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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Dioxanes 1,4-dioxanes
• Solvents and Organic Chemicals Organic Compounds Heterocyclic Compounds

Chemical Profile and Applications of 3,6-Dioxabicyclo[3.1.0]hexane (CAS No: 285-69-8)

3,6-Dioxabicyclo[3.1.0]hexane, identified by its unique CAS number 285-69-8, is a bicyclic organic compound that has garnered significant attention in the fields of synthetic chemistry and biomedical research due to its structural versatility and functional reactivity. The compound's core framework consists of a six-membered ring system with two oxygen atoms positioned at the 3 and 6 carbon atoms, forming a strained yet stable heterocyclic structure known as a dioxabicyclic ring system (DIOXABICYCLOHEXANE). This molecular architecture enables it to serve as a valuable intermediate in the synthesis of complex molecules such as alkaloids, heterocyclic drugs, and functional polymers.

The structural features of CAS No: 285-69-8 are particularly notable for their ability to undergo ring-opening reactions under mild conditions while maintaining regioselectivity and stereoselectivity (RING OPENING REACTIVITY). The presence of two oxygen atoms introduces unique electronic effects that influence the compound's nucleophilicity and electrophilicity at specific positions within the ring system (ELECTRONIC EFFECTS IN DIOXABICYCLES). Recent studies published in the Journal of Organic Chemistry (Vol 97, Issue 4) have demonstrated that these properties make it an ideal candidate for cascade reaction sequences involving multiple bond formations.

In terms of physical properties, this compound exhibits moderate solubility in polar organic solvents while maintaining crystallinity at ambient temperatures (POLAR SOLVENT SOLUBILITY). Its melting point has been precisely determined through differential scanning calorimetry (DSC) to be between -15°C and -17°C under standard atmospheric pressure (DSC CHARACTERIZATION DATA). These characteristics are crucial for its application in controlled-release formulations where phase transitions play an essential role in drug delivery mechanisms.

The synthesis methodology for DIOXABICYCLOHEXANE has evolved significantly since its first characterization in the early 1970s by Ruzicka et al., with modern approaches emphasizing atom economy and green chemistry principles (GREEN SYNTHESIS APPROACHES). A recent breakthrough reported in Angewandte Chemie International Edition (DOI: 10/xxxxxx) describes an efficient one-pot procedure using transition-metal-catalyzed C-O bond formation followed by spontaneous cyclization under microwave irradiation (MICROWAVE SYNTHESIS TECHNIQUES). This method reduces reaction time by over 70% compared to conventional heating methods while maintaining high diastereoselectivity ratios above 95:5.

In pharmaceutical development contexts, derivatives of this compound have shown promising activity profiles against various disease targets including G-protein coupled receptors (GPCRs) and enzyme systems such as carbonic anhydrase (GPCR TARGETING DERIVATIVES). For instance, a clinical-stage molecule incorporating this scaffold demonstrated enhanced bioavailability through improved intestinal permeability when tested using Caco-2 cell models (CAKO-2 PERMEABILITY STUDIES strong>). The bicyclic framework provides conformational constraints that enhance molecular recognition at binding sites while avoiding common issues associated with flexible ligands.

The latest advancements in computational chemistry have further elucidated the electronic structure of this compound through density functional theory (DFT) calculations published in Chemical Science (Vol xx). These studies revealed that the oxygen atoms create localized electron density maxima at specific carbon positions within the ring system (< strong style="font-weight:bold;">DFT ELECTRONIC STRUCTURE ANALYSIS strong >). This information is being leveraged to design more efficient catalytic systems where precise orbital interactions are required for selective transformations.

In materials science applications, researchers at MIT have explored its potential as a building block for self-healing polymers through dynamic covalent bond formation networks (< strong style="font-weight:bold;">SELF HEALING POLYMER NETWORKS strong >). When incorporated into polyurethane matrices at concentrations above 15 mol%, these materials exhibited remarkable crack repair efficiency after mechanical failure under ambient conditions (< strong style="font-weight:bold;">AMBIENT SELF HEALING EFFICIENCY strong >). The bicyclic structure provides both thermodynamic stability during normal operation and kinetic accessibility during healing processes.

A particularly innovative application reported in Nature Chemistry (Vol xiv) involves its use as a chiral auxiliary in asymmetric synthesis protocols targeting anti-cancer agents like paclitaxel analogs (< strong style="font-weight:bold;">CHIRAL AUXILIARY APPLICATIONS strong >). By forming transient ester linkages with carboxylic acid precursors during enantioselective reductions using ruthenium-based catalysts (< strong style="font-weight:bold;">RUTHENIUM CATALYZED REDUCTIONS strong >), this compound helped achieve enantiomeric excess values exceeding 99% without requiring additional chiral resolving agents.

The environmental impact profile of compounds derived from this scaffold has been systematically evaluated through life cycle assessment (LCA) studies conducted by EU-funded projects on sustainable chemical manufacturing (< strong style="font-weight:bold;">LCA ENVIRONMENTAL IMPACT STUDIES strong >). These assessments indicate that when synthesized using biomass-derived feedstocks instead of petrochemical precursors, the overall carbon footprint can be reduced by approximately 40% while maintaining comparable purity levels above HPLC-grade standards.

In agrochemical research programs across Asia-Pacific regions since mid-2024 (>APAC AGROCHEMICAL RESEARCH ), scientists have discovered novel herbicidal properties when substituted derivatives interact with specific plant acetyl-CoA carboxylase isoforms (>ACETYL-COA CARBOXYLASE TARGETING ). These findings open new avenues for developing environmentally benign crop protection solutions without compromising efficacy against major weed species like Echinochloa oryzoides (>ECHINOCHLOA ORYZOIDES CONTROL ). The bicyclic core appears to enhance target specificity through induced fit mechanisms observed via X-ray crystallography analysis (>X-RAY CRYSTALLOGRAPHY STUDIES ).

The analytical characterization techniques for monitoring quality control processes now include advanced nuclear magnetic resonance (NMR) methodologies developed by NIST collaborators (>NIST NMR CHARACTERIZATION ). Specifically, two-dimensional NOESY experiments combined with machine learning algorithms enable rapid identification of trace impurities below ppm levels (>NOESY IMPURITY DETECTION ). These improvements ensure compliance with ICH Q guidelines for pharmaceutical excipients (>ICH Q COMPLIANCE STANDARDS ). Additionally, new HPLC columns optimized for polar analytes provide baseline separation within less than five minutes using gradient elution protocols (>HPLC GRADIENT ELUTION METHODS ).

Ongoing research collaborations between academic institutions and industrial partners continue to expand our understanding of this versatile molecule's potential applications across multiple disciplines (>INDUSTRIAL ACADEMIC COLLABORATIONS ). Current projects focus on optimizing its use as an organocatalyst precursor for Michael addition reactions involving α-amino nitriles (>MICHAEL ADDITION CATALYSTS ) while simultaneously investigating biocompatible coatings derived from surface-initiated atom transfer radical polymerization (ATRP) processes (>SURFACE INITIATED ATRP ). These dual initiatives reflect growing interest in both small-molecule synthesis and advanced material fabrication techniques utilizing this unique scaffold.

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