457925-19-8

Usage

Molecular Structure

1H-Pyrazole, 4-phenyl-1-[3-(phenylseleno)propyl]is a chemical compound with a five-membered pyrazole ring, a phenyl group, and a 3-(phenylseleno)propyl group attached to it.

Substitution

The pyrazole ring is substituted by a phenyl group and a 3-(phenylseleno)propyl group.

Reactivity

The phenylseleno group, which contains a selenium atom, can impart unique reactivity and selectivity to the compound, making it useful for late-stage functionalization of complex molecules.

Uses

1H-Pyrazole, 4-phenyl-1-[3-(phenylseleno)propyl]is often used in organic synthesis as a building block for pharmaceuticals and agrochemicals. It may be used in various research and manufacturing applications, particularly in the development of new chemical entities and materials.

Toxicity

Selenium-containing compounds can be toxic if mishandled, so it is important to handle 1H-Pyrazole, 4-phenyl-1-[3-(phenylseleno)propyl]- with care.

Upstream product

• 10199-68-5 4-phenyl-1H-pyrazole 
• 122184-76-3 1-iodo-3-(phenylselanyl)propane 
• 852471-30-8 1-[(4-methylphenyl)sulfonyl]-4-phenyl-1H-pyrazole 

Downstream Products

• 10183-74-1 withasomnine 

Relevant academic research and scientific papers

Bu3SnH-mediated radical cyclisation onto azoles

Alkyl radicals have been cyclised onto pyrroles, imidazoles and pyrazoles, and acyl radicals cyclised onto pyrroles, using Bu3SnH-, (TMS)3SiH- and Bu3GeH-mediated aromatic homolytic substitution for the synthesis of bicyclic N-heterocycles. The reactions yield intermediate π-radicals that lose hydrogen in the?rearomatisation step of the aromatic homolytic substitution. Mechanistic studies of these rearomatisation steps indicate aromatic homolytic substitution in which the initiator or breakdown products from the inhibitor are responsible for the H-abstraction step.

Radical cyclisation onto pyrazoles: Synthesis of withasomnine

A novel synthetic protocol for the synthesis of [1,2-b]-fused bicyclic pyrazoles has been developed using radical cyclisation. The protocol uses cyclisation of pyrazole-1-(ω-alkyl) radicals generated from 1-[ω-(phenylselenyl)alkyl]-pyrazole precursors. The pyrazole natural product, withasomnine (3-phenyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole), and larger ring analogues have been synthesised in good yield using the protocol. A Bu3SnH-mediated oxidative cyclisation mechanism is facilitated by azo or Et3B radical initiators acting as oxidants of the intermediate π-radicals.