99285-26-4

Basic information

• Product Name: N-(E-2,6-heptanedienoyl)-l-ephedrine
• Synonyms: N-(E-2,6-heptanedienoyl)-l-ephedrine
• CAS NO: 99285-26-4
• Molecular Weight: 273.375
• Mol File: 99285-26-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(E-2,6-heptanedienoyl)-l-ephedrine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(E-2,6-heptanedienoyl)-l-ephedrine(99285-26-4)
• EPA Substance Registry System: N-(E-2,6-heptanedienoyl)-l-ephedrine(99285-26-4)

Safety Data

• Hazardous Substances Data: 99285-26-4(Hazardous Substances Data)

Upstream product

• 492-41-1 (1R,2S)-norephedrine 
• 99285-25-3 (2E)-Hepta-2,6-dienoic acid chloride 
• 821-09-0 n-Pent-4-enyl alcohol 
• 2100-17-6 4-pentenal 
• 38867-17-3 (2E)-hepta-2,6-dienoic acid 

Downstream Products

• 99285-28-6 N-(3-isopropenyl-6-heptenoyl)-l-ephedrine 
• 38746-47-3 (R)-5,5-dimethyl-4-(3-oxo-butyl)-dihydro-furan-2-one 
• 80408-87-3 (+)-5,5-dimethyl-4-(3-oxobutyl)tetrahydrofuran-2-one 
• 99285-31-1 (S)-3-(4-Methoxy-phenyl)-hept-6-enoic acid ((S)-1-naphthalen-1-yl-ethyl)-amide 
• 99285-27-5 N-(3-p-methoxyphenyl-6-heptenoyl)-l-ephedrine 

Relevant articles and documents

Asymmetric synthesis towards (3Z,6R)-3-methyl-6-isopropenyl-3,9-decadien-1-yl acetate, a component of the California red scale pheromone

The key chiral synthons, (R)-3-isopropenyl-6-heptenoic acid and (R)-3-isopropenyl-6-heptenal, needed for the synthesis of (3Z,6R)-3-methyl-6-isopropenyl-3,9-decadien-1-yl acetate, a component of the sex pheromone of the California red scale, Aonidiella aurantii, have been prepared by asymmetric synthesis.The chiral acid was synthesized in 86percent ee by an asymmetric 1,4-addition of isopropenylmagnesium bromide to the l-ephedrine amide derived from (E)-2,6-heptadienoic acid, followed by base hydrolysis.Acid hydrolysis gave the chiral 3-(3-buten-1-yl)-4,4-dimethylbutyrolactone.The chiral aldehyde was prepared in greater than 99percent ee by an asymmetric 1,4-addition of isopropenylmagnesium bromide to the imine derived from (S)-(+)-tert-butyl 2-amino-3,3-dimethylbutyrate and (E)-2,6-heptadienal.The 1,4-addition reactions of n-butyllithium or isopropenyllithium to (4S,5S)-(+)-2--4-methoxymethyl-5-phenyl-2-oxazoline gave the addition products, and sequential mild hydrolysis and reduction of these adducts yielded chiral 3-n-butyl-6-hepten-1-ol for the former adduct but a mixture of products was obtained from the latter adduct.