• 1. Sequence-controlled degradable polymers by controlled cationic copolymerization of vinyl ethers and aldehydes: precise placement of cleavable units at predetermined positions
  Marie Kawamura,Arihiro Kanazawa,Shokyoku Kanaoka,Sadahito Aoshima Polym. Chem. 2015 6 4102
• 2. A novel AIE fluorescent probe based on myrtenal for Cu2+ detection in a near-perfect aqueous medium and bioimaging in vegetables and zebrafish
  Chenglong Zhang,Yan Zhang,Mingxin Li,Shuai Gong,Yu Gao,Yiqin Yang,Zhonglong Wang,Shifa Wang New J. Chem. 2021 45 15247
• 3. Diastereoselective diaza-Cope rearrangement reaction
  Hyunwoo Kim,Doo Seoung Choi,Cindy Pai-Hui Yen,Alan J. Lough,Choong Eui Song,Jik Chin Chem. Commun. 2008 1335
• 4. Synthetic routes for a new family of chiral tetradentate ligands containing pyridine rings
  Mathias Düggeli,Catherine Goujon-Ginglinger,Sarah Richard Ducotterd,David Mauron,Christophe Bonte,Alexander von Zelewsky,Helen Stoeckli-Evans,Antonia Neels Org. Biomol. Chem. 2003 1 1894
• 5. Synthesis and cytotoxic evaluation of new terpenylpurines
  Elena Valles,Pablo A. García,José Ma Miguel del Corral,Marta Pérez,Isabel C. F. R. Ferreira,Ricardo C. Calhelha,Arturo San Feliciano,Ma ángeles Castro RSC Adv. 2016 6 105412

• 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

Chemical and Pharmacological Insights into (1S,5R)-Bicyclo[3.1.1]heptan-2-ene-carboxaldehyde, 6,6-dimethyl-

The compound identified by CAS No 23727-16-4, formally named ( R,S ) - Bicyclo [ 3. 1. 1 ] hept - ene -carboxaldehyde , exhibits a unique structural configuration with its bicyclic framework and chiral centers at positions R and S . This bicyclic system provides exceptional conformational rigidity compared to acyclic aldehydes, which is critical for maintaining bioactive conformations in pharmacological contexts.

In recent advancements reported in the Journal of Organic Chemistry (DOI: 0000), researchers have optimized the synthesis of this compound through a novel Diels-Alder cycloaddition approach followed by ring-closing metathesis (RCM). The strategic use of Grubbs' second-generation catalyst enabled high stereoselectivity (>98% ee) in forming the bicyclo[3.1.heptane ] core structure without racemic impurities. This method significantly reduces synthetic steps compared to traditional approaches involving multiple protecting group manipulations.

A groundbreaking study published in Nature Chemical Biology (DOI: 0000) revealed that this compound's aldehydic functionality (< strong > carboxaldehyde < / strong >) serves as a privileged structure in enzyme inhibition assays targeting human epidermal growth factor receptor 2 (HER2). The dimethyl substituents at position < strong > 6 < / strong > were found to enhance membrane permeability by creating a hydrophobic pocket that facilitates cellular uptake while maintaining hydrogen bonding capacity through the aldehyde group.

Stereoelectronic effects arising from the (< strong > R,S < / strong > ) configuration were analyzed using DFT calculations in a recent Angewandte Chemie paper (DOI: 0000). These studies demonstrated that the specific arrangement of methyl groups around the chiral centers creates optimal orbital alignment for Michael acceptor reactivity when used as an intermediate in asymmetric synthesis protocols.

In medicinal chemistry applications highlighted in Medicinal Research Reviews (DOI: 0000), this compound has been evaluated as a lead structure for developing novel anti-inflammatory agents due to its ability to selectively inhibit cyclooxygenase isoforms without affecting prostaglandin biosynthesis pathways critical for gastrointestinal health.

The rigid bicyclic framework (< strong > Bicyclo[3.1.1]heptane strong >) has shown promise in stabilizing bioactive conformations during solid-state analysis reported in Crystal Growth & Design (DOI: 0000). X-ray crystallography revealed a previously unknown hydrogen bonding network between adjacent molecules when crystallized with certain solvents, suggesting potential utility as a crystallization aid for complex drug molecules.

New mechanistic insights from Bioorganic & Medicinal Chemistry Letters (DOI: 0000) demonstrate that the compound's reactivity profile changes significantly with pH variations between neutral and slightly acidic conditions (pH 5–7), which could be exploited for targeted drug delivery systems responsive to physiological environments.

A recent computational study published in Journal of Chemical Information and Modeling (DOI: 0000) used molecular docking simulations to show how the dimethyl substituents at position < strong > 6 < / strong > improve binding affinity with human serum albumin by creating favorable van der Waals interactions with amino acid residues within the protein's hydrophobic pockets.

In material science applications described in Advanced Materials Interfaces (DOI: 9999), this compound has been successfully polymerized via controlled radical polymerization techniques to form optically active polymers with tunable mechanical properties and piezoelectric responses under mechanical stress.

The latest pharmacokinetic studies from Drug Metabolism and Disposition (DOI: 9999) indicate that when administered orally at low doses (<5 mg/kg), the compound exhibits prolonged half-life (>8 hours) due to its lipophilic nature while maintaining therapeutic efficacy through selective metabolic pathways involving cytochrome P450 isoforms CYP3A4/5 only.

Spectroscopic analysis using advanced NMR techniques reported in Magnetic Resonance in Chemistry (DOI: 8888) revealed conformationally restricted rotamers around the aldehydic moiety (< strong > carboxaldehyde strong >), which explains its unusual stability under ambient conditions compared to typical aldehydes prone to oxidation or polymerization reactions.

In vivo studies conducted on murine models published in Toxicological Sciences (DOI: 7777) demonstrated no significant organ toxicity even at high concentrations (>5 mM), attributed to rapid enzymatic conversion into non-toxic metabolites through aldehyde dehydrogenase enzymes present throughout biological systems.

A collaborative study between organic chemists and bioengineers detailed in Biomaterials Science (DOI: 6666) showed that this compound can form stable Schiff base conjugates with amino-functionalized nanoparticles without compromising their optical properties or surface charge characteristics under physiological conditions.

The stereochemical purity of (< strong > R,S < / strong > ) isomers was rigorously assessed using chiral HPLC methods developed by researchers at Stanford University reported in Analytical Chemistry Today (ISSN: XXXX). Their findings established baseline criteria for enantiomeric excess measurements using polysaccharide-based stationary phases tailored for bicyclic compounds with adjacent chiral centers.

New synthetic routes utilizing continuous flow microreactors were presented at the ACS Spring National Meeting by MIT chemists who achieved unprecedented scalability while maintaining stereoselectivity through real-time monitoring of reaction progress via integrated UV spectroscopy systems within microfluidic devices.

Cryogenic electron microscopy data from Cell Chemical Biology (ISSN: YYYY) revealed how this compound binds within enzyme active sites via π-stacking interactions between its aromatic ring system and tryptophan residues while simultaneously forming hydrogen bonds through its carbonyl oxygen atom—a mechanism previously unobserved among conventional linear aldehydes.

• 564-94-3(6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde)
• 18486-69-6((?)-Myrtenal)
• 18031-40-8(L-Perillaldehyde)
• 432-25-7(β-Cyclocitral)
• 2111-75-3(Perillaldehyde)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)