1,5-dimethyl Bicyclo[3.1.1]heptane-1,5-dicarboxylate

Dimethyl bicyclo[3.1.1]heptane-1,5-dicarboxylate is a white to off-white crystalline solid with a melting point between 182 and 186°C.It is recommended to store it at room temperature.The compound has low water solubility but is readily soluble in polar aprotic solvents such as tetrahydrofuran(THF),1,4-dioxane,and N,N-dimethylformamide(DMF).It shows moderate solubility in ethyl acetate and dichloromethane and is insoluble in non-polar solvents like n-hexane.It is chemically stable under dry conditions and inert atmospheres.The ester groups are susceptible to hydrolysis under strongly acidic or basic aqueous conditions at elevated temperatures.

Dimethyl bicyclo[3.1.1]heptane-1,5-dicarboxylate(CAS No.75328-54-0)is a diester derivative of noradamantane(bicyclo[3.1.1]heptane),a rigid,aliphatic,cage-like hydrocarbon.This compound serves as a valuable,conformationally constrained building block for introducing three-dimensional character into organic molecules,a desirable property in modern medicinal chemistry.

1.Building Block for Protease Inhibitors
The noradamantane core provides exceptional rigidity and defined vectors for substituents.It is incorporated into the backbone of designed peptides to create potent and selective inhibitors of serine proteases like kallikrein-related peptidases(KLKs),targets for treating inflammatory diseases and cancer.

2.Monomer for High-Tg Engineering Plastics
Hydrolyzed to the corresponding diacid and polymerized with various diamines to yield polyamides(nylons)with exceptionally high glass transition temperatures(Tg>250°C)and optical clarity,suitable for demanding automotive and aerospace components.

3.Template for Spirocyclic Ligand Synthesis
The two ester groups are strategically reduced to hydroxymethyl groups and further elaborated to create chelating bis-phosphine or bis-N-heterocyclic carbene(NHC)ligands.The rigid scaffold enforces precise metal coordination geometry,enhancing selectivity in asymmetric hydrogenation catalysts.

4.Molecular Scaffold in Crystal Engineering
Used as a ditopic hydrogen-bond acceptor(via ester carbonyls)in the design of co-crystals with complementary hydrogen-bond donors.This aids in the systematic study of packing motifs and the development of pharmaceutical co-crystals to improve drug solubility.