82078-77-1

Basic information

• Product Name: Bicyclo[3.1.1]hept-3-ene-2,2-diol, 6,6-dimethyl-, diacetate, (1R,5R)-
• CAS NO: 82078-77-1
• Molecular Formula: C13H18O4
• Molecular Weight: 238.284
• Mol File: 82078-77-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 277.9±40.0 °C(Predicted)
• Density: 1.14±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Bicyclo[3.1.1]hept-3-ene-2,2-diol, 6,6-dimethyl-, diacetate, (1R,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[3.1.1]hept-3-ene-2,2-diol, 6,6-dimethyl-, diacetate, (1R,5R)-(82078-77-1)
• EPA Substance Registry System: Bicyclo[3.1.1]hept-3-ene-2,2-diol, 6,6-dimethyl-, diacetate, (1R,5R)-(82078-77-1)

Safety Data

• Hazardous Substances Data: 82078-77-1(Hazardous Substances Data)

Upstream product

• 38651-65-9 (1R,5S)-(+)-nopinone 
• 28239-05-6 (-)-nopinone enol acetate 
• 546-67-8 lead(IV) tetraacetate 

Downstream Products

• 182509-23-5 (1R,4R,5R)-4-(2,6-dihydroxy-4-(2-methyloctan-2-yl)phenyl)-6,6-dimethylbicyclo[3.1.1]heptan-2-one 
• 35408-03-8 (+)-apoverbenone 
• 1236197-83-3 C₂₁H₂₄O₇ 

Relevant articles and documents

Novel Labelled Cannabinergic Ligands and Related Analogs

Novel cannabinoid ligands represented by the general formulas I, II, and III and methods for preparation and use within which one or more of a fluorescent ligand, nitroxide spin label, metal chelate, biotin moiety, or group with enhanced polarity may be incorporated. The compounds can bind to and modulate the cannabinoid CB1 and CB2 receptors and thereby considered specific ligands for these receptors. Some of the disclosed compounds that bind to cannabinoid CB1 and CB2 receptors can exhibit tight or irreversible binding characteristics for these receptors. Due to the presence of the imaging/diagnostic and/or therapeutic functional groups including fluorescent groups, nitroxide spin labels, metal chelates, biotin moieties, and groups with enhanced polarity, the disclosed compounds may be useful as imaging/diagnostic tools and/or therapeutic agents.

A concise methodology for the synthesis of (-)-Δ9-tetrahydrocannabinol and (-)-Δ9-tetrahydrocannabivarin metabolites and their regiospecifically deuterated analogs

The availability of tetrahydrocannabinols (Δ9-THC), tetrahydrocannabivarins (Δ9-THCV), and their metabolites in both their undeuterated and deuterated forms is critical for the analysis of biological and toxicological samples. We report here a concise methodology for the syntheses of (-)-Δ9-THC and (-)-Δ9-THCV metabolites in significantly improved overall yields using commercially available starting materials. Our approach allowed us to obtain the key intermediates (6aR,10aR)-9-nor-9-oxo-hexahydrocannabinols in four steps from (+)-(1R)-nopinone. This was followed by an optimized Shapiro reaction to give the (-)-11-nor-9-carboxy-metabolites, which were converted to their respective (-)-11-hydroxy analogs. The synthetic sequence involves a minimum number of steps, avoids undesirable oxidative conditions, and incorporates the costly deuterated resorcinols near the end of the synthetic sequence. This methodology enabled us to synthesize eight regiospecifically deuterated (-)-Δ9-THC and (-)-Δ9-THCV metabolites in a preparative scale and high optical purity without deuterium scrambling or loss.