92011-93-3

Basic information

• Product Name: 2-<<(tert-butyldimethylsilyl)oxy>methyl>-1,3-cyclohexadiene
• Synonyms: 2-<<(tert-butyldimethylsilyl)oxy>methyl>-1,3-cyclohexadiene
• CAS NO: 92011-93-3
• Molecular Weight: 224.418
• Mol File: 92011-93-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-<<(tert-butyldimethylsilyl)oxy>methyl>-1,3-cyclohexadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-<<(tert-butyldimethylsilyl)oxy>methyl>-1,3-cyclohexadiene(92011-93-3)
• EPA Substance Registry System: 2-<<(tert-butyldimethylsilyl)oxy>methyl>-1,3-cyclohexadiene(92011-93-3)

Safety Data

• Hazardous Substances Data: 92011-93-3(Hazardous Substances Data)

Upstream product

• 312920-44-8 2-bromo-1-(tert-butyldimethylsilyloxymethyl)-3-[2-(tertbutyldimethylsiloxymethyl)cyclohex-2-enyl-1-oxy]-4-methoxy-benzene 
• 1092814-04-4 1-[(tert-butyldimethylsilyl)methyl]-6-chlorocyclohex-1-ene 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 97674-02-7 tributyl(1-ethoxyvinyl)stannane 
• 960-16-7 tributylphenylstannane 
• 22102-40-5 N-(benzo[d][1,3]dioxol-5-ylmethyl)-4-methyl-benzenesulfonamide 
• 335371-10-3 1-tert-butyldimethylsilanyloxymethyl-6-vinyloxycarbonyloxy-1-cyclohexene 
• 2973-58-2 2-bromoisovanillin 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 1024-38-0 N-(2-bromophenyl)-4-methylbenzenesulfonamide 
• 1270092-34-6 2-(tert-butyldimethylsiloxymethyl)cyclohex-2-en-1-yl diethylphosphinate 
• 1270092-33-5 2-(tert-butyldimethylsiloxy)methylcyclohex-2-en-1-yl 2,2,2-trichloroethyl carbonate 
• 784213-45-2 Cyclohexa-1,5-dienecarbonyl chloride 
• 40002-23-1 cyclohexa-1,5-diene-1-carboxylic acid 

Downstream Products

• 92012-03-8 N-benzoyl-3-aza-6-(hydroxymethyl)-2-oxabicyclo<2.2.2>oct-5-ene 
• 92012-04-9 N-benzoyl-3-aza-2-oxabicyclo<2.2.2>oct-5-ene-6-carboxylate 
• 92012-05-0 (1R,2S,7S,8S)-10-Benzoyl-9-oxa-10-aza-tricyclo[6.2.2.0^2,7]dodec-4-ene-7-carboxylic acid methyl ester 
• 92011-94-4 N-benzoyl-3-aza-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxabicyclo<2.2.2>oct-5-ene 
• 92011-95-5 N-benzoyl-3-aza-5-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxabicyclo<2.2.2>oct-5-ene 

Relevant articles and documents

Pd-catalyzed asymmetric allylic amination with BOP ligands and its applications to the synthesis of fused polycyclic alkaloids

Abstract Pd-catalyzed asymmetric allylic amination reaction of piperonylamides and a 2-siloxymethylcyclohexenyl carbonate, using chiral biphenol-based diphosphinite (BOP) ligands gave the corresponding cyclohexenylpiperonylamides in excellent yield and en

Synthesis of chiral biphenol-based diphosphonite ligands and their application in palladium-catalyzed intermolecular asymmetric allylic amination reactions

A library of new 2,2'-bis(diphenylphosphinoyloxy)-1,1'-binaphthyl (binapo)-type chiral diphosphonite ligands was designed and synthesized based on chiral 3,3',5,5',6,6'-hexasubstituted biphenols. These bop ligands have exhibited excellent efficiency in a palladium-catalyzed intermolecular allylic amination reaction, which provides a key intermediate for the total synthesis of Strychnos indole alkaloids with enantiopurities of up to 96% ee. A library of chiral diphosphonite (bop) ligands was synthesized based on chiral hexasubstituted biphenols with fine-tuning capability. Their application for the synthesis of a key intermediate to indole alkaloids through a palladium-catalyzed intermolecular asymmetric allylic amination is reported (TBS=tert-butyldimethylsilyl, TIPS=triisopropylsilyl, dba=dibenzylideneacetone). Copyright

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.