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関連する概念動画

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.8K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
3.8K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.2K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
5.2K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.7K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
5.7K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.9K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.9K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

8.1K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
8.1K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

6.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
6.6K

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関連する実験動画

Updated: Apr 15, 2026

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

Published on: February 7, 2019

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光学的に活性な1,5-ベンゾチアゼピンに対する簡単な純サイクル添加アプローチ.

Yukihiro Fukata1, Keisuke Asano1, Seijiro Matsubara1

  • 1Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan.

Journal of the American Chemical Society
|April 10, 2015
PubMed
まとめ

研究者らは,1,5-ベンゾチアゼピン合成のための新しい,高度にエナチオセレクティブなサイクル添加法を開発しました. この画期的な発見により,薬の発見と疾患の対抗性研究のための光学的に活性な化合物の効率的な生産が可能になりました.

科学分野:

  • 有機化学 オーガニック・ケミストリー
  • 薬用化学 薬用化学について
  • アシンメトリック・シンセシス

背景:

  • 1,5-ベンゾチアゼピン誘導体は,潜在的な治療用途を持つ薬剤であるとして認識されています.
  • これらの化合物のエナチオセレクティブ合成経路の開発は,薬の開発において極めて重要です.
  • 既存の合成方法は,1,5-ベンゾチアゼピンに対する効率的なエナンチオセレクティブプロトコルがない.

研究 の 目的:

  • 1,5-ベンゾチアゼピン合成のための最初のエナンチオセレクティブサイクロアディションプロトコルの確立.
  • 光学的に活性な1,5-ベンゾチアゼピン誘導体の多様な範囲の簡単な製剤を可能にするために.
  • 生物学的評価のための化合物ライブラリを生成するためのスケーラブルな方法を提供する.

主な方法:

  • キラルイソチオウレア触媒を用いてα,β不飽和アシラモニウム中間産物を生成した.
  • 純 [4 + 3] サイクル加算戦略を採用しました.
  • 2アミノチオフェノールによる2つの連続した化学選択核性攻撃を達成した.

主要な成果:

  • 高い地域選択性を持つ1,5-ベンゾチアゼピンを成功裏に合成した.
  • 様々な基板にわたって良好から優れたステレオ選択性を示した.

さらに関連する動画

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

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関連する実験動画

Last Updated: Apr 15, 2026

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

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

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  • 光学的に活性な1,5-ベンゾチアゼピンのための新しい効率的な合成経路を確立しました.

    • 結論:

    • 開発されたプロトコルは,1,5-ベンゾチアゼピンに対する最初の高度なエナンチオセレクティブの neto [4 + 3] サイクロアディションを表しています.
    • この方法は,光学的に活性な1,5-ベンゾチアゼピンの多様なライブラリを構築するための汎用的なプラットフォームを提供します.
    • この発見は,病気を標的とした将来の薬剤発見の取り組みのための有望な合成戦略を提供します.