831-78-7

Upstream product

• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 717-94-2 3-(3,5-dimethoxyphenyl)propionic acid 
• 16909-11-8 3-(3,5-dimethoxyphenyl)acrylic acid 
• 730-01-8 2-(3',5'-Dimethoxyphenyl)-ethane-1,1-dicarboxylic acid 
• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 886-51-1 Methyl 3-(3',5'-dimethoxyphenyl)propionate 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 20767-04-8 (E)-3,5-dimethoxycinnamic acid 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 29577-41-1 3-(3,5-dimethoxyphenyl)-2-propyn-1-ol 
• 60319-09-7 3,5-dimethoxyphenyl trifluoromethanesulfonate 
• 500-99-2 3,5-dimethoxyphenol 
• 1080-05-3 3-(3,5-dimethoxyphenyl)-1-propanol 

Downstream Products

• 91555-31-6 4-(3,5-dimethoxyphenyl)butanoic acid 
• 889-24-7 5-(3,5-dimethoxyphenyl)pentanoic acid 
• 256510-53-9 1-(3,5-dimethoxyphenyl)-4-octyne 
• 1586815-06-6 benzyl 6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate 
• 83035-49-8 dl-(Z)-2-[6-(3,5-dimethoxyphenyl)-2-methyl-3-hexenyl]-3-methyl-2-cyclopentenone 
• 202654-80-6 1-(3,5-dimethoxyphenyl)octane-5,7-dione 

Relevant academic research and scientific papers

First synthesis of dopamine and rotigotin analogue 2-amino-6,8-dimethoxy-1, 2,3,4-tetrahydronaphthalene

The title compound was synthesized starting from 3-(3,5-dimethoxyphenyl) acrylic acid in 11 steps with 30% total yield. The reaction sequence hydrogenation of acrylic acid, reduction of acid to alcohol derivative with LiAlH4, reaction of alcohol with CBr4/PPh3, substitution reaction of alkyl halide to nitrile derivative with NaCN, hydrolysis of nitrile with NaOH, cyclization reaction of acid with PPA to give 1-tetralone, α-carboxylation of tetralone with Me2CO 3 in the presence of NaH, reduction of ketone group with Et 3SiH, hydrolysis of ester, Curtius rearrangement of acid with diphenylphosphoryl azide followed by conversion to carbamate, and finally hydrogenolysis of carbamate afforded 2-amino-6,8-dimethoxy-1,2,3,4- tetrahydronaphthalene hydrogen chloride salt.

Development of agonists, partial agonists and antagonists in the Δ8- tetrahydrocannabinol series

Synthetic sequences were developed (Schemes 1 to 6) for the syntheses of various Δ8-THC analogs with either a rigid acetylenic linkage or a cis- double bond in different positions in the side chain. Various alkyne and cis- ene-Δ8-THC

Radical-mediated cyclisation of ω-aryl-β-dicarbonyl compounds to tetrahydrobenzocyclohepten-6-ones, hexahydrobenzocycloocten-6-ones and naphthalen-2(1H)-ones

Manganese(III) acetate in acetic acid promotes efficient radical-mediated oxidative cyclisation of ε-aryl-β-dicarbonyl and Z-γ,δ-unsaturated δ-aryl-β-dicarbonyl compounds carrying electron-releasing groups in the aromatic ring, forming 6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ones and naphthalen-2(1H)-ones, respectively. The process is accompanied by secondary acetoxylation at the activated benzylic position of the initial cyclisation products, and is exemplified by the conversions of the ε- and δ-aryl-β-dicarbonyl compounds 6 and 11 into the benzocycloheptenone 18 and the naphthalenone 21, respectively. Application of the oxidation to the formation of 8-membered hexahydro- and tetrahydro-benzocycloocten-6-ones 19 and 22 from ζ-aryl-β-dicarbonyl and Z-γ,δ-unsaturated ζ-aryl-β-dicarbonyl compounds is limited by low reactivity, and in the latter case, by radical rearrangement followed by cyclisation to a tetralin.