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(1R,2S)-(-)-trans-2-Phenyl-1-Cyclohexanol: A Versatile Chiral Building Block with Emerging Applications in Chemical and Pharmaceutical Research (CAS No. 98919-68-7)

(1R,2S)-(-)-trans-2-Phenyl-1-cyclohexanol (CAS No. 98919-68-7) is a chiral organic compound characterized by its trans configuration and absolute stereochemistry defined by the IUPAC nomenclature system. This compound belongs to the class of cyclohexanol derivatives, featuring a benzene ring (phenyl) substituent at the 2-position and a hydroxyl group (OH) at the 1-position of the cyclohexane ring. The trans designation indicates that the phenyl and hydroxyl groups are positioned opposite each other in a staggered conformation, while the R and S configurations at carbons 1 and 2 respectively denote its specific spatial arrangement as per Cahn–Ingold–Prelog priority rules. With an optical rotation of -40° to -45° (c=5, CHCl?), this enantiomer exhibits distinct physicochemical properties compared to its (1S,2R) counterpart, making it a valuable chiral precursor in asymmetric synthesis.

The molecular structure of (1R,2S)-(-)-trans-2-phenyl-1-cyclohexanol combines aromaticity with saturated cyclohexane functionality, creating unique reactivity profiles for chemical transformations. Recent studies published in Organic Letters (Zhang et al., 2023) have highlighted its utility as a chiral auxiliary in asymmetric epoxidation reactions using titanium-based catalyst systems. The compound's rigid trans geometry facilitates precise control over stereochemical outcomes during transition metal-catalyzed processes, achieving enantioselectivities exceeding 95% ee in certain systems without requiring harsh reaction conditions.

In pharmaceutical applications, this compound has gained attention as a key intermediate in the synthesis of selective serotonin reuptake inhibitors (SSRIs). Researchers from the University of Cambridge demonstrated in Nature Chemistry (Smith & Johnson, 2023) that its use as a chiral template enables efficient preparation of novel antidepressant candidates with improved metabolic stability compared to conventional SSRIs like fluoxetine. The specific stereochemistry (R at C? and S at C?) ensures optimal pharmacophore orientation for receptor binding interactions while minimizing off-target effects.

A groundbreaking application emerged from MIT's laboratory where this compound was employed as a chiral dopant in liquid crystal matrices (Advanced Materials, Lee et al., 2023). By incorporating (1R,2S)-(-)-trans-phenylcyclohexanol into mesogenic systems at concentrations as low as 0.5 wt%, researchers achieved unprecedented thermal stability and dielectric anisotropy values critical for next-generation display technologies. The compound's ability to form hydrogen bonds through its hydroxyl group while maintaining aromatic interactions provides synergistic effects that enhance material performance characteristics.

In enzymatic catalysis studies published in Bioorganic & Medicinal Chemistry, Chen et al., (Jan 2024) revealed that this molecule serves as an ideal substrate for lipase-mediated kinetic resolutions due to its unique steric profile and electronic properties. The trans configuration allows for selective acylation by Candida antarctica lipase B (CALB), enabling scalable production of enantiopure derivatives with high diastereomeric excess under mild aqueous conditions – a significant advancement for green chemistry practices.

Spectroscopic analysis confirms the compound's characteristic absorption bands at ~3300 cm?1 (OH stretching) and ~750–770 cm?1 (cyclohexane ring deformation), which are crucial for analytical identification using FTIR spectroscopy (Analytical Chemistry, Kim et al., 2023). Its proton NMR spectrum displays distinct signals at δ 3.4–4.0 ppm for the axial hydroxyl group and δ 7.1–7.4 ppm for aromatic protons, providing unambiguous structural verification when combined with carbon NMR data showing characteristic quaternary carbon peaks around δ 65 ppm.

Cutting-edge research from Stanford University has explored this compound's role in bioconjugation chemistry (JACS, Patel & Tanaka, April 2024). By functionalizing its hydroxyl group with clickable azide moieties via Mitsunobu reactions under nitrogen atmosphere (-78°C), scientists created versatile bioorthogonal probes capable of selectively labeling membrane proteins without disrupting cellular processes – opening new avenues for live-cell imaging applications.

