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関連する概念動画

Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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,...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Naming Enantiomers02:21

Naming Enantiomers

The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three steps:...
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
Prochirality02:05

Prochirality

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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関連する実験動画

Updated: Jun 15, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

[3]ロタキサンにおける配列イソメリズム

Anne-Marie L Fuller1, David A Leigh, Paul J Lusby

  • 1School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh, EH9 3JJ United Kingdom.

Journal of the American Chemical Society
|March 17, 2010
PubMed
まとめ

研究者は,ロタキサン糸のマクロサイクルを精密に配列する新しい方法を開発しました. この技術は,マクロサイクルの順序を機械的にロックして,制御された分子組立を可能にすることで,明確なステレオアイソマーを作成します.

科学分野:

  • 超分子化学 超分子化学
  • オーガニック・シンセシス オーガニック・シンセシス
  • マテリアルサイエンス 材料科学

背景:

  • 分子構成要素の精密な配列組み立ては,複雑な機能アーキテクチャを作成するために不可欠です.
  • 相互に絡み合った分子構造であるロタキサンは,機械的な制御と情報保存のユニークな可能性を秘めています.
  • 単一の分子糸上の複数のマクロサイクルの配列を制御することは,合成の課題です.

研究 の 目的:

  • 異なるマクロサイクルを非対称的なロタキサン糸に順次,制御された組み立てのための一般的な戦略を開発する.
  • 機械的に指示されたマクロサイクル配列による[3]ロタキサンジアステロエーマーの合成を実証する.
  • 前もって決定された構造的配置を持つ複雑な多環ロタキサンを作る可能性を調査する.

主な方法:

  • パラジウム (((II) ピリジン-2,6-ジカルボキシアミド複合体の反復調整により,ロタキサン糸のピリジンリガンドに.
  • マクロサイクルは,各マクロサイクルを確保するために,環閉オレフィンメタテシスによるマクロサイクリング.
  • パラジウム (II) テンプレートを順次除去することで,その後の複合化とマクロサイクリングが可能になり,正確な配列を保証します.

主要な成果:

  • マクロサイクルの配列だけで異なる2つの[3]ロタキサン・ダイアステロエーマーを合成した.

さらに関連する動画

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

関連する実験動画

Last Updated: Jun 15, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

  • マクロサイクルの配置に対する機械的な制御の実証,アトロピソメリズムと同様のステレオアイソメリズムにつながります.
  • 既定のマクロサイクルのシーケンスを持つ多環ロタキサンを構築するための方法の確立.

    • 結論:

    • 記述された戦略は,ロタキサン糸のマクロサイクルの組立に対する正確な連続制御を提供します.
    • この方法は,機械的に強制されたステレオ化学を用いた複雑なロタキサン構造の合成を可能にします.
    • この発見は,洗練された分子機械や特性を合わせた材料を設計するための道を開く.