187083-78-9

Upstream product

• 625-38-7 but-3-enoic acid 
• 192182-54-0 3,5-dimethoxyphenylboronic acid 
• 187083-92-7 (E)-3-(3,5-Dimethoxy-phenyl)-but-2-enoic acid ethyl ester 
• 39151-19-4 1-(3,5-dimethoxyphenyl)ethan-1-one 
• 147700-59-2 E-3-(3,5-dimethoxyphenyl)-2-butenoic acid 
• 147700-59-2 3,5-Dimethoxycinnamic Acid 

Downstream Products

• 220169-70-0 (R)-3-(3,5-dimethoxyphenyl)-1-butanol tosylate 
• 220169-97-1 (S)-3-(3,5-dimethoxyphenyl)-1-butanol tosylate 
• 187083-79-0 Toluene-4-sulfonic acid 3-(3,5-dimethoxy-phenyl)-butyl ester 
• 187084-02-2 (S)-3-(3,5-Dimethoxy-phenyl)-butyric acid 
• 187083-93-8 (R)-3-(3,5-Dimethoxy-phenyl)-butyric acid 
• 187084-01-1 (R)-3-(3,5-Dimethoxy-phenyl)-butyramide 
• 65511-91-3 3-(3,5-dimethoxyphenyl)-1-butanol 
• 187084-17-9 N-((1S)-1-phenylethyl)-(3R)-3-(3,5-dimethoxyphenyl)butanamide 
• 187084-18-0 N-((1S)-1-phenylethyl)-(3S)-3-(3,5-dimethoxyphenyl)butanamide 

Relevant academic research and scientific papers

Ligand-Controlled Regiodivergence in Nickel-Catalyzed Hydroarylation and Hydroalkenylation of Alkenyl Carboxylic Acids**

A nickel-catalyzed regiodivergent hydroarylation and hydroalkenylation of unactivated alkenyl carboxylic acids is reported, whereby the ligand environment around the metal center dictates the regiochemical outcome. Markovnikov hydrofunctionalization products are obtained under mild ligand-free conditions, with up to 99 % yield and >20:1 selectivity. Alternatively, anti-Markovnikov products can be accessed with a novel 4,4-disubstituted Pyrox ligand in excellent yield and >20:1 selectivity. Both electronic and steric effects on the ligand contribute to the high yield and selectivity. Mechanistic studies suggest a change in the turnover-limiting and selectivity-determining step induced by the optimal ligand. DFT calculations reveal that in the anti-Markovnikov pathway, repulsion between the ligand and the alkyl group is minimized (by virtue of it being 1° versus 2°) in the rate- and regioselectivity-determining transmetalation transition state.

Side chain methyl analogues of Δ8-THC

The synthesis of both side chain epimers of 1'- (4), 2'- (5), 3'-methyl- (6) and 4'-methyl-Δ8-tetrahydrocannobinol (7) has been carried out. The synthetic approach entailed the acid catalyzed condensation of the appropriate substituted resorcinol with menthadienol to provide the Δ8-THC analogue. Both isomers of 1'- (4) and 2'-Δ8-THC (5) were more potent than Δ8-THC, both in vitro and in vivo. The 3'-methyl isomers (6) were approximately equal in potency to Δ8-THC, and 4'-methyl-Δ8-THC was less potent. There was relatively little difference in potency between the epimers of 4, 5, and 6.