240117-99-1

Basic information

• Product Name: (1R,2R,4S)-2-(2-METHOXY-PHENYL)-1,3,3-TRIMETHYL-BICYCLO[2.2.1]HEPTAN-2-OL
• Synonyms: (1R,2R,4S)-2-(2-METHOXY-PHENYL)-1,3,3-TRIMETHYL-BICYCLO[2.2.1]HEPTAN-2-OL
• CAS NO: 240117-99-1
• Molecular Formula: C17H24O2
• Molecular Weight: 260.37126
• Mol File: 240117-99-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,2R,4S)-2-(2-METHOXY-PHENYL)-1,3,3-TRIMETHYL-BICYCLO[2.2.1]HEPTAN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,4S)-2-(2-METHOXY-PHENYL)-1,3,3-TRIMETHYL-BICYCLO[2.2.1]HEPTAN-2-OL(240117-99-1)
• EPA Substance Registry System: (1R,2R,4S)-2-(2-METHOXY-PHENYL)-1,3,3-TRIMETHYL-BICYCLO[2.2.1]HEPTAN-2-OL(240117-99-1)

Safety Data

• Hazardous Substances Data: 240117-99-1(Hazardous Substances Data)

Upstream product

• 578-57-4 2-bromoanisole 
• 4695-62-9 fenchone 
• 100-66-3 methoxybenzene 
• 7787-20-4 (1R)-fenchone 
• 31600-86-9 2-methoxyphenyllithium 

Relevant articles and documents

Enantiopure Methyl- A nd Phenyllithium: Mixed (Carb-)Anionic Anisyl Fencholate-Aggregates

Methyl- A nd phenyllithium aggregates with enantiopure anisyl fencholate units form after reaction of organolithium reagent with (+)-anisyl fenchol in hydrocarbon and some ethereal solvents. These carbanionic aggregates are characterized by X-ray crystal analyses and exhibit both 3:1 stoichiometry and distorted cubic Li4O3C1 cores, in which three lithium ions coordinate the carbanion (i.e., methylide or phenylide). These three lithium ions define a Lewis acidic surface (Li3), binding the carbanion and expanding with the steric demand of the carbanion (i.e., from Me: 2.62 ?2, over n-Bu: 2.65 ?2 (previous work) to Ph: 2.79 ?2). Methylation and phenylation reactions of various prochiral aldehydes employing these methyllithium and phenyllithium aggregates yield alcohols with up to 44% ee. To rationalize the formation of the mixed (carb-)anionic aggregates, aggregate formation energies, describing co-condensations of RLi (R = Me, Ph, n-Bu) and lithium fencholates, are computed for the 3:1 and 2:2 stoichiometries. These computed aggregate formation energies point to preferences for 3:1 over 2:2 aggregates, as it is also apparent from experimental aggregate formations, confirmed by X-ray crystal analyses. In close analogy to the X-ray crystal structures, the computed Li3 surfaces increase with increasing steric demand of the carbanions. The chiral, mixed (carb-)anionic RLi-fencholate aggregates hence adapt to different carbanion sized and arise not only with small (Me) or primary carbanions (n-Bu) but even with the larger secondary phenyl anion.

Rationalization of Enantioselectivities in Dialkylzinc Additions to Benzaldehyde Catalyzed by Fenchone Derivatives

Three (-)-fenchyl alcohol derivatives, {(1R,2R,4S)-exo-(2-Ar)-1,3,3-trimethylbicyclo[2.2.1] heptan-2-ol, Ar = o-anisyl (2), 2-N-methylimidazolyl (3), 2-N,N-dimethylbenzylamine (4)} were synthesized, characterized by X-ray analyses, and employed as precata

Tandem Wagner-Meerwein rearrangement-carbocation trapping in the formation of chiral heterocyclic ring systems

Ortho lithiated protected anilines and phenols undergo exclusive addition to fenchone from the exo face. The corresponding adducts, under acidic conditions undergo cationic rearrangement followed by internal trapping of the new cation with amino, hydroxyl or methoxyl substituents to give enantiomerically pure chiral heterocyclic ring systems. The nature of the rearrangement is dependent on the donor group and ifs ability to stabilise a positive charge. With an amino donor group a product due to Wagner-Meerwein rearrangement is formed while with a methoxy donor group Nametkin rearrangement is the preferred pathway.