100101-42-6

Basic information

• Product Name: (1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol
• Synonyms: (1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol
• CAS NO: 100101-42-6
• Molecular Weight: 232.366
• Mol File: 100101-42-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol(100101-42-6)
• EPA Substance Registry System: (1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol(100101-42-6)

Safety Data

• Hazardous Substances Data: 100101-42-6(Hazardous Substances Data)

Usage

General Description

The chemical compound (1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol, also known as pseudoephedrine, is a decongestant used to relieve nasal congestion caused by allergies, colds, or other respiratory conditions. It works by narrowing the blood vessels in the nasal passages, reducing swelling and congestion. Pseudoephedrine is a stereoisomer of ephedrine and has similar stimulant and decongestant properties. It is commonly found in over-the-counter cold and allergy medications and has a potential for misuse and abuse due to its stimulant effects. Pseudoephedrine is regulated in many countries and is often subject to restrictions on purchase and distribution due to its potential for use in the illicit production of methamphetamine.

Upstream product

• 104870-80-6 (1R,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol 
• 5949-05-3 (S)-Citronellal 
• 98-09-9 benzenesulfonyl chloride 
• 363583-56-6 (1R,2R,5R)-S-methyl-O-[5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl]dithiocarbonate 
• 363583-57-7 (3R,6S)-3-methyl-6-(1-methyl-1-phenylethyl)-1-cyclohexene 
• 363583-58-8 (1R,2S,3R,6R)-1,2-epoxy-3-methyl-6-(1-methyl-1-phenylethyl)cyclohexane 
• 104870-79-3 (2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanone 
• 129180-87-6 Phenyl-carbamic acid (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 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 
• 89-82-7 pulegone 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 127215-54-7 (E)-2-Methyl-3-[5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxy]-propenal 
• 127215-54-7 (E)-2-Methyl-3-[5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxy]-propenal 
• 129180-91-2 1-(1-methyl-1-phenylethyl)-4-methylcyclohexene 
• 129180-90-1 (+)-8-phenylisomenthyl bromoacetate 
• 100101-44-8 (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl pyruvate 
• 65253-04-5 (-)-8-phenylmenthol 
• 104870-80-6 (1R,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 
• 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 

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.

Enantioselective synthesis of [(1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept- 5-en-3-yl]methanol via Aza-Diels-Alder reaction

The asymmetric aza-Diels-Alder reaction of the 8-phenylneomenthyl (or 8-phenylisomenthyl) glyoxylate-derived N-benzylimine with cyclopentadiene resulted in the enantioselective synthesis of the corresponding [(1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-

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.