carboxylate 

Relevant articles and documents

A short, efficient synthesis of the chiral auxiliary (+)-8- phenylneomenthol

(+)-8-Phenylneomenthol 2, the structure of which was confirmed by X-ray analysis of its 3,5-dinitrobenzoate, was efficiently prepared from commercially available (-)-8-phenylmenthol 3 by oxidation with the Sarett reagent, followed by L-Selectride reduction of the (+)-8-phenylmenthone 6 thus formed. (C) 2000 Elsevier Science Ltd.

Synthesis of the Privileged 8-Arylmenthol Class by Radical Arylation of Isopulegol

Hydrogen atom transfer (HAT) circumvents a disfavored Friedel-Crafts reaction in the derivatization of the inexpensive monoterpene isopulegol. A variety of readily prepared aryl and heteroaryl sulfonates undergo a formal hydroarylation to form 8-arylmenthols, privileged scaffolds for asymmetric synthesis, as typified by 8-phenylmenthol. High stereoselectivity is observed in related systems. This use of HAT significantly extends the chiral pool from the inexpensive monoterpene isopulegol.

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.