105970-13-6

Basic information

• Product Name: (1R,2S,5R)-8-(β-naphthyl)menthol
• Synonyms: (1R,2S,5R)-8-(β-naphthyl)menthol
• CAS NO: 105970-13-6
• Molecular Weight: 282.426
• Mol File: 105970-13-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (1R,2S,5R)-8-(β-naphthyl)menthol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,5R)-8-(β-naphthyl)menthol(105970-13-6)
• EPA Substance Registry System: (1R,2S,5R)-8-(β-naphthyl)menthol(105970-13-6)

Safety Data

• Hazardous Substances Data: 105970-13-6(Hazardous Substances Data)

Upstream product

• 105970-10-3 8-β-naphthylmenthone 
• 128797-14-8 (4aS,8aR)-4-Oxo-decahydro-naphthalene-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 
• 126328-89-0 tert-butyl(3-(iodomethyl)phenoxy)dimethylsilane 
• 278595-59-8 (1'R,2'S,5'R)-8'-(β-naphthyl)menthyl N-benzoyl-(Z)-dehydrobutyrinate 
• 100-39-0 benzyl bromide 
• 69730-71-8 1-iodo-3-benzaldiminopropane 
• 107-08-4 1-iodo-propane 
• 144541-38-8 <1R-(1α,2α,5α)>-5-Methyl-2-(1-methylethenyl)cyclohexanol 
• 93-11-8 2-Naphthalenesulfonyl chloride 
• 21473-01-8 2-naphthalenylmagnesium bromide 
• 89-82-7 pulegone 
• 105970-10-3 (2S,5R)-5-Methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexanone 
• 278595-44-1 α-(1'R,2'S,5'R)-8-(β-naphthyl)menthyl β-ethyl N-benzoyl-L-α-vinylaspartate 
• 278595-39-4 (1'R,2'S,5'R)-8'-(β-naphthyl)menthyl N-benzoyl-L-α-vinylleucinate 

Downstream Products

• 152481-93-1 (1R,2S,5R)-(+)-2-(1-methyl-1-β-naphthylethyl)-5-methylcyclohexyl dichloroacetate 
• 160946-53-2 4,4-Dimethoxy-3-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 
• 278595-59-8 (1'R,2'S,5'R)-8'-(β-naphthyl)menthyl N-benzoyl-(Z)-dehydrobutyrinate 
• 322640-52-8 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 
• 668452-70-8 (-)-(1R,2S,5R)-5-methyl-2-[1-methyl-1-(2-naphthyl)ethyl]cyclohexyl cyclohexen-3-one-1-carboxylate 
• 259733-46-5 (1R,2S,5R)-2-[1-methyl-(2-naphthyl)ethyl]-5-methylcyclohexyl (E)-3-methyl-2-tridecen-7-ynoate 
• 732302-17-9 2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-(β-naphthyl)menthol ester 
• 186045-34-1 4-Oxo-piperidine-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 
• 211503-79-6 ({(1R,2S,5R)-5-methyl-2-[1-methyl-1-(2-naphthyl)ethyl]cyclohexyl}oxy)carbonylhydroxylamine 

Relevant articles and documents

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.

Engineering Acyclic Stereocontrol in the Alkylation of Vinylglycine-Derived Dianions: Asymmetric Synthesis of Higher α-Vinyl Amino Acids

A generalizable synthesis of higher L-α-vinyl amino acids is presented. The strategy pursued here involves the introduction of the amino acid side chain via the alkylation of a chiral, vinylglycine-derived dianionic dienolate, bearing the (-)-8-(β-naphthyl)menthyl (d'Angelo) auxiliary. A model is presented that postulates a favored "exo-entended" conformation for this dienolate, leading to Cα-alkylation at the si face. The model invokes internal amidate chelation to control ester enolate geometry and soft-soft interactions between the polarizable β-naphthyl ring of the auxiliary and the extended π-system of the dienolate to shield the re face. Heats of formation for four conformers of this dianion were calculated for their semiempirical optimized geometries (PM3). The results support the notion that in these vinylglycine-derived dianionic dienolates, "exo" conformations are considerable lower in energy than their "endo" counterparts, with the "exo-entended" conformation being most favorable. In fact, the d'Angelo auxiliary gives a greater degree of acyclic stereocontrol in this system when compared with the (-)-8-phenylmenthyl (Corey) and trans-2-(β-naphthyl)-cyclohexyl auxiliaries, using isobutyl iodide and benzyl bromide as model electrophiles. These dianions are generated from the corresponding dehydrobutyrine esters via sequential deprotonation with LDA and n-BuLi (2 equiv). When alkylations are carried out at -78°C in THF-HMPA, they proceed in 65-81% yields, with both regiocontrol (deconjugative α-alkylation is preferred over γ-alkylation) and a great degree of acyclic stereocontrol [91:9 to ≥98:2 diastereomeric ratios (10 examples)]. The auxiliary may be recovered in high yield (generally 90%) using a modification of Gassman's "anhydrous hydroxide" conditions, in which considerably higher temperatures are employed. Among the side chains introduced directly are those of butyrine, leucine, ornithine, phenylalanine, aspartate, valine, and norvaline. The lysine side chain is elaborated via a 4-step sequence from the alkylation product obtained with 1-chloro-4-iodobutane as electrophile. Importantly, to our knowledge, this work represents the first asymmetric synthesis of L-α-vinyl analogues of m-tyrosine, ornithine, and lysine, known time-dependent inhibitors for amino acid decarboxylases.

Improved Asymmetric Synthesis of 8-Arylmenthols

A two-step synthesis of a set of arylmenthones 3 from R(+)-pulegone 2 via their silylenoethers 4 is proposed leading in high yields to 8-arylmenthols 1.