83249-11-0

Usage

Uses

Used in Pharmaceutical Industry:
1-phenylbicyclo<1.1.1>pent-3-ylamine hydrochloride is used as a research chemical for the development of potential treatments for psychological and neurological disorders. Its stimulant properties and structural similarities to other psychoactive substances make it a valuable compound for understanding the mechanisms of action and potential therapeutic effects in these conditions.
Used in Scientific Research:
In the field of neuroscience, 1-phenylbicyclo<1.1.1>pent-3-ylamine hydrochloride serves as a research tool to explore the effects of psychoactive substances on the central nervous system. Its psychoactive properties allow scientists to investigate the interactions between these compounds and the brain, potentially leading to advancements in our understanding of neurological disorders and the development of new treatments.
Used in Drug Development:
1-phenylbicyclo<1.1.1>pent-3-ylamine hydrochloride is utilized in the process of drug development, where it can be tested for its efficacy and safety in treating specific disorders. Its psychoactive nature and stimulant effects make it a candidate for further investigation into its potential as a therapeutic agent for various conditions.
Note: The uses mentioned above are based on the potential applications of 1-phenylbicyclo<1.1.1>pent-3-ylamine hydrochloride as a research chemical and should not be construed as an endorsement or recommendation for its use in any specific context. The safety and efficacy of 1-phenylbicyclo<1.1.1>pent-3-ylamine hydrochloride in humans have not been established, and further research is required to determine its appropriate applications.

Upstream product

• 83249-09-6 methyl 3-phenylbicyclo<1.1.1>pentane-1-carboxylate 
• 65862-03-5 methyl 3-phenyl-2,2-dichlorobicyclo<1.1.1>pentanecarboxylate 
• 83249-04-1 3-phenylbicyclo<1.1.1>pentane-1-carboxylic acid 

Downstream Products

• 83249-12-1 3-nitro-1-phenylbicyclo<1.1.1>pentane 

Relevant academic research and scientific papers

Radical Multicomponent Carboamination of [1.1.1]Propellane

Three-dimensional, small-ring scaffolds are very important in modern drug discovery to expand the available drug-like chemical space and to optimize drug candidates. Among them, bicyclo[1.1.1]pentane (BCP) is regarded as a high-value bioisostere for a phenyl ring or tert-butyl group; it provides an option to generate drug-like molecules with good passive permeability, high aqueous solubility, and improved metabolic stability, though the lack of methodology to functionalize BCP remains a significant challenge. Here we present an efficient method, developed with the aid of density functional theory calculations, for the synthesis of multifunctionalized BCP derivatives by means of a radical multicomponent carboamination of [1.1.1]propellane. This reaction features mild conditions, one-pot operation, and gram-scale synthetic capability, and opens up a unique and highly efficient route for the synthesis of multifunctionalized BCP derivatives, including synthetically useful 3-substituted BCP-amines.

Bicyclo[1.1.1]pentane-Derived Building Blocks for Click Chemistry

Syntheses of bicyclo[1.1.1]pentane-derived azides and terminal alkynes – interesting substrates for click reactions – are described. With a few exceptions, these compounds were prepared in two or three steps starting from common synthetic intermediates – the corresponding carboxylic acids. The key step in the synthesis of 1-azidobicyclo[1.1.1]pentanes is a copper-catalysed diazo-transfer reaction with imidazole-1-sulfonyl azide. The preparation of bicyclo[1.1.1]pentyl-substituted alkynes relies on a Seyferth–Gilbert homologation with dimethyl 1-diazo-2-oxopropylphosphonate (Ohira–Bestmann reagent). Both types of target compounds were found to be suitable substrates for click reactions, and thus they are promising building blocks for medicinal, combinatorial and bioconjugate chemistry. A practically important side result of this study was a multigram preparation of Boc-monoprotected 1,3-diaminobicyclo[1.1.1]pentane – a representative bicyclic conformationally restricted diamine derivative.

Polar Substituent Effects in 1,3-Disubstituted Bicyclopentanes

The pKa's of eight 3-substituted bicyclopentanecarboxylic acids have been measured and found to correlate well with ?I constants.The value of ρI (2.23 +/- 0.12) is large but not large enough to propose any special perturbation of normal field-inductive effects by the close proximity (about 1.88 Ae) of the bridgehead carbons.Also determined were the products and rates of solvolyses of the p-nitrobenzoates of three 3-substituted 1-pentanes.The products were primarily unrearranged, and the rates again showed no surprisingsubstituent effects.A practical synthesis of 1,3-disubstituted bicyclopentanes has been developed and is described.