488787-51-5

Basic information

• Product Name: (3R,4R)-3-[(2-hydroxy-6-methoxy-4-pentyl)phenyl]-1-methyl-4-[(1-methyl-1-triethylsilyloxy)ethyl]-1-cyclohexene
• Synonyms: (3R,4R)-3-[(2-hydroxy-6-methoxy-4-pentyl)phenyl]-1-methyl-4-[(1-methyl-1-triethylsilyloxy)ethyl]-1-cyclohexene
• CAS NO: 488787-51-5
• Molecular Weight: 346.51
• Mol File: 488787-51-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3R,4R)-3-[(2-hydroxy-6-methoxy-4-pentyl)phenyl]-1-methyl-4-[(1-methyl-1-triethylsilyloxy)ethyl]-1-cyclohexene(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-3-[(2-hydroxy-6-methoxy-4-pentyl)phenyl]-1-methyl-4-[(1-methyl-1-triethylsilyloxy)ethyl]-1-cyclohexene(488787-51-5)
• EPA Substance Registry System: (3R,4R)-3-[(2-hydroxy-6-methoxy-4-pentyl)phenyl]-1-methyl-4-[(1-methyl-1-triethylsilyloxy)ethyl]-1-cyclohexene(488787-51-5)

Safety Data

• Hazardous Substances Data: 488787-51-5(Hazardous Substances Data)

Upstream product

• 3411-09-4 (E)-4-(2,6-dimethoxy-4-pentylphenyl)but-3-en-2-one 
• 7663-54-9 2',6'-dimethoxy-1'-((E)-3-methylbuta-1,3-dienyl)-4'-pentylbenzene 
• 3410-84-2 2,6-dimethoxy-4-pentylbenzaldehyde 
• 1310045-84-1 1-(2',6'-dimethoxy-5-methyl-4'-pentyl-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)ethanone 
• 1310045-80-7 (2''S)-N-{(1E)-1-[(1R,2R)-2-(2',6'-dimethoxy-4'-pentylphenyl)-4-methylcyclohex-3-en-1-yl]ethylidene}-2''-(methoxymethyl)pyrrolidin-1''-amine 
• 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 
• 77982-63-9 nopinone 
• 930598-01-9 2-[1-(2,6-dimethoxy-4-pentylphenyl)allyl]-5-methyl-5-hexenoic acid methyl ester 
• 930597-95-8 methyl (1R,2R)-2',6'-dimethoxy-5-methyl-4'-pentyl-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-carboxylate 
• 930598-04-2 2-(2,6-dimethoxy-4-pentylphenyl)-4-methyl-cyclohex-3-enecarboxylic acid methyl ester 
• 930597-96-9 dimethyl [1-(2,6-dimethoxy-4-pentylphenyl)allyl]malonate 

Downstream Products

• 1972-08-3 dronabinol 
• 36403-68-6 D1,2-Tetrahydrocannabinol methyl ether 

Relevant articles and documents

High-pressure access to the Δ9-cis - And Δ9-trans-tetrahydrocannabinols family

Diels-Alder reactions of a range of 1-(alkoxy/alkyl-substituted phenyl)buta-1,3-dienes with methyl vinyl ketone and methyl acrylate carried out in ethanol as the reaction medium under 9 kbar pressure were investigated. The use of high pressure as the activating method of the Diels-Alder reactions allows the efficient and endodiastereoselective generation of a series of cis-cyclohexenyl-benzene cycloadducts, which are selectively converted into their trans-epimers. The cis-cyclohexenyl-benzenes and trans-cyclohexenyl- benzenes produced are useful precursors for accessing substituted privileged cis-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene and trans-6a,7,8,10a-tetrahydro- 6H-benzo[c]chromene skeletons. The total syntheses of Δ9-cis- tetrahydrocannabinol (THC) and Δ9-trans-THC, through the use of selected Diels-Alder adducts, are described. Finally, a route for obtaining Δ9-trans-THC in both enantiomeric pure forms based on the (S)-(-)-1-amino-2-(methoxymethyl)pyrrolidine (SAMP)-hydrazone method is also reported.

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.