18917-78-7

Upstream product

• 122903-50-8 3-(3,5-Dimethoxyphenyl)-2-butyl methanesulfonate 
• 412033-49-9 2-cyano-2-(3,5-dimethoxy-phenyl)-propionic acid ethyl ester 
• 122903-49-5 3-(3,5-Dimethoxyphenyl)-2-butanol 
• 122903-51-9 1-(3,5-Dimethoxyphenyl)ethyl chloride 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 14950-55-1 rac-1-(3,5-dimethoxyphenyl)ethan-1-ol 
• 35051-96-8 2-(3,5-dimethoxyphenyl)propanenitrile 
• 18917-77-6 (3,5-dimethoxyphenyl)acetone 
• 74-88-4 methyl iodide 
• 122903-49-5 3-(3,5-Dimethoxyphenyl)-2-butanol 
• 4670-10-4 (3,5-dimethoxyphenyl)acetic acid 
• 15601-07-7 2-(3,5-dimethoxyphenyl)acetyl chloride 

Downstream Products

• 122903-55-3 3-(3,5-Dimethoxyphenyl)-2-deuterio-2-butanol 
• 122946-54-7 3-(3,5-Dimethoxyphenyl)-2-deuterio-2-butyl methanesulfonate 
• 122946-54-7 3-(3,5-Dimethoxyphenyl)-2-deuterio-2-butyl methanesulfonate 
• 195001-62-8 6-(3',5'-dimethoxyphenyl)-3-methoxy-6-methylcyclohex-2-enone 
• 170753-26-1 4-(3',5'-dimethoxyphenyl)-4-methyl-3-vinylcyclohex-2-enone 

Relevant academic research and scientific papers

Use of conjugated dienones in cyclialkylations: Total syntheses of arucadiol, 1,2-didehydromiltirone, (±)-hinokione, (±)-nimbidiol, sageone, and miltirone

Functionalized hydrophenanthrenes can be prepared using a cyclialkylation-based strategy. These annulations are highly dependent on the directing effects of the arene substitutents and on conformational considerations. The utility of this methodology was featured in the syntheses of six diterpenoids.

Photochemical Transformation. 48. The Nonconcertedness of Nucleofuge Loss and anti-Aryl Migration in Photochemical Wagner-Meerwein Rearrangements

Preparation of the two diastereomeres of 3-(3,5-dimethoxyphenyl)-2-butanol and of their 2-deuterio analogues has been carried out.When the methanesulfonate esters of the diastereomers were solvolyzed by heating at reflux in 50percent aqueous methanol, the resulting alcohols and methyl ethers were formed with complete retention of diastereomeric identity and without measurable hydride migration to give the 2-aryl-2-butyl isomer.Similar treatment of the methanesulfonates of the deuterio analogues gave complete deuterium scrambling, that is, gave equal mixtures of 3-aryl-2-deuterio -2-butyl and 3-aryl-3-deuterio-2-butyl derivatives.These results of ground-state solvolyses are consistent with aryl participation coincident with nucleofuge loss, with bridged phenonium ions as sole intermediates.On the other hand, irradiations of the methanesulfonates with 300-nm light in the same solvent gave photosolvolysis with considerable diastereomeric mixing, although again complete deuterium scrambling was observed here as well.In addition, significant amounts of 2-aryl-2-butanol were formed.The excited-state results require a much more complicated reaction course than the ground-state results, probably involving syn-hydrogen migration to give the tertiary alcohol, along one path, and requiring that the observed aryl migrations, along another path, occur later than, rather than concerted with, nucleofuge loss.