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Related Concept Videos

α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

α-Halogenation of Carboxylic Acid Derivatives: Overview

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Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the...
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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Regioselectivity and Stereochemistry of Hydroboration02:36

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Recent Progress in Steroid C(sp3)-H Functionalization.

Agnieszka Wojtkielewicz1, Adam D Majewski2, Zenon Łotowski1

  • 1Faculty of Chemistry, University of Bialystok, Ciolkowskiego 1 K, 15-245, Bialystok, Poland.

Chemical Record (New York, N.Y.)
|November 21, 2024
PubMed
Summary

Selective C-H functionalization offers a powerful route to diverse steroid derivatives for drug discovery and structure-activity relationship studies. This review highlights recent advancements and limitations in creating various C-X steroid analogues.

Keywords:
C−H aminationC−H functionalizationC−H halogenationC−H hydroxylationSteroid

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Methodology

Background:

  • Steroid derivatives are crucial for understanding biological activity and developing new drugs.
  • Efficient synthesis of steroid analogues is essential for structure-activity relationship (SAR) studies.
  • Selective C-H functionalization presents a promising strategy for accessing diverse steroid scaffolds.

Purpose of the Study:

  • To review recent advances in selective C-H functionalization of steroids.
  • To highlight methods for synthesizing various C-X (C-O, C-C, C-N, C-S, C-halogen) steroid derivatives.
  • To discuss the scope and limitations of current C-H functionalization techniques in steroid chemistry.

Main Methods:

  • Review of literature on recent steroid C-H functionalization reactions.
  • Categorization of C-H functionalization based on the type of C-X bond formed.
  • Analysis of reported synthetic methodologies, including catalysts and reaction conditions.

Main Results:

  • Demonstrated versatility of C-H functionalization for creating diverse steroid analogues.
  • Examples of successful C-O, C-C, C-N, C-S, and C-halogen bond formation on steroid skeletons.
  • Identification of key methods and their applicability across different steroid systems.

Conclusions:

  • Selective C-H functionalization is a valuable tool for steroid derivative synthesis.
  • Advances in this field facilitate SAR studies and the discovery of biologically active compounds.
  • Further development is needed to overcome limitations and expand the scope of these methods.