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Constitutional Isomers of Alkanes02:18

Constitutional Isomers of Alkanes

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Organic compounds of the same molecular formula can have different structural formulas called constitutional isomers, and the phenomenon is known as constitutional isomerism. Alkanes with four or more carbons showing multiple structures with the same molecular formula thereby exhibit constitutional isomerism.
The linear isomer of an alkane is prefixed by the term “n”; hence a linear isomer of pentane is known as n-pentane. Based on the type of branching, some of the...
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Organic Compounds03:02

Organic Compounds

57.9K
All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
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¹H NMR Chemical Shift Equivalence: Homotopic and Heterotopic Protons01:03

¹H NMR Chemical Shift Equivalence: Homotopic and Heterotopic Protons

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Protons in identical electronic environments within a molecule are chemically equivalent and have the same chemical shift. The replacement test is a useful tool to identify chemical equivalence and predict NMR spectra. A substituent replaces each of the protons being examined and the resulting molecules are compared. If the same molecule is obtained, the protons are equivalent or homotopic. Replacement of any hydrogens in ethane by chlorine yields chloroethane because all six protons are...
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Prochirality02:05

Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Nomenclature of Alkanes02:22

Nomenclature of Alkanes

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In the late 19th-century, the number of new chemical compounds discovered increased tremendously. Hence, the necessity arose to develop a naming system for the systematic nomenclature of these newly discovered compounds. IUPAC (International Union for Pure and Applied Chemistry), established in 1919, sets rules for the nomenclature.
The alkane nomenclature considers the length of the carbon chain, the number, and the location of the substituent to arrive at its systematic name. The IUPAC...
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Updated: Feb 28, 2026

Cellular Lipid Extraction for Targeted Stable Isotope Dilution Liquid Chromatography-Mass Spectrometry Analysis
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Hetero[3.1.1]propelanos

Rebecca I Revie1, Ayan Dasgupta1, Yasmine Biddick1

  • 1Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, UK.

Nature chemistry
|February 25, 2026
PubMed
Resumen
Este resumen es generado por máquina.

Los investigadores desarrollaron una síntesis unificada de heterociclos [3.1.1]propelanos, precursores cruciales para nuevos bloques de construcción en el diseño de fármacos. Estos compuestos permiten la creación de diversos heterociclos puentes bicíclicos con propiedades mejoradas.

Palabras clave:
heterociclospropelanossíntesisdescubrimiento de fármacosquímica medicinalquímica orgánicaquímica sintética

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Área de la Ciencia:

  • Química Orgánica
  • Química Medicinal
  • Química Sintética

Sus antecedentes:

  • [n.1.1]Los propelanos son precursores vitales de los biciclo[n.1.1]alcanos, valorados en el diseño de fármacos como bioisósteros del anillo de benceno.
  • Los análogos heterocíclicos ofrecen potencial para perfiles fisicoquímicos superiores en comparación con las versiones carbocíclicas.

Objetivo del estudio:

  • Desarrollar una síntesis unificada para heterociclos [3.1.1]propelanos que contienen heteroátomos de oxígeno, nitrógeno y azufre.
  • Explorar la utilidad de estos novedosos propelanos en la síntesis de heterociclos puentes bicíclicos.

Principales métodos:

  • Síntesis de un precursor común mediante ciclopropanación catalizada por rodio a escala multigramo.
  • Desarrollo de rutas sintéticas distintas para hetero[3.1.1]propelanos, diferentes de los análogos carbocíclicos.
  • Reacciones de apertura de anillo radicalarias de los hetero[3.1.1]propelanos sintetizados.

Principales resultados:

  • Síntesis unificada exitosa de una familia de heterociclos [3.1.1]propelanos.
  • Se demostraron enfoques sintéticos distintos en comparación con los propelanos carbocíclicos.
  • Se generó una variedad de heterociclos puentes a través de reacciones de apertura de anillo radicalarias.

Conclusiones:

  • Los métodos desarrollados proporcionan acceso a novedosos heterociclos [3.1.1]propelanos.
  • Estos compuestos sirven como precursores versátiles para programas de descubrimiento de fármacos.
  • Los heterociclos puentes sintetizados poseen una alta utilidad en química medicinal.