185851-37-0

Basic information

• Product Name: 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylic acid
• Synonyms: 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylic acid
• CAS NO: 185851-37-0
• Molecular Weight: 261.115
• Mol File: 185851-37-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylic acid(185851-37-0)
• EPA Substance Registry System: 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylic acid(185851-37-0)

Safety Data

• Hazardous Substances Data: 185851-37-0(Hazardous Substances Data)

Upstream product

• 185851-22-3 (R)-3-Bromo-2,2,4-trimethyl-5-oxo-cyclohex-3-enecarboxylic acid ((R)-1-phenyl-ethyl)-amide 
• 185851-32-5 (+)-N-(α-methylbenzyl)-3-bromo-2,2,4-trimethylcyclohex-3-ene carboxamide 
• 185851-21-2 (-)-N-(α-methylbenzyl)-3-bromo-2,2,4-trimethylcyclohex-3-ene carboxamide 
• 185851-20-1 3-bromo-2,2,4-trimethylcyclohex-3-ene carbonyl chloride 
• 4773-87-9 3-bromo-2,4-dimethylpenta-1,3-diene 
• 237406-06-3 (-)-N-(α-methylbenzyl)-3-bromo-2,2,4-trimethylcyclohex-3-ene-4-one carboxamide 
• 185851-36-9 C₁₈H₂₁BrN₂O₃ 

Downstream Products

• 237406-08-5 (+)-methyl 3-bromo-5α-hydroxy-2,2,4-trimethylcyclohex-3-ene carboxylate 
• 237406-06-3 (-)-N-(α-methylbenzyl)-3-bromo-2,2,4-trimethylcyclohex-3-ene-4-one carboxamide 
• 185851-38-1 (+)-methyl 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylate 

Relevant articles and documents

Taxane diterpenes 5: Synthesis of the A- and C-rings: An unusual rearrangement of an N-hydroxyimino lactone

Ring A of taxol was synthesized from the bromodiene 5 and acryloyl chloride to give 6, which was resolved by separation of diastereomers 7. Allylic oxidation of 7 gave 8, which on deprotection, esterification and reduction gave 11. Heating 11 followed by reduction and protection gave 13. The C-ring component was made using asymmetric Birch reduction methodology combined with standard functional group manipulations to give 28. Combining 13 and 28 gave 29, which was converted into 33. Thermolysis of 33 did not generate a nitrile oxide but rather ionized to an oxydienyl cation, eventually leading to 34.