215124-73-5

Basic information

• Product Name: 1,2,3,4-tetrahydro-4-allyl-1,5-dimethyl-4-(3-methoxyphenyl)pyridine
• CAS NO: 215124-73-5
• Molecular Weight: 257.376
• Mol File: 215124-73-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,2,3,4-tetrahydro-4-allyl-1,5-dimethyl-4-(3-methoxyphenyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-tetrahydro-4-allyl-1,5-dimethyl-4-(3-methoxyphenyl)pyridine(215124-73-5)
• EPA Substance Registry System: 1,2,3,4-tetrahydro-4-allyl-1,5-dimethyl-4-(3-methoxyphenyl)pyridine(215124-73-5)

Safety Data

• Hazardous Substances Data: 215124-73-5(Hazardous Substances Data)

Upstream product

• 4629-80-5 1,3-dimethyl-4-piperidinone 
• 31600-88-1 m-methoxyphenyllithium 
• 123004-53-5 1,3-dimethyl-4-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine 
• 106-95-6 allyl bromide 

Downstream Products

• 88550-29-2 N-methyl-9α-methyl-5-(3-hydroxyphenyl)morphan 

Relevant articles and documents

N-Substituted 9beta-methyl-5-(3-hydroxyphenyl)morphans are opioid receptor pure antagonists.

The inhibition of radioligand binding and [35S]GTPgammaS functional assay data for N-methyl- and N-phenethyl-9beta-methyl-5-(3-hydroxyphenyl)morphans (5b and 5c) show that these compounds are pure antagonists at the micro, delta, and kappa opioid receptors. Since 5b and 5c have the 5-(3-hydroxyphenyl) group locked in a conformation comparable to an equatorial group of a piperidine chair conformation, this information provides very strong evidence that opioid antagonists can interact with opioid receptors in this conformation. In addition, it suggests that the trans-3, 4-dimethyl-4-(3-hydroxyphenyl)piperidine class of antagonist operates via a phenyl equatorial piperidine chair conformation. Importantly, the close relationship between the 4-(3-hydroxyphenyl)piperidines and 5-(3-hydroxyphenyl)morphan antagonists shows that the latter class of compound provides a rigid platform on which to build a novel series of opioid antagonists.

A stereoselective synthetic approach to N-alkyl-4β-methyl-5- phenylmorphans

A convergent, highly stereoselective synthetic approach to N-alkyl-4β- methyl-5-phenylmorphans has been developed utilizing alkylation of the metalloenamine of N-alkyl-1,2,3,6-tetrahydro-4-phenylpyridines with 2- (chloromethyl)-3,5-dioxahex-1-ene (Okahara's reagent) followed by Clemmensen reduction.