138163-09-4

Basic information

• Product Name: 1-Piperidinecarboxylic acid, 4-ethenyl-, phenylmethyl ester
• CAS NO: 138163-09-4
• Molecular Formula: C15H19NO2
• Molecular Weight: 245.321
• Mol File: 138163-09-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-Piperidinecarboxylic acid, 4-ethenyl-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinecarboxylic acid, 4-ethenyl-, phenylmethyl ester(138163-09-4)
• EPA Substance Registry System: 1-Piperidinecarboxylic acid, 4-ethenyl-, phenylmethyl ester(138163-09-4)

Safety Data

• Hazardous Substances Data: 138163-09-4(Hazardous Substances Data)

Usage

Chemical class

piperidine

Uses

precursor in the synthesis of pharmaceuticals and other organic compounds

Reactivity

ability to react with a variety of other chemicals

Handling precautions

can be hazardous if not used properly

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 138163-08-3 N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 1119-22-8 divinyl zinc 

Downstream Products

• 138163-10-7 (RS)-3-bromo-5-(1-benzyloxycarbonyl-4-piperidyl)-2-isoxazoline 
• 138163-11-8 (RS)-3-benzyloxy-5-(1-benzyloxycarbonyl-4-piperidyl)-2-isoxazoline 

Relevant articles and documents

Decarboxylative Negishi Coupling of Redox-Active Aliphatic Esters by Cobalt Catalysis

A cobalt-catalyzed decarboxylative Negishi coupling reaction of redox-active aliphatic esters with organozinc reagents was developed. The method enabled efficient alkyl–aryl, alkyl–alkenyl, and alkyl–alkynyl coupling reactions under mild reaction conditions with no external ligand or additive needed. The success of an in situ activation protocol and the facile synthesis of the drug molecule (±)-preclamol highlight the synthetic potential of this method. Mechanistic studies indicated that a radical mechanism is involved.

Analogues of the low-efficacy partial GABAA agonist 4-PIOL. Syntheses and in vitro pharmacological studies

4-PIOL (3-hydroxy-5-(4-piperidyl)isoxazole) is a low-efficacy GABAA agonist showing a dominating GABAA antagonist profile.Three dihydro analogues of 4-PIOL were synthesized, including (RS)-3-hydroxy-5-(4-piperidyl)-2-isoxazoline (1).The synthesis of 1 was based on a regioselective 1,3-dipolar cyclo-addition reaction between 1-benzyloxycarbonyl-4-vinylpiperidine (7) and bromonitrile oxide, prepared in situ from dibromoformoxime.Furthermore, the spiro analogues of 1 3-hydroxy-1-oxa-2,8-diazaspirodec-2-ene (2) and (RS)-3-hydroxy-1-oxa-2,7-diazaspirodec-2-ene (3) were synthesized regiospecifically via cycloaddition of bromonitrile oxide to the N-benzyloxycarbonyl-protected forms of 4-methylenepiperidine (11) and 3-methylenepiperidine (15) respectively.In contrast to 4-PIOL, none of the new compounds 1-3 showed detectable effects on the binding of 3H-GABAA or the subunit-selective GABAA agonist, 3H-THIP, to GABAA receptor sites, and they did not significantly affect the muscimol-stimulated binding of 3H-diazepam to the benzodiazepine site of the GABAA receptor complex.