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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

12.1K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
12.1K
The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry07:02

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry

14.2K
A simple two-step approach involving rubber modification and cross-linking yields fully reworkable, elastic rubber products.
14.2K
Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors01:31

Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors

5.8K
The Diels–Alder reaction is thermally reversible, meaning that the reaction reverts to the starting diene and dienophile under suitable temperatures. The forward reaction gives a cyclohexene derivative and is favored at low to medium temperatures. The reverse process, also called retro-Diels–Alder reaction, is a ring-opening process favored at high temperatures.
5.8K
Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging10:47

Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging

9.2K
The bioorthogonal inverse electron demand Diels-Alder cycloaddition has been harnessed to create an effective and modular pretargeted PET imaging strategy for cancer. In this protocol, the steps of this methodology are described in the context of a model system employing the colorectal cancer targeted antibody huA33 and a 64Cu-labeled radioligand.
9.2K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

5.1K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
5.1K
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

7.2K
In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction. 
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
7.2K

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関連する実験動画

Updated: Jan 19, 2026

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
07:02

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry

Published on: August 25, 2016

14.2K

ディエルス-アルダーサイクロアディションによる多用途ペプチドマクロサイクリング

Jeffrey E Montgomery, Justin A Donnelly, Sean W Fanning

    Journal of the American Chemical Society
    |September 17, 2019
    PubMed
    まとめ
    この要約は機械生成です。

    ディエルス-アルダーサイクライゼーションは,ペプチドを安定させ,薬のような性質を高めるための多用途な方法を提供します. このアプローチは,治療用途のプロテアゼ耐性および生物学的活性を改善します.

    さらに関連する動画

    [4+2] Cycloaddition of Conjugated Dienes: Diels&amp;#8211;Alder Reaction
    01:16

    [4+2] Cycloaddition of Conjugated Dienes: Diels&#8211;Alder Reaction

    12.1K
    Diels&amp;#8211;Alder vs Retro-Diels&amp;#8211;Alder Reaction: Thermodynamic Factors
    01:31

    Diels&#8211;Alder vs Retro-Diels&#8211;Alder Reaction: Thermodynamic Factors

    5.8K

    関連する実験動画

    Last Updated: Jan 19, 2026

    The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
    07:02

    The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry

    Published on: August 25, 2016

    14.2K
    [4+2] Cycloaddition of Conjugated Dienes: Diels&amp;#8211;Alder Reaction
    01:16

    [4+2] Cycloaddition of Conjugated Dienes: Diels&#8211;Alder Reaction

    12.1K
    Diels&amp;#8211;Alder vs Retro-Diels&amp;#8211;Alder Reaction: Thermodynamic Factors
    01:31

    Diels&#8211;Alder vs Retro-Diels&#8211;Alder Reaction: Thermodynamic Factors

    5.8K

    科学分野:

    • 薬剤化学
    • 有機化学
    • 生物化学

    背景:

    • マクロサイクリングは,分子構造を先行組織化することによってペプチド薬の性質を高めます.
    • ペプチド安定化のための既存の方法は,範囲と適用において制限があります.

    研究 の 目的:

    • ペプチドのマクロサイクリングと安定化のための新しい戦略としてダイエルス-アルダー [4 + 2]サイクロアディションを探求する.
    • ペプチドの構造的剛性,プロテアゼ抵抗性,および生物学的活性に対するディエルス-アルダーサイクル化の影響を評価する.

    主な方法:

    • ディエルス-アルダー反応は,固体相および水相条件で様々なペプチド基板で実施された.
    • ペプチド構造とステレオ化学を分析するために,NMRスペクトロスコーピーと分子動力学シミュレーションを使用した.
    • コクリスタログラフィーは,標的と結合した安定化ペプチドの構造を決定するために使用された.

    主要な成果:

    • 安定したペプチド構造を形成する.
    • 反応は調整可能なステレオ化学制御を示し,エンドアダクトを好む.
    • Diels- Alderのサイクリングペプチドは,プロテアゼ抵抗性の増加と生物学的活性性の強化を示した.
    • 構造分析により,エンドステレオ化学と標的結合への貢献が確認された.

    結論:

    • ディエルス-アルダーサイクリングは,多様なペプチド構造モチーフを安定させるための多機能かつ効果的な方法である.
    • この化学反応はペプチドの薬理学的特性を高め,薬の開発に有望な道を示しています.
    • ダイエルス-アルダー誘導体のユニークな構造は,標的結合相互作用に直接貢献することができます.