866398-21-2

Upstream product

• 100863-37-4 1-(3-methoxyphenyl)heptan-1-one 
• 544-97-8 dimethyl zinc(II) 
• 591-31-1 3-methoxy-benzaldehyde 
• 106591-04-2 1-(3-methoxyphenyl)heptan-1-ol 
• 1025867-83-7 C₂₀H₃₅O₅P 
• 87613-50-1 3-(1,1-dimethylheptyl)-5-methoxyphenol 
• 60526-69-4 4-(1,1-dimethylheptyl)-2,6-dimethoxyphenol 
• 60526-81-0 1-(1',1'-dimethylheptyl)-3,5-dimethoxybenzene 
• 628-44-4 2-methyl-2-octanol 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 866398-16-5 trifluoromethanesulfonic acid 4-(1,1-dimethylheptyl)-2,6-dimethoxyphenyl ester 
• 866398-19-8 trifluoromethanesulfonic acid 3-(1,1-dimethylheptyl)-5-methoxyphenyl ester 

Downstream Products

• 181764-33-0 1-bromo-4-(1,1-dimethylheptyl)-2-methoxybenzene 
• 866398-09-6 3-{(7R,8R)-7-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-1,4-dioxaspiro[4,5]dec-8-yl}propan-1-ol 
• 866398-07-4 (7R,8R)-7-[4-(1,1-dimethylheptyl)-2-methoxyphenyl]-8-(2-[1,3]dioxolan-2-ylethyl)-1,4-dioxaspiro[4,5]decane 
• 83002-04-4 CP 55,940 
• 1374219-15-4 2-methoxy-4-(2-methyloctan-2-yl)phenylboronic acid 
• 1374219-24-5 7-(2-methoxy-4-(2-methyloctan-2-yl)phenyl)-1,4-dioxaspiro[4.5]dec-6-en-8-one 
• 1374219-11-0 C₂₄H₃₆O₄ 
• 1374219-10-9 (7S,8S)-7-(2-methoxy-4-(2-methyloctan-2-yl)phenyl)-1,4-dioxaspiro[4.5]decan-8-ol 
• 1374219-25-6 O-(7S,8S)-7-[2-methoxy-4-(2-methyloctan-2-yl)phenyl]-1,4-dioxaspiro[4.5]decan-8-yl S-methyl carbonodithioate 
• 1374219-26-7 O-(1S,2S)-2-[2-methoxy-4-(2-methyloctan-2-yl)phenyl]-4-oxocyclohexyl S-methyl carbonodithioate 
• 1374219-27-8 O-(1S,2S,4R)-4-hydroxy-2-[2-methoxy-4-(2-methyloctan-2-yl)phenyl]cyclohexyl S-methyl carbonodithioate 
• 1374219-29-0 C₂₂H₃₆O₂ 
• 1374219-28-9 C₂₅H₄₀O₂ 
• 1026176-11-3 (1S,4R,5S)-4-[4-(1,1-Dimethyl-heptyl)-2-hydroxy-phenyl]-6,6-dimethyl-bicyclo[3.1.1]heptan-2-one 

Relevant academic research and scientific papers

Enantioselective synthesis of (-)-CP-55940 via ruthenium-catalyzed asymmetric hydrogenation of ketones

A new and efficient catalytic asymmetric synthesis of the potent cannabinoid receptor agonist (-)-CP-55940 has been developed by using ruthenium-catalyzed asymmetric hydrogenation of racemic α-aryl ketones via dynamic kinetic resolution (DKR) as a key step. With RuCl2-SDPs/ diamine [SDPs=7,7'-bis(diarylphophino)-1,1'-spirobiindane] catalysts the asymmetric hydrogenation of racemic α-arylcyclohexanones via DKR provided the corresponding cis-β-arylcyclohexanols in high yields with up to 99.3% ee and >99:1 cis-selectivities. Both ethylene ketal group at the cyclohexane ring and ortho-methoxy group at the phenyl ring of the substrates 6 have little effect on the selectivity and reactivity of the hydrogenations. Based on this highly efficient asymmetric ketone hydrogenation, (-)-CP-55940 was synthesized in 13 steps (the longest linear steps) in 14.6% overall yield starting from commercially available 3-methoxybenzaldehyde and 1,4-cyclohexenedione monoethylene acetal. Copyright

Synthesis and pharmacology of 1-methoxy analogs of CP-47,497

Three 1-methoxy analogs of CP-47,497 (7, 8, and 19) have been synthesized and their affinities for the cannabinoid CB1 and CB2 receptors have been determined. Although these compounds exhibit selectivity for the CB2 recept

Novel, potent THC/anandamide (hybrid) analogs

The structure-activity relationship (SAR) of the end pentyl chain in anandamide (AEA) has been established to be very similar to that of Δ9-tetrahydrocannabinol (Δ9-THC). In order to broaden our understanding of the structural similarities between AEA and THC, hybrid structures 1-3 were designed. In these hybrids the aromatic ring of THC-DMH was linked to the AEA moiety through an ether linkage with the oxygen of the phenol of THC. Hybrid 1 (O-2220) was found to have very high binding affinity to CB1 receptors (Ki = 8.5 nM), and it is interesting to note that the orientation of the side chain with respect to the oxygen in the phenol is the same as in THCs. To further explore the SAR in this series the terminal carbon of the side chain was modified by adding different substituents. Several such analogs were synthesized and tested for their CB1 and CB2 binding affinities and in vivo activity (tetrad tests). The details of the synthesis and the biological activity of these compounds are described.

Expedient synthesis of potent cannabinoid receptor agonist (-)-CP55,940

(Chemical Equation Presented) A stereocontrolled synthesis of (-)-CP55,940, a potent cannabinoid receptor agonist, has been attained using a novel aldolization/retroaldolization interconversion strategy, in which a temporarily generated chiral aldol motif plays essential roles.