482374-40-3

Basic information

• Product Name: [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]methanol
• Synonyms: [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]methanol
• CAS NO: 482374-40-3
• Molecular Weight: 387.271
• Mol File: 482374-40-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]methanol(482374-40-3)
• EPA Substance Registry System: [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]methanol(482374-40-3)

Safety Data

• Hazardous Substances Data: 482374-40-3(Hazardous Substances Data)

Upstream product

• 621-59-0 isovanillin 
• 312920-40-4 (S)-(-)-methyl 6-(2-bromo-3-formyl-6-methoxyphenoxy)-cyclohex-1-enecarboxylate 
• 312920-36-8 methyl 6-(2,2,2-trichloroethoxycarbonyloxy)cyclohex-1-enoate 
• 2973-58-2 2-bromoisovanillin 
• 865780-25-2 methyl 6-hydroxy-cyclohex-1-enecarboxylate 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 869369-38-0 [(S)-6-(2-Bromo-3-dimethoxymethyl-6-methoxy-phenoxy)-cyclohex-1-enyl]-acetonitrile 
• 57-27-2 MORPHIN 
• 76-57-3 codeine 
• 357-70-0 Galantamine 
• 1668-85-5 (-)-epigalanthamine 
• 482374-41-4 [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]acetonitrile 

Relevant articles and documents

Divergent enantioselective synthesis of (-)-galanthamine and (-)-morphine

An efficient divergent synthetic strategy for the synthesis of the opiate and amaryllidaceae alkaloids emerges by employing a Pd-catalyzed asymmetric allylic alkylation (AAA) to set the stereochemistry. Three generations of syntheses of galanthamine are discussed in detail with particular focus on the scope of the palladium-catalyzed AAA reactions and intramolecular Heck reactions. The pivotal tricyclic intermediate is available in six steps from 2-bromovanillin and the monoester of methyl 6-hydroxycyclohexene-1-carboxylate. This intermediate requires only two steps to convert to (-)-galanthamine. Using a Heck vinylation, we found that the fourth ring of codeine/morphine could be formed. The final ring formation involves a novel visible light-promoted hydroamination. Thus, six steps are required to convert the pivotal tricyclic intermediate into codeine, which has been demethylated in high yield to morphine.