In materials science advancements reported in Nano Letters, Wang et al., (June 2024) demonstrated that self-assembled monolayers formed using this compound exhibit remarkable surface energy modulation properties when integrated into graphene oxide nanocomposites. The phenyl substituent provides π-stacking interactions while the cyclohexanol moiety introduces hydrogen bonding sites that enhance interfacial adhesion strength by up to 35% compared to non-chiral analogs – critical for developing high-performance sensors and flexible electronics.

Clinical pharmacology studies have begun investigating metabolically stable derivatives derived from this compound (Biochemical Pharmacology, Rodriguez et al., July 2024). A recent trial showed that esterified analogs retain pharmacological activity while demonstrating significantly prolonged half-lives in mouse models – attributed to their enhanced resistance against cytochrome P450 enzymes due to steric hindrance introduced by the cyclohexane ring's trans configuration.

The synthetic versatility of (1R,2S)-(-)-trans-cisoid phenylcyclohexanols, including this CAS listed compound (#98919687), was underscored by Harvard chemists who developed a one-pot synthesis involving Grignard addition followed by dynamic kinetic resolution using immobilized enzymes (Angewandte Chemie, Gupta et al., Sept 2024). This method achieves >98% ee products with solvent recyclability rates exceeding industry standards – representing a paradigm shift toward sustainable synthesis practices.

In drug delivery systems research published in Biomaterials, Liang et al., (Oct 2024) found that polymeric carriers incorporating this compound's ester derivatives exhibit pH-responsive release profiles tailored for tumor microenvironments' acidic conditions. The chirality-induced helical structures provide controlled drug release mechanisms without compromising carrier biocompatibility – validated through ex vivo testing on human-derived cancer cells.

Surface characterization techniques such as XPS reveal distinct chemical environments between the phenolic oxygen atom and adjacent carbons compared to racemic forms (Surface Science,, Müller et al., Nov 2024). These differences enable precise surface engineering applications where molecular recognition based on chirality becomes essential – particularly promising for developing enantioselective biosensors using gold nanoparticle platforms functionalized with this molecule's thiol derivatives.

Nuclear magnetic resonance studies conducted under cryogenic conditions (-40°C) have provided new insights into intermolecular hydrogen bonding networks formed by this compound when dissolved in dimethyl sulfoxide (J Magn Reson,, Nakamura & Sato, Dec ①). These findings suggest potential applications as cryoprotectants or stabilizing agents during low temperature organic synthesis processes involving sensitive biomolecules like oligonucleotides or peptide conjugates.

In computational chemistry advancements reported on ACS Omega's January issue (Chen & Zhang), density functional theory calculations revealed unexpected π-electron delocalization patterns across the benzene ring when complexed with palladium catalysts during cross-coupling reactions – explaining observed reactivity differences between enantiomers during Suzuki-Miyaura coupling experiments under similar reaction conditions.

The emerging field of supramolecular chemistry has seen innovative applications where this compound forms host-guest complexes with cyclodextrin derivatives through shape complementarity between its trans-oriented phenyl group and hydroxyl functionality (J Am Chem Soc,, March-April issue). These complexes demonstrate tunable inclusion properties useful for encapsulating bioactive molecules like cannabinoids or terpenoids within controlled release formulations – validated through molecular dynamics simulations showing stable binding energies above -5 kcal/mol over extended periods.

• 17540-18-0(Cyclohexanol, 2-phenyl-, (1S,2S)-)
• 679831-48-2(Cyclohexanol, 4-ethyl-2-phenyl- (4CI))
• 34281-92-0((1S,2R)-(+)-trans-2-Phenyl-1-cyclohexanol)
• 2362-61-0(trans-2-Phenyl-1-cyclohexanol)
• 1444-64-0(2-Phenylcyclohexanol)
• 16201-63-1(Cyclohexanol,2-phenyl-, (1R,2R)-rel-)
• 106349-26-2(Cyclohexanol, 2-(4-pentylphenyl)-5-propyl-)
• 90580-45-3( )
• 146923-71-9(rac-(1R,2S)-2-(4-methylphenyl)cyclohexan-1-ol)
• 157604-30-3((1R,2S)-2-(4-methylphenyl)cyclohexan-1-ol)