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Usage

InChI:InChI=1/C22H32O2/c1-6-7-8-9-16-13-19(23-5)21-17-12-15(2)10-11-18(17)22(3,4)24-20(21)14-16/h12-14,17-18H,6-11H2,1-5H3/t17-,18-/m1/s1

Upstream product

• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 77982-63-9 nopinone 
• 3410-78-4 cis-DL-Cannabidiol-dimethylether 
• 856767-09-4 4-bromo-2-fluoro-6-methoxy-benzaldehyde 
• 6393-56-2 pentylmagnesium chloride 
• 488787-49-1 Phosphoric acid (3R,4R)-3-(2,6-dimethoxy-4-pentyl-phenyl)-4-(1-methyl-1-triethylsilanyloxy-ethyl)-cyclohex-1-enyl ester diethyl ester 
• 488787-48-0 (R)-3-[(2,6-dimethoxy-4-pentyl)phenyl]-2-iodo-4-[(1-methyl-1-triethylsilyloxy)ethyl]-1-cyclohexanone 
• 488787-50-4 (3R,4R)-3-[(2,6-dimethoxy-4-pentyl)phenyl]-1-methyl-4-[(1-methyl-1-triethylsilyloxy)ethyl]-1-cyclohexene 
• 488787-47-9 (R)-2-iodo-4-[(1-methyl-1-triethylsilyloxy)ethyl]-2-cyclohexen-1-one 
• 488787-46-8 (R)-4-[(1-methyl-1-triethylsilyloxy)ethyl]-2-cyclohexen-1-one 
• 488787-45-7 (R)-4-[(1-hydroxy-1-methyl)ethyl]-2-cyclohexen-1-one 
• 132042-13-8 Acetic acid 1-((R)-4-acetoxy-cyclohex-3-enyl)-1-methyl-ethyl ester 
• 135432-21-2 (R)-4-[(1-acetoxy-1-methyl)ethyl]-2-cyclohexenone 
• 127-91-3 (1R,5R)-(+)-β-pinene 

Downstream Products

• 1972-08-3 dronabinol 

Relevant academic research and scientific papers

Synthesis of Photoswitchable9-Tetrahydrocannabinol Derivatives Enables Optical Control of Cannabinoid Receptor 1 Signaling

The cannabinoid receptor 1 (CB1) is an inhibitory G protein-coupled receptor abundantly expressed in the central nervous system. It has rich pharmacology and largely accounts for the recreational use of cannabis. We describe efficient asymmetric syntheses of four photoswitchable 9-tetrahydrocannabinol derivatives (azo-THCs) from a central building block 3-Br-THC. Using electrophysiology and a FRET-based cAMP assay, two compounds are identified as potent CB1 agonists that change their effect upon illumination. As such, azo-THCs enable CB1-mediated optical control of inwardly rectifying potassium channels, as well as adenylyl cyclase.

Synthesis of (-)-Δ9-trans-tetrahydrocannabinol: Stereocontrol via mo-catalyzed asymmetric allylic alkylation reaction

(Chemical Equation Presented) Δ9-THC is synthesized in enantiomericaly pure form, where all of the stereochemistry is derived from the molybdenum-catalyzed asymmetric alkylation reaction of the extremely sterically congested bis-ortho-substitut

Synthesis of tetrahydrocannabinols based on an indirect 1,4-addition strategy

The synthetic procedure presented for the preparation of the title compounds requires 1,4-addition of bulky cuprates to cyclohexenones and subsequent reaction with electrophiles. However, the enolates generated by BF3·OEt2-assistance suffer from lack of nucleophilicity. To circumvent this problem, we developed an indirect method consisting of the following three steps: (1) iodination of the cyclohexenones at the α position; (2) BF3·OEt2-assisted 1,4-addition of cuprates (Ar2Cu(CN)-Li2, Ar = aryl) followed by quenching the enolates with water; (3) reaction of the α-iodo-β-arylcylohexanones thus formed with EtMgBr to generate magnesium enolates. The enolates thus generated in this way showed a high reactivity toward ClP(O)(OEt)2 to furnish enol phosphates. The aforementioned procedure was also applied to a synthesis of optically active Δ9-tetrahydrocannabinol. In addition, a naphthalene analogue of the latter compound was also synthesized in a similar way.

A Method to Accomplish a 1,4-Addition Reaction of Bulky Nucleophiles to Enones and Subsequent Formation of Reactive Enolates

(matrix presented) BF3-promoted 1,4-addition of bulky aryl groups to α-iodo enones, prepared from the parent enones, afforded β-aryl-α-iodo ketones. Subsequent reaction with EtMgBr furnished the magnesium enolates, which upon reactions with CIP

Synthesis and pharmacological evaluation of ether and related analogues of Δ8-, Δ9-, and Δ9,11-tetrahydrocannabinol

The primary goal of this research was to synthesize a series of ether analogues of the cannabinoid drug class and to evaluate their agonist and antagonist pharmacological properties in either the mouse or the rat. Agonist and antagonist activity was evaluated in mice using a multiple-evaluation procedure (locomotor activity, tail-flick latency, hypothermia, ring immobility) and activity in rats determined in a discriminative stimulus paradigm. Additionally, novel analogues were evaluated for their ability to bind to the THC receptor site labeled by 3H-CP-55,940. None of the cannabinoid analogues were capable of attenuating the effects of Δ9-THC (3 mg/kg) in either the rat (doses up to 10 mg/kg) or in the mouse (doses up to 30 mg/kg). It also appears that the compounds with minimal in vivo activity are not mixed agonist/antagonists. These data would suggest that the phenolic hydroxyl is important for receptor recognition (binding) and in vivo potency. Additionally, cannabinoid methyl ethers previously considered inactive have been found to produce limited activity. Lastly, data suggest that Δ9,11- THC is more potent than previous reports indicated, and does possess pharmacological activity.

A Novel Approach to the Synthesis of the Cannabinoids

The primary cannabinoids have been prepared by a novel sequence of reactions from methyl methacrylate and methyl vinyl ketone