17559-40-9

Basic information

• Product Name: (1S,2R)-1-(4-Chloro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester
• CAS NO: 17559-40-9
• Molecular Weight: 296.751
• Mol File: 17559-40-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,2R)-1-(4-Chloro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-1-(4-Chloro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester(17559-40-9)
• EPA Substance Registry System: (1S,2R)-1-(4-Chloro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester(17559-40-9)

Safety Data

• Hazardous Substances Data: 17559-40-9(Hazardous Substances Data)

Upstream product

• 5445-25-0 ethyl 2-bromo-2-(4-chlorophenyl)acetate 
• 140-88-5 ethyl acrylate 
• 14062-24-9 4-chloro-benzeneacetic acid, ethyl ester 

Downstream Products

• 56695-75-1 (1R,2S)-1-(4-Chloro-phenyl)-cyclopropane-1,2-dicarboxylic acid 
• 83213-68-7 (1R,5S)-1-(4-chlorophenyl)-3-azabicyclo<3.1.0>hexane 
• 83177-72-4 1-(4-chloro-phenyl)-3-methyl-3-aza-bicyclo[3.1.0]hexane 
• 56815-97-5 1-(p-Chlorphenyl)-cis-cyclopropandicarbonsaeureimid 
• 56695-75-1 (1R,2S)-(+)-1-(4-chlorophenyl)-1,2-cyclopropanedicarboxylic acid 
• 66504-08-3 N-methyl-1-(4-chlorophenyl)-1,2-cyclopropanedicarboxamide 
• 90821-77-5 (1R,5S)-1-phenyl-3-azabicyclo[3.1.0]hexane 
• 90821-76-4 (1S,5R)-1-phenyl-3-azabicyclo<3.1.0>hexane 
• 67644-29-5 1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hexane 
• 83213-69-8 (-)-1-(4-chlorophenyl)-3-azabicyclo<3.1.0>hexane 
• 66504-05-0 (1S,2R)-(-)-1-phenyl-1,2-cyclopropanedicarboximide 
• 66504-37-8 (1R,2S)-(+)-1-phenyl-1,2-cyclopropanedicarboximide 
• 66537-94-8 1-(p-chlorophenyl)-1,2-cyclopropanedicarboximide 
• 66673-12-9 (1R,5S)-1-(4-Chloro-phenyl)-3-aza-bicyclo[3.1.0]hexane-2,4-dione 

Relevant articles and documents

1-Aryl-3-azabicyclohexanes, a New Series of Nonnarcotic Analgesic Agents

A series of 1-aryl-3-azabicyclohexanes was synthesized by hydride reduction of 1-arylcyclopropanedicarboximides.Hydroxyphenyl analogues 20, 22, and 24 were prepared by EtSNa-DMF ether cleavage of the corresponding methoxyphenyl analogues 2m, 2n, and 23, respectively, with the secondary amines 20 and 22 going through the N-formyl intermediates 19 and 21.The p-ethoxy analogue 26 was obtained by O-ethylation of 19, followed by base hydrolysis of the amide 25.The greatest analgesic potency in mouse writhing and rat paw-pain assays was observed for para-substituted compounds.Bicifadine, 1-(4-methylphenyl)-3-azabicyclohexane (2b), was the most potent member of the series and is presently undergoing clinical trials in man.Analgesic activity of 2b is limited to the (+) enantiomer 2v, which has the 1R,5S absolute configuration as determined by single-crystal X-ray analysis.The N-methyl analogue (27d) of 2b showed significant analgesic potency, whereas the N-allyl (27a), N-(cyclopropylmethyl) (27b), and N-(n-hexyl) (27c) analogues were inactive.Bicifadine (2b) showed a nonnarcotic profile different from analogous azabicycloalkane and 3-phenylpyrrolidine analgesics.