80595-59-1

Basic information

• Product Name: bromoacetic acid (-)-8-phenylmenthol ester
• Synonyms: bromoacetic acid (-)-8-phenylmenthol ester
• CAS NO: 80595-59-1
• Molecular Weight: 353.299
• Mol File: 80595-59-1.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: bromoacetic acid (-)-8-phenylmenthol ester(CAS DataBase Reference)
• NIST Chemistry Reference: bromoacetic acid (-)-8-phenylmenthol ester(80595-59-1)
• EPA Substance Registry System: bromoacetic acid (-)-8-phenylmenthol ester(80595-59-1)

Safety Data

• Hazardous Substances Data: 80595-59-1(Hazardous Substances Data)

Upstream product

• 129180-87-6 (-)-8-phenylmenthol phenylcarbamate 
• 57707-91-2 (5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanol 
• 97371-54-5 (-)-(2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanon 
• 89-82-7 pulegone 
• 65253-04-5 (-)-8-phenylmenthol 
• 598-21-0 2-Bromoacetyl bromide 
• 79-08-3 bromoacetic acid 
• 22118-09-8 2-bromoacetyl chloride 

Downstream Products

• 179928-01-9 (S)-3-(4-Benzyloxy-phenyl)-3-(4-fluoro-phenylamino)-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 910803-61-1 8-phenylmenthyl (1,3-benzothiazol-2-ylsulfanyl)acetate 
• 1004759-68-5 N-benzyl-N,N-dimethyl-N-[(-)-8-phenylmenthoyloxycarbonylmethyl]ammonium bromide 
• 1004759-63-0 N-(4'-tert-butoxycarbonylbenzyl)-N,N-dimethyl-N-[(-)-8-phenylmenthoyloxycarbonylmethyl]ammonium bromide 
• 1004759-77-6 N,N-dimethyl-N-[(-)-8-phenylmenthoyloxycarbonylmethyl]-N-(2'-trifluoromethylbenzyl)ammonium bromide 
• 1004759-92-5 N,N-dimethyl-N-(4'-methoxybenzyl)-N-[(-)-8-phenylmenthoyloxycarbonylmethyl]ammonium bromide 
• 1004759-76-5 N-(2'-cyanobenzyl)-N,N-dimethyl-N-[(-)-8-phenylmenthoyloxycarbonylmethyl]ammonium bromide 
• 1004759-81-2 N,N-dimethyl-N-[(-)-8-phenylmenthoyloxycarbonylmethyl]-N-(3'-trifluoromethylbenzyl)ammonium bromide 
• 1004759-64-1 N,N-dimethyl-N-(4'-metoxycarbonylbenzyl)-N-[(-)-8-phenylmenthoyloxycarbonylmethyl]ammonium bromide 
• 1004759-67-4 N,N-dimethyl-N-[(-)-8-phenylmenthoyloxycarbonylmethyl]-N-(4'-trifluoromethylbenzyl)ammonium bromide 
• 1004759-66-3 N-(4'-benzoylbenzyl)-N,N-dimethyl-N-[(-)-8-phenylmenthoyloxycarbonylmethyl]ammonium bromide, monohydrate 
• 1004759-80-1 N-(3'-cyanobenzyl)-N,N-dimethyl-N-[(-)-8-phenylmenthoyloxycarbonylmethyl]ammonium bromide 
• 1004759-65-2 N-(4'-cyanobenzyl)-N,N-dimethyl-N-[(-)-8-phenylmenthoyloxycarbonylmethyl]ammonium bromide 
• 1088482-11-4 N-allyl-N,N-dimethyl-N-[(-)-8-phenylmenthyloxycarbonylmethyl]ammonium bromide 

Relevant articles and documents

Asymmetric Wittig reaction of chiral arsonium ylides - I. Asymmetric olefination of 4-substituted cyclohexanones

Asymmetric Wittig-type olefination of 4-substituted cyclohexanones with chiral ligand-modified stable arsonium ylides has been examined. The 8-phenylmenthol-derived chiral arsonium ylide of 4 reacted with prochiral ketones 9a-d at -15°C to give the 4-substituted cyclohexylideneacetates 11a-d in 58-69% yield and in up to 80% diastereomeric excess (de).

Exceptionally mild, high-yield synthesis of α-fluoro acrylates

Novel achiral and chiral alkyl α-(1,3-benzothiazol-2-ylsulfonyl)- α-fluoroacetates can be readily synthesized by metalation-fluorination of (1,3-benzothiazol-2-ylsulfonyl)acetates. DBU-mediated condensations of these fluorinated synthons with aldehydes proceed in a facile manner at 0 °C or at room temperature giving high yields of α-fluoro acrylates. Ketones are unreactive under these conditions. The presence of fluorine renders the synthon substantially more reactive compared to the unfluorinated analogue. Reactivity of α-(1,3-benzothiazol-2-ylsulfonyl)-α-fluoroacetate and the Horner-Wadsworth-Emmons reagent (EtO)2P(O)CHFCOOEt has also been compared.

Remarkable examples of double diastereodifferentiation: Application to the eudistomin and eudistomidin alkaloids

Nucleophilic addition of chiral enolates 1 and ent-1 with chiral iminium ion 2a occur with total stereochemical control.