77053-85-1

Basic information

• Product Name: 1,2-Cyclopropanedicarboxylic acid, 1-[4-(1,1-dimethylethyl)phenyl]-, cis-
• CAS NO: 77053-85-1
• Molecular Formula: C15H18O4
• Molecular Weight: 262.306
• Mol File: 77053-85-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,2-Cyclopropanedicarboxylic acid, 1-[4-(1,1-dimethylethyl)phenyl]-, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Cyclopropanedicarboxylic acid, 1-[4-(1,1-dimethylethyl)phenyl]-, cis-(77053-85-1)
• EPA Substance Registry System: 1,2-Cyclopropanedicarboxylic acid, 1-[4-(1,1-dimethylethyl)phenyl]-, cis-(77053-85-1)

Safety Data

• Hazardous Substances Data: 77053-85-1(Hazardous Substances Data)

Upstream product

• 77053-60-2 methyl 2-bromo-2-(4-tert-butylphenyl)ethanoate 
• 3549-23-3 methyl 2-(4-tert-butylphenyl)acetate 
• 77062-89-6 (1R,2S)-1-(4-tert-Butyl-phenyl)-cyclopropane-1,2-dicarboxylic acid dimethyl ester 

Downstream Products

• 86215-71-6 1-(4-(tert-butyl)phenyl)-3-azabicyclo[3.1.0]hexane 
• 77053-90-8 1-(p-tert.-butylphenyl)-1,2-cyclopropanedicarboximide 

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.