Methyl 5-(hydroxymethyl)bicyclo[3.1.1]heptane-1-carboxylate

Methyl 5-(hydroxymethyl)bicyclo[3.1.1]heptane-1-carboxylate is a white to off-white crystalline solid at room temperature with a melting point between 156 and 160°C.Its predicted boiling point is 254.2±13.0°C,and the estimated density is 1.220±0.06 g/cm³.The predicted pKa is 15.24±0.10.It is stable for storage at room temperature under dry conditions.This compound shows limited water solubility but is highly soluble in polar aprotic solvents such as tetrahydrofuran(THF),dimethylformamide(DMF),and dimethyl sulfoxide(DMSO).It is also soluble in methanol and ethanol,shows moderate solubility in dichloromethane and ethyl acetate,and is insoluble in non-polar solvents like n-hexane and petroleum ether.The molecule contains both an ester and a primary alcohol,making it sensitive to strong acids,bases,and oxidizing agents.The primary alcohol can oxidize over time if exposed to air.

Methyl 5-(hydroxymethyl)bicyclo[3.1.1]heptane-1-carboxylate(CAS No.2091771-31-0)is a noradamantane(bicyclo[3.1.1]heptane)derivative functionalized with a methyl ester at the 1-position and a hydroxymethyl group at the 5-position.This structure provides a rigid,three-dimensional aliphatic scaffold with two orthogonal reactive handles(ester and alcohol),making it a valuable chiral building block for fragment-based drug discovery and materials science.

1.Chiral Auxiliary for Asymmetric Synthesis
The rigid noradamantane core serves as a backbone for developing novel chiral oxazolidinone auxiliaries.The hydroxymethyl group is converted to a carbamate,creating a Evans-type auxiliary that provides exceptional diastereoselectivity in aldol and alkylation reactions for synthesizing enantiopureα-amino acids andβ-hydroxy carbonyl compounds.

2.Monomer for High-Performance Polyesters
Co-polymerized with aliphatic or aromatic diacids via enzymatic polymerization using Candida antarctica lipase B.The resulting polyesters,incorporating the bulky noradamantane unit,exhibit high thermal stability(Tg>120°C),transparency,and low birefringence,making them suitable for optical lens resins and advanced packaging films.

3.Template for Metal-Organic Cage Construction
The two functional groups are used to install pyridine or carboxylate ligands.These functionalized cages self-assemble with metal ions(Pd²⁺,Pt²⁺)to form discrete,three-dimensional metallosupramolecular cages capable of selectively binding small gaseous molecules like CO₂or Xe for separation applications.

4.Building Block for Bioactive Conjugates
The alcohol is selectively phosphorylated to create prodrug motifs,while the ester is hydrolyzed to the acid for conjugation to peptides.This bifunctional capability is used to synthesize cell-penetrating peptide conjugates of antivirals,enhancing their delivery across the blood-brain barrier for treating neurotropic infections.