225779-46-4

Basic information

• Product Name: 6-methoxycarbonyloxycyclohex-1-enecarboxylic acid methyl ester
• Synonyms: 6-methoxycarbonyloxycyclohex-1-enecarboxylic acid methyl ester
• CAS NO: 225779-46-4
• Molecular Weight: 214.218
• Mol File: 225779-46-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 6-methoxycarbonyloxycyclohex-1-enecarboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methoxycarbonyloxycyclohex-1-enecarboxylic acid methyl ester(225779-46-4)
• EPA Substance Registry System: 6-methoxycarbonyloxycyclohex-1-enecarboxylic acid methyl ester(225779-46-4)

Safety Data

• Hazardous Substances Data: 225779-46-4(Hazardous Substances Data)

Upstream product

• 865780-25-2 methyl 6-hydroxy-cyclohex-1-enecarboxylate 
• 79-22-1 methyl chloroformate 

Downstream Products

• 932743-56-1 (6S)-6-(4-methoxybenzylamino)cyclohex-1-enecarboxylic acid methyl ester 
• 1041370-21-1 (R)-2-methoxycarbonyl-2-cyclohexen-1-ylmalonic acid dibenzyl ester 
• 1342302-07-1 3-{(6S)-6-[tert-butoxycarbonyl(4-methoxybenzyl)amino]cyclohex-1-enyl}-3-oxopropionic acid allyl ester 
• 1342302-24-2 3-{(S)-6-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]cyclohex-1-enyl}-3-oxopropionic acid methyl ester 
• 1342302-06-0 3-{(6S)-6-[tert-butoxycarbonyl(4-methoxybenzyl)amino]cyclohex-1-enyl}-3-hydroxypropionic acid allyl ester 
• 1342302-23-1 3-{(6S)-6-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]cyclohex-1-enyl}-3-hydroxypropionic acid methyl ester 
• 1342302-05-9 (1S)-(2-formylcyclohex-2-enyl)(4-methoxybenzyl)carbamic acid tert-butyl ester 
• 1342302-22-0 C₂₀H₂₉NO₄ 
• 1342302-04-8 (6S)-6-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]cyclohex-1-enecarboxylic acid methyl ester 
• 1342302-08-2 (2S,8aS)-1-(4-methoxybenzyl)-2-propyl-2,3,6,7,8,8a-hexahydro-1H-quinolin-4-one 
• 1342302-19-5 (2S,8aS)-4-hydroxy-1-(4-methoxybenzyl)-2-phenyl-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester 
• 1342302-18-4 (2S,8aS)-4-hydroxy-2-isopropyl-1-(4-methoxybenzyl)-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester 
• 1342302-15-1 (2S,8aS)-4-hydroxy-1-(4-methoxybenzyl)-2-methyl-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester 
• 932743-60-7 C₂₃H₃₀N₂O₄ 

Relevant articles and documents

Pd-catalyzed asymmetric allylic alkylation of 2-substituted cycloalkenyl carbonates using a chiral diaminophosphine oxide: (S,RP)-Ph-DIAPHOX

A Pd-catalyzed asymmetric allylic alkylation of 2-substituted cycloalkenyl carbonates using a chiral diaminophosphine oxide is described. Asymmetric allylic substitution of various cyclic substrates proceeded using 5 mol % of Pd catalyst, 10 mol % of (S,R

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.