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  Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. Marque Chem. Sci., 2021,12, 4154-4161
• 2. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
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• 4. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
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• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Prenol lipids Bicyclic monoterpenoids
• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Bicyclic monoterpenoids

(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol (CAS No. 51152-12-6): A Comprehensive Overview

(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol (CAS No. 51152-12-6) is a chiral compound with a unique bicyclic structure that has garnered significant attention in the fields of organic synthesis and medicinal chemistry. This compound is characterized by its 6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol core, which imparts specific stereochemical properties that make it a valuable intermediate in the synthesis of various biologically active molecules.

The (1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol structure is particularly noteworthy for its ability to serve as a chiral building block in the synthesis of natural products and pharmaceuticals. The chirality of this compound is crucial for its applications in asymmetric synthesis, where it can be used to introduce specific stereochemical configurations into target molecules. Recent studies have highlighted the importance of chiral intermediates in the development of enantiomerically pure drugs, which often exhibit superior pharmacological properties compared to their racemic counterparts.

In the context of organic synthesis, (1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol has been utilized in the synthesis of a variety of complex natural products and drug candidates. For example, a recent study published in the Journal of Organic Chemistry demonstrated the use of this compound as a key intermediate in the total synthesis of a potent anti-inflammatory agent. The researchers utilized a sequence of reactions involving (1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol to construct the target molecule with high stereoselectivity and yield.

The stereochemical properties of (1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol also make it an attractive candidate for use in medicinal chemistry applications. In particular, the compound's ability to influence the conformational behavior of larger molecules can be leveraged to optimize the binding affinity and selectivity of drug candidates. A study published in Medicinal Chemistry Research explored the use of (1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol as a scaffold for designing novel inhibitors of protein-protein interactions (PPIs). The researchers found that derivatives of this compound exhibited enhanced binding affinity and selectivity compared to existing inhibitors.

Furthermore, (1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol has been investigated for its potential applications in drug delivery systems. The unique bicyclic structure and chirality of this compound can be exploited to create prodrugs that are more stable and have improved pharmacokinetic properties compared to their parent drugs. A recent review article in Current Drug Delivery discussed several examples where (1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol was used as a prodrug moiety to enhance the oral bioavailability and reduce the toxicity of therapeutic agents.

The synthetic accessibility of (1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol has also been a subject of extensive research. Several efficient synthetic routes have been developed to produce this compound on both laboratory and industrial scales. One notable method involves a catalytic asymmetric hydrogenation reaction followed by selective functionalization steps to achieve high enantiomeric purity and yield. These advancements in synthetic methodology have made (1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol more readily available for use in various chemical and pharmaceutical applications.

In addition to its role as an intermediate and scaffold in chemical synthesis and drug development, (1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol has also been studied for its potential biological activities. Preliminary studies have shown that certain derivatives of this compound exhibit anti-inflammatory and anti-cancer properties in vitro and in animal models. For instance, a study published in Cancer Letters reported that a derivative of (1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol inhibited the growth of human cancer cells by inducing apoptosis and disrupting cell cycle progression.

The future prospects for (1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-ylmethanol are promising across multiple areas of research and development. Ongoing studies are focused on optimizing its synthetic routes to improve efficiency and scalability while exploring new applications in drug discovery and delivery systems. As our understanding of chiral chemistry continues to advance, it is likely that this compound will play an increasingly important role in shaping the landscape of modern medicinal chemistry.

• 61314-58-7(Bicyclo[3.1.1]heptane-2-methanol, 3,6,6-trimethyl-)
• 15358-92-6(Bicyclo[3.1.1]heptane-2-methanol,6,6-dimethyl-, (1R,2S,5R)-rel-)
• 514-99-8(Bicyclo[3.1.1]heptane-2-methanol,6,6-dimethyl-)
• 56587-70-3(Bicyclo[3.1.1]heptane-3-methanol, 2,6,6-trimethyl-)
• 919482-25-0(Spiro[3.5]nonane-5-methanol)
• 132203-71-5(( )-TRANS-MYRTANOL)
• 15358-91-5(Bicyclo[3.1.1]heptane-2-methanol,6,6-dimethyl-, (1R,2R,5R)-rel-)
• 53369-17-8((-)-trans-Myrtanol)
• 473-01-8(Bicyclo[3.1.1]heptane-2-methanol,6,6-dimethyl-, (1R,2S,5R)-)
• 1082373-80-5(7-Hydroxymethyl-spiro3.5nonane)