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Development of Novel Bicyclopentanes (BCP) Bioisosteres From Bench Stable [1.1.1]-Propellane Precursors PhD
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Development of Novel Bicyclopentanes (BCP) Bioisosteres From Bench Stable [1.1.1]-Propellane Precursors PhD
Loughborough University, Loughborough, United Kingdom
# 301-350QS Subject Rankings
36 monthsProgram duration
YesScholarships
ChemistryMain Subject Area
Program overview
Main Subject
Chemistry
Degree
PhD
Study Level
PHD
Study Mode
On Campus
Bicyclo-[1.1.1]-pentanes (BCPs) are an exciting class of strained, sp3 rich carbon. While their initial use was in the materials sector, recent impact...
Read more has been in medicinal chemistry, drug development and the agrochemical sector. Their appeal is due to a unique 3-D structure, a direct consequence of its high sp3 carbon content, and has led to its use as a bioisosteres for the tert-butyl group, internal alkynes and significantly, mono- and disubstituted arenes.
Their synthesis is accomplished using hetero- or homolytic cleavage and relies on the inherent strain in the central carbon-carbon bond of [1.1.1]-propellane. However, the practical isolation and storage of [1.1.1]-propellane is very problematic; it is isolated as a solution in ethereal solvents, it must be cryogenically stored, and should be used before its rapid degradation.
In this project we will pioneer a stable crystalline alternatives of [1.1.1]-propellane. Functionalization will be explored using several nucleophiles, providing orthogonal 1,3-disubstituted-[1.1.1]-bicyclopentane (BCP) precursors amenable to subsequent cross-coupling reactions (e.g., transition metal and photoredox mediated). This methodology will provide a superior synthetic approach to 1,3-disubstituted BCPs, with far less waste, as well as delivering stable crystalline BCP precursors.
This project will significantly increase the synthetic scope of BCPs compared to current strategies, as well as providing an excellent training platform to the prospective PhD candidate in our new state-of-the-art laboratories here at Loughborough. Read less
Program overview
Main Subject
Chemistry
Degree
PhD
Study Level
PHD
Study Mode
On Campus
Bicyclo-[1.1.1]-pentanes (BCPs) are an exciting class of strained, sp3 rich carbon. While their initial use was in the materials sector, recent impact...
Read more has been in medicinal chemistry, drug development and the agrochemical sector. Their appeal is due to a unique 3-D structure, a direct consequence of its high sp3 carbon content, and has led to its use as a bioisosteres for the tert-butyl group, internal alkynes and significantly, mono- and disubstituted arenes.
Their synthesis is accomplished using hetero- or homolytic cleavage and relies on the inherent strain in the central carbon-carbon bond of [1.1.1]-propellane. However, the practical isolation and storage of [1.1.1]-propellane is very problematic; it is isolated as a solution in ethereal solvents, it must be cryogenically stored, and should be used before its rapid degradation.
In this project we will pioneer a stable crystalline alternatives of [1.1.1]-propellane. Functionalization will be explored using several nucleophiles, providing orthogonal 1,3-disubstituted-[1.1.1]-bicyclopentane (BCP) precursors amenable to subsequent cross-coupling reactions (e.g., transition metal and photoredox mediated). This methodology will provide a superior synthetic approach to 1,3-disubstituted BCPs, with far less waste, as well as delivering stable crystalline BCP precursors.
This project will significantly increase the synthetic scope of BCPs compared to current strategies, as well as providing an excellent training platform to the prospective PhD candidate in our new state-of-the-art laboratories here at Loughborough. Read less
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QS subject rankings
Subject: Chemistry
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Development of Novel Bicyclopentanes (BCP) Bioisosteres From Bench Stable [1.1.1]-Propellane Precursors PhD
Digital Twins for Biofilm Management PhD
Dispersionless Integrable Systems In 2+1 Dimensions PhD
Social Sciences and Management (5)
An Evaluation of Erasmus+ Sport Projects and Their Impact on EU Sport Policy Development PhD
An Evaluation of Erasmus+ Sport Projects and Their Impact on EU Sport Policy Development PhD
Climate Change, Work Design and Worker Wellbeing Phd
Climate Change, Work Design and Worker Wellbeing Phd
Communication and Social Change (CSC) Hub Studentship PhD
Communication and Social Change (CSC) Hub Studentship PhD
Enhancing Motivation in Sport and Exercise Contexts PhD
Enhancing Motivation in Sport and Exercise Contexts PhD
Out of School Youth Provision: An Analysis of Funding and Operational Resilience within the Sector PhD
Out of School Youth Provision: An Analysis of Funding and Operational Resilience within the Sector PhD