374782-84-0

Basic information

• Product Name: 1-Diazo-4-((R)-1,3,3-trimethyl-2-methylene-cyclohexyl)-butan-2-one
• Synonyms: 1-Diazo-4-((R)-1,3,3-trimethyl-2-methylene-cyclohexyl)-butan-2-one
• CAS NO: 374782-84-0
• Molecular Weight: 234.341
• Mol File: 374782-84-0.mol

Chemical Properties

• CAS DataBase Reference: 1-Diazo-4-((R)-1,3,3-trimethyl-2-methylene-cyclohexyl)-butan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Diazo-4-((R)-1,3,3-trimethyl-2-methylene-cyclohexyl)-butan-2-one(374782-84-0)
• EPA Substance Registry System: 1-Diazo-4-((R)-1,3,3-trimethyl-2-methylene-cyclohexyl)-butan-2-one(374782-84-0)

Safety Data

• Hazardous Substances Data: 374782-84-0(Hazardous Substances Data)

Upstream product

• 472-66-2 (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde 
• 123643-44-7 4-(2',6',6'-trimethyl-1'-cyclohexenyl)-1-buten-3-ol 
• 123643-43-6 3-((S)-1,3,3-Trimethyl-2-methylene-cyclohexyl)-propionaldehyde 
• 123643-45-8 ethyl 4-(2',6',6'-trimethyl-1'-cyclohexenyl)-2-butenoate 
• 123643-47-0 [(2R,3R)-3-(2,6,6-Trimethyl-cyclohex-1-enylmethyl)-oxiranyl]-methanol 
• 123643-48-1 (2S,3R)-2-Iodomethyl-3-(2,6,6-trimethyl-cyclohex-1-enylmethyl)-oxirane 
• 123643-46-9 4-(2',6',6'-trimethyl-1'-cyclohexenyl)-2-butenol 
• 86558-54-5 2-((E)-2-Methoxy-vinyl)-1,3,3-trimethyl-cyclohexene 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 374782-81-7 ((R)-6,8,8-Trimethyl-7-methylene-1,4-dithia-spiro[4.5]dec-6-yl)-acetic acid methyl ester 
• 374782-78-2 (+)-methyl 3-[(1R)-1,3,3-trimethyl-2-methylenecyclohexyl]propionate 
• 374782-83-9 1-Diazo-3-((R)-1,3,3-trimethyl-2-methylene-cyclohexyl)-propan-2-one 
• 374782-82-8 ((R)-1,3,3-Trimethyl-2-methylene-cyclohexyl)-acetic acid 
• 374782-79-3 (-)-methyl (1R)-1,3,3-trimethyl-2-methylenecyclohexane-1-acetate 

Relevant articles and documents

An enantiospecific approach to tricyclic sesquiterpenes mayurone and thujopsenes

An enantiospecific approach to mayurone and thujopsenes, sesquiterpenes containing three contiguous quaternary carbon atoms, starting from (R)-carvone (8), is described. (S)-3,4,4-Trimethylcarvone (7), obtained from (R)-carvone, was transformed into the bicyclo[2.2.2]octanone 13 via regioselective intramolecular alkylation of the allyl bromide 11. Regioselective ozonolysis and Criegee fragmentation of the bicyclic ketone 13 furnished the keto ester 14. Reductive deoxygenation followed by one-carbon homologation transformed the keto ester 19 into the ester 6. Intramolecular cyclopropanation of the diazo ketone 25, derived from the acid 5, furnished (-)dihydromayurone (4), thus constituting a formal enantiospecific synthesis of mayurone and thujopsenes.

Enantiocontrolled synthesis of quaternary carbon centers via anionic oxy-cope rearrengement: An efficient synthesis of (+)-dihydromayurone

(+)-Dihydromayurone (1) was enantioselectively synthesized from β-cyclocitral (7). The key step in the synthesis involved anionic oxy-Cope of allylic alcohol 6 to aldehyde 5. Efficient transfer of chirality from the secondary allylic alcohol center to the quaternary carbon center was observed vai chairlike transition state with the equatorial oxyanionic bond.